Voiced by: Gerry Rosenthal

• Abusive Parents: His biological dad abandoned him at a young age and his mother is a narcissistic parent who's married several men in the past. His mom chooses to dump Jimmy at various schools rather than get to the root of his problems and deal with them. His tough exterior and self-reliance is a result of years of emotional neglect and the need to defend himself from other people.
• Acquired Situational Narcissism: After triumphing over all the cliques and effectively taking over the school, Jimmy practically becomes Drunk with Power, talking about how great he is and surrounding himself with yes-men who keep complimenting him while brushing off Petey's concerns. It's a far cry from his much more down-to-earth personality beforehand. However, once his popularity takes a tumble he snaps back to normal.
  Jimmy: Not now, Pete, I'm basking in adulation. (...) The court must know their king.
• Action Genre Hero Guy: Jimmy hits almost every beat, being a tough-as-nails bald white male with a buzz-cut who prefers punching out his enemies.
• Anti-Hero: Of the "Pragmatic" variety. While Jimmy isn't very nice, thanks to a bad upbringing, he's only defending himself from those who are out to bully or hurt him. Story-wise, he's standing up for weaker kids, aligning with outcasts, and his quest to take over the school is to simply stop the rampant bullying and violence from the 5 main cliques. He also helps those who are kind to him and on one occasion ran into a burning building to save some kids who were trapped inside.
• Armoured Closet Gay: Downplayed. Jimmy is bisexual and can optionally kiss boys, but makes homophobic remarks about the Jocks and denies being "sexually confused" to Pinky during their date.
• Ax-Crazy: Frequently accused of being a psychopath for his violent tendencies and overall aggressiveness. How true it is may vary a bit based on gameplay but story-wise he's usually a subversion. He certainly gets a kick out of putting down chapter bosses and other jerks but he pointedly needs a good reason to fight and is even annoyed by meaningless, easily avoidable conflict. Tellingly, he's frustrated when Russell gets tricked into fighting him at the end of Chapter 1, calling it a "waste of time". Most of the time, it seems like he'd rather have people leave him alone.
• Badass in a Nice Suit: If the player makes him wear any of the clothing from Aquaberry's outlet store.
• Bald Head of Toughness: He's a Bully Hunter who takes on every clique at his new boarding school as a One-Man Army in order to end the rampant bullying, aided by his natural Made of Iron disposition as he's capable of shrugging off bats broken over his head, a sledgehammer hit that sends him flying, and even blows from a prized boxing champion. His default hairstyle is a ginger buzz cut, likely enforced from one of the previous schools he's been expelled from. The player can take this further in-game by making him completely bald or subvert the trope by allowing him to grow his hair out.
• Bare-Fisted Monk: He fights with his fists only and has no techniques when he comes into Bullworth. At the end of the game, he learns military-style fighting, kicks, roundhouse kicks, leg sweeps, grapples, two nasty Groin Attack moves, headbutts, etc.
• Big Man on Campus: Officially elevated to this in the penultimate chapter and again at the end of the game: schmoozing with the ladies, surrounded by an entourage, and letting loose a few Tom Cruise gestures because he's just that awesome.
• Boisterous Bruiser: Especially when he's done kicking any chapter bosses' asses. He even forces them to say who's the boss, and if you didn't know who, it's Jimmy Hopkins.
  Jimmy: Who won?! Me! Jimmy Hopkins! That's who! Who won?!
  Hal: ...you...
  Jimmy: Who?! (Chokes)
  Hal: Jimmy. Hopkins.
  Jimmy: CORRECT!
• Book Dumb: Downplayed, but it's implied that he's canonically not known well for his academic prowess. Miss Peters, the music teacher, blackmails him into starring in the school play by not assigning him another F in her class. He also doesn't know what a "sociopath" or "hermaphrodite" are. You can avert this in normal gameplay and it is somewhat justified why he would be good at some of his classes as they are either relevant to the items he uses throughout the game or he actually likes the teacher and therefore puts more effort into the lesson.
• Brats with Slingshots: He steals one from Davis in "The Setup" after he was shot by Davis with it. Jimmy later earns an upgraded wrist rocket (a metal slingshot with a wrist wrap and scope) in "The Candidate".
• Break the Haughty: Loves doing this. He grabs Derby by the hair and forces him to say Jimmy's name, chokes Hal and makes him do the same thing and throws him onto the hard concrete when he does, and yells and brags at the knocked out bodies of the school Football team after a hard ass kicking. But then Jimmy's haughtiness breaks when the school's many subcultures and factions turn on him.
• Brilliant, but Lazy: For all his past delinquent actions and all the various ways he can get in trouble during the game, Jimmy is also more than capable of passing, even excelling in all of his classes.
• Bruiser with a Soft Center: Jimmy is no stranger to combat and will jump into the fight when someone attacks him. However, it's suggested that his combative nature is a product of his home life as he has never had a healthy relationship with a paternal figure. His mother is also too self-absorbed to put his needs above her own and, rather than try to resolve his issues, she dumps him at a school so he can be someone else's problem. When Petey manages to get through to his softer side, Jimmy is revealed to be a loyal friend who, while not above violence, uses his fists to stand up for the little guy.
• Bully Hunter: He's particularly disgusted with how lower caste students prey on each other, rather than face the might of the preps, jocks, and others. As he said to Russell, "There are bunch of kids around this place who need a beating, and you're picking on the few who don't."
• The Casanova: Given that he's able to get the attention of 8 girls by the end of the game, and six guys too. (His mojo fails on the art teacher, however.)
• Casanova Wannabe: At the beginning of the game, story moments aside, Jimmy's lines when flirting with the girls are less than stellar, often stumbling his lines and using wimpy or bad pick-up lines. Progressing through Art class lets him grow out of this, with the final class removing the requirement of giving gifts to them completely.
• The Cassandra: Jimmy totally lacks Gary's incredible gift of being able to get others to listen through words alone. Almost every attempt he makes to solve issues with others through talking ends in a fight.
• Character Development: Begins the game as a standoffish and hostile jerk, but makes friends with Gary and Petey quickly. He's also initially content to just ride out the schoolyear and pull the occasional prank, but when Gary betrays him, he resolves to unify the school and stop all the bullying out of self-interest and a genuine desire to do good. As he gets more entangled with the different cliques and their personal drama, he also begins to show a more empathetic side, particularly to the girls. When he becomes king of the school, he gets some serious Acquired Situational Narcissism and begins lording his popularity and fame over the rest of his friends, which blinds him to Gary's imminent attack. When all of his fame and popularity is stripped away, Jimmy remembers why he became a Bully Hunter in the first place and fights back against Gary to save the school. He also rewards Petey and Zoe for their help, showing that he's at least somewhat grown out of his selfish ways.
• Chick Magnet: During the main story mode, Jimmy manages to win the affection of several girls in the school, like Beatrice, Pinky, Lola, Mandy, and Zoe, which earns Jimmy a photo of each of them that decorates his room, after the player completes a mission that focus on them.
• Clint Squint: It's a wonder he can even see though those slits.
• Combat Pragmatist: Jimmy can explore many ways to take down an opponent, ranging from a simple punch in the face to using a freaking bottle rocket launcher to paste someone from a distance.
• Cool Board: He gets a skate board as a Thank-You present from Bucky in "Defend Bucky". And he's the only one to use a skateboard in the whole town.
• Covered in Scars: Jimmy's dome is marred by a few scars, which disappear if you grow his hair out.
• Cultured Badass: Art classes show that Jimmy has a surprising gift for oil painting.
• Custom Uniform: For some reason, he and Petey are the only students who wear bright blue uniform vests. The Nerds and the Non-Clique Students respectively wear kelly green and dark teal sweater vests, and Gary has a unique teal vest. The other cliques don't wear school sweater-vests.
  • In beta screenshots, the Non-Clique Students wore blue vests the same color as Jimmy's. It's probable that they were switched to dark teal to make Jimmy stand out more.
• Cutscene Incompetence: Whenever Gary's around, Jimmy seems to lose the ability to do anything besides clench his fists, scuff his feet, and huff. However, this is justified by the fact that he's still trying to figure out why Gary felt the need to betray him despite doing nothing to deserve it. In the final mission, Jimmy finally confronts Gary and his first question is "Why did you do it?" and he's completely disgusted when Gary tells him that he betrayed him because he enjoys the feeling of being in power and because he saw Jimmy as a threat.
• Deadpan Snarker: Hopkins' dry brand of humor, which is helped enormously by him being the Great Stone Face of Bullworth Academy. He especially enjoys running fast ones past the Headmaster (criticizing his dress sense among other things), even during his expulsion proceeding.
  Crabblesnitch: Very droll! A comedian to the end. Well, you are going to have to take your comedic talents elsewhere.
• Defrosting Ice King: He grows from an aggressive outcast who openly distrusts others, to the popular kid who helps the helpless when they are beaten down or abused.
• Disappeared Dad: No mention is made of his birth/biological father, only that he has had many stepfathers.
• Disappointed by the Motive: Ever since Gary betrayed Jimmy in the first chapter, Jimmy has been deeply confused about why Gary would do something like this to a friend. When confronted during the final showdown, Jimmy is angry and bewildered that Gary would betray him out of paranoia and to feel powerful.
• Dude, Where's My Respect?: By becoming the school's most powerful leader, he unwittingly becomes a whipping boy for everything that goes wrong. Jimmy tries his best to maintain order, but he's rearranging the deckchairs on the Titanic by that point.
• Eagleland: Probably sums it up best when he's giving a Rousing Speech to the Townies, convincing them to help him stop the all-out brawl at Bullworth Academy in "Complete Mayhem".
  Jimmy: This is America! We go in there with threats and bribes until we get what we want. If all else fails, we beat the crap out of everyone!
• Establishing Character Moment: Insults and disrespects his stepdad, a person with a position with authority over Jimmy. However, then he displays anger and sadness for his mom's choice of a new husband, making it clear he loves her and that in spite of his anti-authority attitude he's a Jerk with a Heart of Gold.
• Even the Guys Want Him: Once you gain 100% respect, from all cliques, you can kiss one guy per clique from all the cliques.
• Even Bad Men Love Their Mamas: He doesn't insult his mom in the car ride to school in the introduction, just his new stepdad. He tackles Gary to kick-off the final boss fight, all because of what Gary said, while yelling the loudest and sounding the angriest he's ever been in the whole game.
  Gary: (After listening to Jimmy's Kirk Summation) Well, at least MY mom doesn't make her living on her back!
  Jimmy: YOU'RE DEAD!!! (Tackles Gary right off the roof)
• Everyone Has Standards:
  • He's a brute who has been expelled by 7 different schools but he makes it clear that he's appalled by Bullworth's internal conflict and bullying.
  • Jimmy hates the mistreatment of women, he's disgusted by Earnest's perverse request for pictures of Mandy and angrily says that it's the sort of thing that will land him in prison. When he finds out the Nerds have posted those illicit pictures of Mandy around Bullworth, he's appalled and leaves to go take them down. Internally realising that the Nerds have taken things too far and could have ruined her life through revenge porn.
  • In the fight against Derby Harrington, he's disgusted by Derby's willingness to sacrifice his friends to stop or, at least, weaken Jimmy before they fight each other.
  • When helping Algie confront Lola about toying with his feelings for her, he pats a tearful Algie on the back as a way of saying "I'm sorry you had to find out this way, you'll be ok".
  • As noted in an interview with writer Dan Houser, Jimmy might be a troubled kid but would never grow up to be a violent criminal like other GTA protagonists due to his white-collar background and would instead mellow out with age.
• Expelled from Every Other School: He has been expelled from multiple other schools, and if he gets kicked out of Bullworth Academy he's destined for either Military School or prison.
• Expy: He can be seen as a milder, teenage version of Claude from Grand Theft Auto III, being a rough and tough protagonist who has to fight his way through many antagonistic factions in a town/city in order to stay out of serious trouble after being betrayed by someone close to them.
  • Jimmy also shares some similarities to Tommy Vercetti from Grand Theft Auto: Vice City, as they're both violent characters with a history of getting in trouble with the law, but are loyal, intelligent characters all around who would then take over their respective towns to unify people in need and establish dominance over antagonistic factions after being screwed over by their former friends.
• Extreme Doormat: Jimmy pretty much takes orders from everyone and he'll still go along with them even if he hates the request. He joins in on bullying the homeless man on campus, he helps Earnest get dirty pictures of Mandy, and he begrudgingly helps Johnny Vincent with his girl problems.
• Fiery Redhead: A short, pug-faced ginger kid with strawberry blond hair.
• Former Teen Rebel: According to Dan Houser, if Jimmy were to be portrayed as an adult in the future, he's unlikely to be a criminal and will probably grow up to be a well-adjusted (or at least harmless) individual.
• Freudian Excuse: Jimmy grew up fatherless and his mother is a narcissistic parent who marries men and blames Jimmy for ruining those marriages. Rather than deal with Jimmy's issues, she dumps him at any academy that will take him and make him their problem instead. His gruff and standoffish nature is a result of constantly defending himself from bullies and those out to hurt him.
• Freudian Excuse Is No Excuse: If he gets sent to the principal's office, Crabblesnitch can say that Jimmy's mother issues do not justify his bullying of others.
• From Nobody to Nightmare: By the end of chapter three and start of chapter four.
• Genius Bruiser: Can prove to be a straight-A student, although he still leaves most of his tactical decisions up to Pete.
• Genre Blindness: Mostly when Gary's around.
• Good Is Not Nice: He's stingy with kind words and not particularly philanthropic; he'll protect you from bullies in exchange for cash on the nail. Very rarely does he act out of the goodness of his heart.
• Hard Head: See Made of Iron below, an example of how hardheaded this hard head is would be baseball bats breaking over his skull and he doesn't even blink, and bricks thrown at his head break on contact. That's not possible of a human, let alone a 15 year old kid.
• He Who Fights Monsters: Jimmy originally set out to quash the bullying. However, the popularity goes to his head and he becomes a pale copy of Gary, even inheriting the latter's punching bag, Pete. This comes back to bite him when he ignores Petey and Gary's schemes nearly ruin him, forcing him to become a better person.
• High-School Hustler: A hard-assed incarnation, though you'd need to be to survive in a place like Bullworth. He's also less adept at it than Gary, resorting to fisticuffs rather than flattery and lies.
• Hot-Blooded: Seen as this in cutscenes, but the only time he does impulsively attack in a cutscene, it's when his mom gets insulted by someone who had a beating coming to him anyway.
• Idle Animation: Stands around and talks to himself when left around too long, he wonders how his mom is doing, he decides if school rumors are true or not, he wonders why he's standing around, etc.
• It Runs in the Family: Jim scores with an absurd number of girls throughout the game. It must be in the genes, seeing as how his mother is a serial divorcee.
• Jerk with a Heart of Gold: While willing to do anything for cash and being rude to nearly everyone he interacts with besides the teachers and some of the girls, Jimmy does care about people, going far enough to beat some sense into all the cliques so they could stop bullying weaker kids, and despite being called a psychopath by Pete, he has been shown to have guilt. Principal Crabblesnitch notes that at the end of the game, he is a good person at heart in spite of his rough side, and decides not to send a letter to his mother regarding his expulsion.
• Kavorka Man: While not strictly 'ugly' in any sense, he's not considered to be very good looking—Zoe even makes fun of him for being short and having no fashion sense. But he gets with every hot girl at the school because of his strong personality and natural charisma.
• Kirk Summation: He delivers one to Gary before their final battle.

  Jimmy: Oh, Congratulations! You're smarter than me! You hate everyone and everyone hates you! Genius!

• Knight in Sour Armor: He shows utter disrespect to pretty much everybody, even the principal, but he ultimately does lay everything on the line to safeguard Bullworth. He also shows a softer side to the ladies: When Mandy breaks down at seeing voyeuristic posters of her that the Nerds wallpapered all over the town (with Jimmy's help), Jim tries to console her; then, seeing it did no good, he leaves to deface the posters before the school board sees them.
• Knight Templar: Arguably, he must become the school's biggest bully in order to stop the bullying.
• Kryptonite Factor: invoked Almost nothing fazes Jimmy but chemical warfare. He easily shrugs off physical damage, but reacts badly to stink bombs, fire extinguisher gas, and weed killer. But those are pretty mild compared to the fast-acting sedatives that the asylum orderlies use when busting him. This is expanded upon in a Dummied Out cutscene where if Jimmy loses his fight against Edgar, then Edgar throws him into acid, with his dialogue implying that the acid kills him.
  Edgar: Poor little Jimmy taking an acid bath!
• Lightning Bruiser: He's probably the second or third fastest kid in Bullworth, but he can outrun basically anyone in the game on foot and not run out of breath. For reference, even authority figures (who otherwise have large health bars) will have to stop frequently during chases to catch a breath.
• Made of Iron: Tanks hits from basically a young Andre the Giant, gets up from a sledgehammer swing that sends him flying through boards of wood, takes massive hits from a prized champion boxer, baseball bats break over his head, takes pot shots from a rapid fire potato launcher, gets a nasty Haymaker to the face and drops onto solid concrete, bricks thrown at his head break on contact, gets up from a hard Groin Attack from a musclebound bully, steel pipes dent when it hits him, could survive falling of a long ladder when a wheelbarrow full of cinderblocks thrown at his head, and in the climax, he crashes through multiple boards of wood and falls into a glass skylight, the villain is knocked out from the injury, but Jimmy gets up without staggering, safe to say the visible scars on Jimmy's head must've been from chainsaws because Jimmy is that tough. It's also worth remembering that he's a short 15 year old boy with an average build.
• Married to the Job: Not moments after professing love for Zoe, he turns on his heels and races back to Bullworth upon hearing it's in trouble. "Duty calls!"
• Martial Pacifist: Downplayed as his favorite solutions are violence, but he's willing to do tasks for people if it means it won't cause more hostility and problems. He steals bikes for Clint/Henry so he won't fight Jimmy, and he finds who stole the Preps' boxing trophies if it means that they won't fight the Greasers again.
• Mistaken for Gay: Pinky mentions rumors that Jimmy is confused about his sexuality, which Jimmy takes offense at. However there are several boys that Jimmy can kiss for a health bonus just like with the girls meaning he is bisexual, and is either uncomfortable talking about it or took offense to the insult behind the rumor. Lola also accuses him of liking boys due to his lack of interest in her.
• Motive Decay: At first, he's only fighting off other people because they leave him no choice and it's the only way he can get them to stop bothering him. Eventually, he becomes determined to keep the sadistic kids of Bullworth in line, including Gary, by beating them up and forcing them to unite under his watch. Then, when he topples every school clique, he simply lives the high life of popularity and forgets about Gary. He reverts to the second plan when things go south and he seeks to set things right.
• Mouthy Kid: His snark tends to lands him in trouble. He almost gets thrashed by Johnny Vincent on the spot for a comment, his cute little one liner gets turned into a Pre-Asskicking One-Liner by Norton, and his words make Headmaster Crabblesnitch hate him more.
• Muscles Are Meaningless: Despite not appearing very muscular, Jimmy can hold his own in a fight against opponents bigger than he is... including the gigantic Russell.
• The Napoleon: He's short for his age, which is one of the very many things responsible for his general belligerence.
• Nice, Mean, and In-Between: He's the In-Between to Pete's Nice and Gary's Mean. Jimmy is a violent, cynical Anti-Hero who usually asks, "What's in it for me?" before helping others, but he cares about others more than he'd like to admit and only beats up people whom he thinks deserves it.
• Not Afraid to Die: Jimmy never shows any signs of fear throughout the game, even when faced against the strongest person in town, a maniac with a sledgehammer, an army of highly intelligent Nerds equipped with explosives and a rapid-fire potato gun, or a homicidal sociopath on the roof of the school.
• Not So Above It All: While he hates bullying, and he fights to stop it, he seems to enjoy bullying and humiliating people when they're low on health; giving wedgies, pinching girl's asses, giving swirlies and threatening people. The only difference between his bullying and the students of Bullworth's bullying is that Jimmy only targets people who have done something to deserve it in the story, while the students enjoy bullying anyone weaker than them.
• Odd Friendship:
  • Despite Pete typically being the type of boy that the students at Bullworth Academy would target and often not treating him well himself, Jimmy is friends with him regardless. At the end of the game he decides that he would be an excellent choice for the head boy.
  • He thought he had this with the Nerds since he's been helping them since the start of the game, but when he came to them for help taking down the Jocks they showed how one sided this friendship was which forced him to fight them like with the other cliques.
• One-Man Army: Throughout the course of the story, he manages to beat up a man twice his size in Russell, as well as trained boxers (sometimes several at the same time), the entire football team, a well-armed militia of nerds wielding potato guns and firecrackers, a violent Scary Black Man attacking him with a sledgehammer, and a psycho wielding a steel pipe, all by himself. Safe to say it would take a freight train to stop Jimmy Hopkins.
• Only Sane Man: Well, he, Pete, and Zoe share this. Still, Jimmy deserves special mention, as his scathing sarcasm at everybody else's insanity/stupidity flies completely over their heads.
• Parental Neglect: His father is out of the picture and his mom is too busy dating to give Jimmy any attention. Jimmy had to learn how to fight and defend himself in response. Due to Jimmy's behaviour, he frequently gets expelled and he is eventually sent to Bullworth.
• Pet the Dog:
  • When Algie sees Lola cheat on him with Chad and starts tearing up, Jimmy comforts him by patting poor Algie on the back.
• Pint-Sized Powerhouse: His height is no disadvantage to him in a fight. Jimmy can take on a whole clique in a fist fight single-handed and win.
• Pipe Pain: In the secod phase of the boss fight against Edgar, he also rips off a large pipe and uses it to give Edgar a taste of his own medicine.
• Pride Before a Fall:
  • It's even part of the last story-based chapter: "The Fall and Rise of Jimmy Hopkins, Aged 15". It is also a reference to the 1970s book, The Fall and Rise of Jimmy Hoffa, by Walter Sheridan.
• "The Reason You Suck" Speech: Gives one to Dr. Crabblesnitch before he gets expelled, outlining everything wrong with the school while insulting him.
  Jimmy: I'm not the one who's funny. You know what's funny? You! You're a joke, you old creep! You and your stuck-up, lame-ass school, with its bullies and sex-pest teachers. This place is a dump and you're a big-nosed freak! This school rewards losers and bullies, I just stand up to them!
• Sociopathic Hero: Commented on primarily by Pete, it isn't obvious until Jimmy mistakes a request to kill a houseplant with killing Derby instead. And though his tone of voice makes it unlikely that he was going to actually do it, he doesn't even question the request until he's corrected.
• Stock '90s Bad Boy: Jimmy is a 15-year-old high schooler who got expelled from at least 7 schools and has to attend Bullworth Academy as his last chance for a better life. He has blond hair, has an enemy in a Dean Bitterman, carries a slingshot, rides a bike and a skateboard, is fairly Book Dumb and has a disdain for authority.
• The Stoic: He rarely smiles, and even at his angriest, his voice is rather muted. However, he acts like a Boisterous Bruiser Large Ham once he's done kicking someone's ass, besides that, only Gary manages to get a rise out of him.
• Tiny Guy, Huge Girl: Jimmy cobbles together his own little harem as the game progresses. It helps that every teenage girl in school is a Statuesque Stunner, towering over all the non-Prefects with the exception of Eunice, and even she has an inch or two on Jimmy.
• Tiny Schoolboy: The third shortest student in the entire school, just ahead of Pete and the little kids.
• Trademark Favorite Food: Soda, and it's the only consumable that Jimmy comments on (he never says anything when eating apples or bananas). Jimmy even knows it's unhealthy for him but drinks it anyway. The game also encourages the player to chug them, with rewards given for buying 100 and 500 sodas. All his save zones have soda machines in them too, and the nerd hangout has always has a lone soda consumable for Jimmy to drink near his bed. He even steals soda off people he knocks out, the only other thing he steals off people is small weapons.
• Unwitting Pawn: Gary builds him up as the school hero, only to muddy his reputation in the penultimate chapter. Then Jimmy rebuilds his reputation by doing good deeds like putting out a gym fire, and rescuing mostly innocent men/boys from an asylum. When it still doesn't work, Jimmy just does it the old fashioned way and beat everyone, including Gary, back into knowing who's boss.
• Upbringing Makes the Hero: According to Dan Houser, the fact that he comes from a mostly white-collar background and was able to afford going to a private school means that by Rockstar Games standards he has a relatively fortunate upbringing and would probably not become a violent criminal as an adult.
• Virtual Paperdoll: Jimmy is definitely one of the most customizable Rockstar protagonists. You can dress him fancily, casually, like a clique member, put on a wacky costume that'll get him laughed at, abide by the school's dress code, or simply give him your own style. And that's not even mentioning the hairstyles and tattoos available for him.
• Wise Beyond His Years: Due to his father abandoning him and his mother neglecting him, Jimmy is more mature than the other students and more capable of defending himself.
• Working-Class Hero: Jimmy shows traits of an apolitical Skinhead, that being he's got a buzzcut and comes from a working-class family. Jimmy had to look after himself after his father abandoned him and rebellious behaviour has gotten him expelled from several schools.

Voiced by: Peter Vack

• Abusive Parents: You can get an image of Gary's home life by piecing together bits of gossip, and it doesn't sound like he has a good one. Mr. Smith, the super-rich self-made man who can be seen in Bullworth Town, is thought to be Gary's grandfather. Gary's father did not turn out well, and ended up in an unhappy marriage with a woman of a seedy background from New Coventry. And poor Gary got dumped at Bullworth as soon as he was old enough.
• Ambitious, but Lazy: Gary wants to take over the school, but his idea is to trick Jimmy into doing it for him. Gary's plan to take over merely surmounts to "Get everyone to fight each other, and then fight the last one standing". This fails because Gary has no fighting experience and relies on his final opponent being too injured and exhausted to fight effectively. Although Jimmy might have been injured by the time he confronts Gary in the bell tower, he's still a skilled, experienced opponent fighting a guy who's one ability is to rile people up.
• Ax-Crazy: A sadistic, dangerous, murderous, delusional and power-hungry paranoiac with an unidentified mental illness that he actively stopped taking medication for. Even Jimmy calls him a psycho.
• Bad Samaritan: He's the first person at Bullworth to act friendly to Hopkins (if condescending but that's the Bullworth's friendliness), so naturally, he's the root of its evil.
• Believing Their Own Lies: He's somehow convinced himself that Jimmy has been speaking badly of him and plans to take over the school, something Jimmy repeatedly denies and confused by.
• Between My Legs: When Jimmy finally confronts him on the roof, the camera switches to this view.
• Big Bad: The ultimate bully in Jimmy's eyes as Gary manipulates everyone from Jimmy, to the principal, to even all the clique leaders throughout the entire game. Also the final enemy Jimmy must beat if he wants to save the school.
• Bitch in Sheep's Clothing: Gary acts friendly and helpful whenever authority figures are around. As soon as they're gone, he drops the act and reveals himself to be a cruel, selfish manipulator.
• Blessed with Suck: Gary views his own intelligence as this. Although he's diagnosed with ADD, this is another classic symptom of sociopathy: proneness to boredom and obsessive need for stimulation.
• Boisterous Weakling: He can gloat big, but when it comes to physical combat, he's dropped in a matter of seconds, as shown in the final altercation between him and Jimmy, as he only gets the upper hand when throwing objects at Jimmy.
• Brains and Brawn: Brains to Jimmy's Brawn. He was later replaced by Pete.
• Bullying a Dragon: In an early mission, he thinks it's a good idea to bully a nearby hobo by the gates seeing him as an easy target. Unsurprisingly, the hobo (who happens to be a war veteran) easily scares him (and Pete) away easily.
• Chronic Backstabbing Disorder: Gary's paranoia is so all-encompassing that he can't help but betray people.
• Comic-Book Fantasy Casting: Resembles Christian Bale as his character from Swing Kids (especially when wearing a Nazi uniform).
• Corrupted Character Copy: Gary appears to be a corrupted version of Ferris Bueller from Ferris Bueller's Day Off, as both have similar face shapes, brown hair, and both are known to be the leader of their friend groups. While Ferris was at least well-intentioned, only manipulated others so he can have fun with his friends, stands up for the little guy, and only targeted people who did something to him to deserve it, Gary is what happens when you take away Ferris's sense of loyalty to his friends and focused solely on Cameron Frye and Edward R. Rooney's side of the story. Gary is shown from the start to be mean to his friends, bullies Pete for being one of the weaker kids, and his idea of fun is dragging his friends away to bully the homeless man on campus for being helpless and unfortunate. He does this after being offended by the notion of being called boring and he bullies Algie after convincing Jimmy to help him save Bucky from the bullies in order to send a message to Russell and his boys. When Jimmy tries to convince him to dial back their trouble-making so they don't get expelled, Gary becomes offended and drags him to The Hole so Russell can beat him up in a staged fight in front of the other cliques. Throughout the game, Gary poses as an ally of the clique and stirs up trouble for Jimmy to fix and he succeeds in getting Jimmy expelled and turning all the cliques against him. Once Jimmy is away, Gary manages to turn all the cliques against each other, take over the school, and tie up the headmaster. When demanded to know why Gary betrayed him so many months ago, Gary simply says that he enjoys that feeling of power, likes manipulating others, and enjoys getting a reaction out of people. The game ultimately shows that these sorts of characters would be psychopaths in real life if they had this level of charisma.
• Deadpan Snarker: Many of his remarks towards different characters and about society as a whole are usually condescending and cynical.
• Deal with the Devil: Gary makes the same sales pitch to everybody when tempting them to the dark sid— er, his clique. First he promises to divide Bullworth between them 50-50, then pretends to assume a strictly advisory role. Earnest is especially susceptible thanks to his own naked lust for power and messiah complex.
• Deconstructed Character Archetype: Gary Smith is a deconstruction of the High-School Hustler and the Delinquents. Gary is introduced as Jimmy's first friend in Bullworth because everyone needs one to survive the academy and Jimmy only joins him because Gary was the first student who didn't try to beat him up in the first meeting. In chapter one, he leads Jimmy and Petey on all sorts of antics in school but these aren't played as awesome and funny; Gary shows himself as a callous bully who makes fun of the homeless, bullies Petey, and gets his friends in trouble for kicks. When Jimmy repeatedly tells him to calm down and stop before he gets them both expelled, Gary is offended and drags Jimmy to the hole and pits him against Russell under the erroneous belief that Jimmy hates him and will betray him. His goal to take over the school was interpreted as "let's be the most popular kids in school." when he actually meant "Let's do a hostile takeover of the school and get everyone to fight each other". By the final chapter, Gary has not only lied his way to the top; he turned all the cliques against Jimmy, got the teachers and prefects on his side, and got Jimmy expelled. Gary shows how much a sociopath he is by revealing how much he enjoys manipulating people, and how he got other kids in the past unfairly expelled and put others in therapy because of his actions. In summary, this game shows how a High-School Hustler can't exist in the real world without being a power-hungry manipulator, how sociopathic and inattentive delinquents actually are, and how you shouldn't befriend people simply because they fit the bare minimum of basic decency.
• Devil in Plain Sight: If the comically-large scar over his eye, bouts of psychosis, and thinly-veiled contempt for all around him wasn't enough, he dressed up as an S.S. Officer (complete with a baton) for Halloween!
• Diabolical Mastermind: As shadow leader of the various cliques. The Nerds, Jocks, and Greasers are made to wage war on each other, not realizing their orders all came from the same place.
• Diabolus ex Nihilo: There is no in-game explanation as to why he's so sociopathic and power-hungry, he simply wants to control the school and take over.
• Dirty Coward: Gary spends the first half of the "Final Confrontation" running away from Jimmy, attempting to throw bricks at Jimmy, and drop construction equipment on him as Jimmy climbs a ladder, all the while gloating about how he outsmarted Jimmy and how easy and fun it is to manipulate people. In the first chapter of the game, Gary is shown bullying Algie and Petey, archetypal victims of bullying in Bullworth and they are both shown to be weak and unpopular in the academy. When we see him fight (until the final chapter), Gary is shown to have a similar fighting style to the Bullies, ultimately showing that Gary is simply a braggart who can't fight his own battles and has to rely on others to either back him up or fight for him by tricking them into doing so. It's also worth noting that he tells Jimmy to avoid the Jocks and chooses to sit and watch as Jimmy uses a slingshot on them from a tree, showing that he recognizes them as a threat.
• Disney Villain Death: Not really, but Hopkins does shove him off the school roof and into the skylight above Crabblesnitch's office. This knocks him out cold.
• Dog-Kicking Excuse: Gary just enjoys hurting and manipulating other people; he does jokingly mention several other issues he has, and it's even said that he's off his medication, but ultimately, he just does what he does for the sake of doing it.
• Drug-Crazed Savagery: Inverted. One of the reasons why Gary betrays Jimmy is that he stopped taking his medication, causing him to become more violent and paranoid, insisting that Jimmy wanted to take over Bullworth Academy and would betray Gary to do so.
• Engineered Public Confession: Jimmy doesn't even plan it that way; Gary can't stop running his fool mouth off about how he fooled everybody. Crabblesnitch overhears his evil rant and expels him.
• Establishing Character Moment: When Jimmy meets Gary, he tries schmoozing the new kid with Faux Affable small talk. When it fails to endear Jimmy immediately, he talks to Jimmy as though the school is a prison where being hostile to everyone won't get him anywhere and that he needs to start making friends before they start putting him on medication. This establishes him as the manipulative-type who views companionship as entirely transactional. He also mentions that he was forced to take medication after his behavior became too bad for the staff to ignore, Foreshadowing his Face–Heel Turn when he stops taking them later.
• Evil Cannot Comprehend Good: He clearly can't wrap his mind around the concept of 'friendship,' and the idea of sharing power is equally anathema to him.
• Evil Counterpart: Pretty much serves as one to Jimmy. Its implied that, just like the former, he had Abusive Parents. Also both have a knack for leadership when it comes to trying to rule the school. However while Jimmy is generally a Nice Guy underneath a tough exterior and only takes over the school to ensure peace and harmony, Gary only cares about himself and uses manipulation on others to gain power for himself.
• Evil Is Hammy: "Face it: I'M SMARTER THAN YOU! HA HAAAAAHH!!"
• Exact Words: When he told Jimmy that he had plans to take over the school, he didn't mean becoming the most popular student. He literally meant to take over the school through a hostile takeover.
• Exposition Fairy: Gary acts as one in "This is Your School".
• False Friend: To both Jimmy and Pete, as Jimmy is just another pawn to him and Pete is just his punching bag.
• Fatal Flaw: Pride. The smug bastard just can't stop bragging, and he takes genuine offense when Jimmy calls him "boring."
• Faux Affably Evil: He's on his best behavior when adults are watching, and acts friendly to students he's trying to manipulate, but it's plainly obvious that he's faking it.
• Final Boss: He's the last boss fought in the game.
• Fisher King: When he takes over the school, a storm forms over the campus, and it disappears once Jimmy emerges victorious from the fight.
• Flat Character: Despite being the main villain of the game, he only appears in cutscenes where he brags about his plans, stating how he hates Western society and talking to other students to cause problems for Jimmy. There's no explanation for his character or an explanation for why he wants to take over except his ego and sociopathy.
• For the Evulz: Gary represents abuse of power for its own sake, making him the ultimate bully in Jimmy's eyes.
• Freudian Excuse:
  • During the final mission of the first chapter, he excitedly stated that he stopped taking his meds. His behavior implies that he may also suffer from schizophrenia.
  • Some dialogue also indicates Gary's father wound up going to prison, which likely meant he didn't come from a well-adjusted home either.
  • Parodied by himself, where he casually lists off all his potential excuses, each more ridiculous than the last, in a cheery tone people would use to rattle off academic credentials, when Jimmy asks him "What's your problem?"
  Gary: Well – A.D.D., primarily, but also life, my parents, this school, western civilization, but really, honestly, enough about me…
• Friendship-Hating Antagonist: His throw away idle line (heard by clicking at his soundboard, or by modding him to appear in free-roam) makes it clear that he despises the idea of friendship. He is not kidding about it.
  Friends? Friends are for the weak!
• "Get Back Here!" Boss: In the last confrontation, Gary leads you up the dilapidated bell tower, hoping you'll slip and fall. He fires some taunts and turns over wheelbarrows full of cement blocks from above.
• Good Hair, Evil Hair: Gary has a unique hairstyle through a side-swept undercut. Undercuts were popular from 1910 - 1940, while they were initially associated with poverty and the inability to afford a barber who could properly blend in the sides, it was eventually associated with The Third Reich after undercuts became one of the mandatory hairstyles for German soldiers. In the game, Gary is the main antagonist and while it's never outright said that Gary is a supporter of Nazism, he doesn't care about dressing like one and it appears that he's doing it for shock value than anything else.
• Hate Sink: There is nothing remotely likeable about this manipulative and sociopathic bastard.
• Heel Realization: Kinda.
  Jimmy: You are sad, man.
  Gary: I may be sad, but I run your world, moron! And don't you forget it!
• High-School Hustler: Deconstruction of the Ferris Bueller archetype, expertly manipulating students and staff for his personal gain. As Bully demonstrates, only a psychopath would be this good at it.
• Hypocrite:
  • He forces Jimmy to be his own personal Puppet King of the school, only to then betray him for being "competition" in his bid to take over the school. He also accuses Jimmy of lying about him behind his back, but all he ever does is trying to pit Jimmy against everyone else (both before and after his betrayal) with one baseless accusation after another. Considering he's mentally ill and had then stopped taking his meds, he might genuinely believe his own Insane Troll Logic.
  • He calls Lola a whore for using her charm to manipulate several people into fighting each other, so she could satisfy her ego. He himself does the same thing in an even bigger scale.
• Hypocrite Has a Point: Although a sneaky and manipulative bastard in his own right, he was right in the end that Jimmy should be wary of the Nerds as they were shown to be sneaky, vengeful, and unscrupulous in their rivalry against the jocks.
• Idiot Ball: Inverted. Gary seems to be immune to the effects of an Idiot Ball, but he carries a very powerful one at all times. It's the most reasonable explanation as to why everyone seems to lose half of their IQ whenever Gary talks to them. People who previously talked about how he was an unstable psychopath are always willing to take him at his exact word, and Jimmy never seems to think of just beating him up until he is at the absolute peak of his power and causes Jimmy genuine trouble.
• Improperly Paranoid: His Chronic Backstabbing Disorder is fueled by him being absolutely convinced everyone wants to rule the school in spite of Jimmy clearly not seeing the point of "ruling the school" and vocally so. Eventually, Jimmy develops an ambition to take over the school purely to get Gary off his back.
• Informed Flaw: Gary is supposed to be the most hated student in Bullworth but yet, whenever Gary makes some sort of lies and manipulations, they immediately listen to him over the reliable Jimmy Hopkins with Crabblesnitch even lauding him as one of the ideal students for the head.
• Insane Troll Logic: He basically drags Jimmy kicking and screaming into his plotting to take over the school, despite the fact Jimmy doesn't care about ruling the school (at first, anyways) and tells him that repeatedly, and he only helps Gary because he's one of the only students at Bullworth who doesn't treat him like dirt. Later, Gary betrays Jimmy because he's "competition," which comes out of nowhere from Jimmy's point of view.
• Insufferable Genius: He's the egotistical douchebag that loves to brag his intelligence.
• It Amused Me: When Jimmy asks, "Why'd you do it?", this is his response. The fact that Gary took the Principal hostage and turned the school into a warzone, yet is still Head Boy makes his victory all the sweeter; in Gary's mind, he's proven his superiority over the "little people."
• Jerkass: He's a selfish, arrogant, manipulative and sociopathic narcissist that gets on everyone's nerves.
• Jerk with a Heart of Jerk: Gary comes off like a immature braggart in Chapter 1, forming his own clique with Jim and Pete while simultaneously claiming that friendship is just illusory. It later turns out Gary isn't hypocritical or putting up a tough exterior: he really is that evil.
• Kick the Dog: Callously tells Jimmy that they were never actually friends and tells him how worthless he thinks he actually is.
• Knight of Cerebus: The plot becomes progressively darker and more dramatic whenever he is carrying out some of his most despicable plans.
• Laser-Guided Karma: After being expelled in place of Jimmy, NPC chatter reports that he's skulking the belltower like the Hunchback of Notre Dame (though this is probably an exaggeration) and—more likely—living in the trailer park with the Townies.
• Let No Crisis Go to Waste: Once Jimmy becomes Bullworth's King, Gary ratchets up the chaos by letting rats loose in the library, destroying the Preps' antique trophies, getting Johnny sent to the asylum, and setting the gym on fire. This ends up turning all the cliques against Jimmy and allows Gary to become king of school instead.
• Let's You and Him Fight: Gary couldn't conquer the cliques with his fists, and needed a brute like Jimmy to lead them. Once Jimmy becomes the King of School, Gary undoes the efforts he took to improve Bullsworth Academy and arranges for his expulsion, leaving the leaderless and confused gangs in need of a hand: Gary Smith's.
• Loners Are Freaks: There's a reason we rarely see Gary following the fight in the sewers: He spends nearly all his waking moments in the dormitory, making plans. In doing so, however, he missed out on all the action Jimmy was having around town; adventures that, in theory, Gary could have participated in, instead.
  While you were off wasting your time with whores like Lola, I was in the dorm, planning. While you were racing bikes, while you were playing at the carnival like a child, my plan was coming together!
• Manipulative Bastard: Gary is a devious narcissist with a superiority complex and he is completely devoid of morals, doing whatever he deems necessary to achieve his goals, which includes manipulating teachers and social cliques into fighting each other.
• Mirror Boss: Heavily downplayed, all things considered, but his fighting style during your final encounter with him does in fact take noticeable cues from Jimmy's own moveset though with a few tweaks here and there. His front kick and his ducking jab are dead ringers for a couple moves Jimmy learns from the hobo and his combos visually look similar to Jimmy's own wide-swinging jabs, hooks and uppercuts. It also helps that he's about Jimmy's heights and your attacks will be knocking him about about as much as his do you, provided you actually let him land attacks on you.
• Misanthrope Supreme: Among his pet, the people he hates are his parents, his school, "small" people, and western civilization.
• Mission Control Is Off Its Meds: Gary was introduced as Jimmy's first friend at Bullworth and he's the one who gets Jimmy into all sorts of antics. By the final mission of chapter one, Gary admits to being off his medication and orchestrates a fight between Jimmy and Russell under the belief that Jimmy is threat to him.
• Motive Rant: An extended one in the finale, which proves his undoing because it enrages Jimmy enough to beat him, and then the principal sees his true colors by hearing the rant and expels him.
• Narcissist: Thinks he's smarter than everyone else and sees himself as unstoppable as he manipulates everyone into doing his dirty work for him and has no remorse towards the suffering he causes as long as it benefits him.
• A Nazi by Any Other Name: As his Halloween costume suggests, Gary is a non-too-subtle parody of Adolf Hitler (right down to the haircut). A hysteric xenophobe, possibly suffering from some form of parental neglect or mental illness, who comes to power by way of a series of extralegal maneuverings, sets fire to Bullworth's gym in his very own riff on the Reichstag, and talks constantly of ruling his own evil imperium someday.
• Near-Villain Victory: He does succeed in taking over the school and gets Jimmy expelled, but he didn't expect Jimmy to form an alliance with the Townies or care enough to retake the school and have revenge.
• Nice, Mean, and In-Between: He is the Mean to Pete's Nice and Jimmy's In-Between. Gary is a cruel, arrogant, manipulative asshole who can't go 5 seconds without insulting someone and loves creating chaos for its own sake.
• Non-Action Big Bad: He's a whiz at manipulation and backstabbing, but a in a straight fistfight his bark proves to a lot bigger than his bite.
• Not-So-Harmless Villain: Somehow, he was apparently able to convince all of the cliques to trust him, although most, if not all of their leaders show open disdain for Gary. He also does temporarily take over the school and get Jimmy expelled.
• Obviously Evil: He bullies Petey in front of Jimmy, leads the trio in causing trouble, verbally abuses his friends, dressed as a Nazi for Halloween, openly talks about a big plan, and he has a scar on his face with an SS haircut. The only way he'd more obvious as a villain would be if he had the words "Definitely won't stab you in the back" emblazoned on his sweater vest. Granted, this may have been a result of his ADHD since he's too excited about his plans to control himself and he's deliberately refusing to take his medication.
• Offstage Villainy: Most, if not all of his actions and manipulations are done offscreen although this is justified as the game is mostly done from Jimmy's point of view, and Gary admits he was planning from the shadows.
• Psychological Projection: Throughout the whole game, we see Gary constantly pitting people against each other for kicks and putting words in other people's mouths to gaslight them, so it comes off as hypocritical when he baselessly accuses Jimmy of saying things behind his back and using this as a reason to backstab him.
• "The Reason You Suck" Speech: He delivers quite the massive one in the final mission. It's arguably one of the most famous speeches in the game.
  Gary: You're too trusting, Jimmy. From the start you were pathetically naive... Poor little Jimmy, all alone at big scary Bullworth. Under fire from Russell and his goons, desperate for help. So sad, so hopeless, just needing a friend. Any friend. You were so easy to manipulate, Jimmy! And once we were friends, it was all so clear. You had your lust for power, but without the intelligence to back it up. Using you as a pawn was so wonderfully obvious! Let Jimmy have his fun. Let him play his childish little games with Earnest, Ted, Derby, Johnny and Edgar, and just wait for the right moment to swoop in and take it all. It was like lining up dominoes. It all fell together so perfectly. While you were off wasting your time with whores like Lola, I was in the dorm, planning. While you were racing bikes, while you were playing at the carnival like a child, my plan was coming together... Any regrets, Jimmy? Looking forward to the wasteland that your life is about to become? After you're expelled for your antics over the last few weeks you won't have anywhere left to go!
• Red Eyes, Take Warning: His brown eyes border on the color of being red, which is fitting, considering his status as the main villain.
• Sadist: Loves to see people suffer for his own amusement, Jimmy himself even states to Crabblesnitch that Gary loves to torture people.
• Sanity Slippage: Becomes more excitable (and erratic) after going off his meds. "I should've gone off those pills a long time ago!"
• Self-Fulfilling Prophecy: Jimmy eventually does take over the school before him, just as he suspected — which wouldn't have happened if Gary hadn't accused Jimmy of trying to take over.
• Smug Snake: Gary's general tone of voice could best be described as "seething contempt." He's the "would-be genius Chessmaster but too arrogant to pull it off" version of a Smug Snake—although he does manage to become the Big Bad he's utterly incapable of maintaining it.
• The Social Darwinist: Frequently proclaims his contempt for "weak people" and the necessity of betraying your friends first. He's also under the delusion that everybody in the world thinks just like him, including Jimmy.
• The Sociopath: Textbook case. He's also unable to grasp the difference between holding total power over others and real friendship. He's actually called a sociopath in-game, but Jimmy doesn't know what that means.
• Stupid Evil: His ultimate plan to take over the school results in a mass riot, the teachers abandoning the school and the headmaster being knocked out and tied up. Gary's plan would never last; the police will eventually break down the gates and restore order, Crabblesnitch would figure out who knocked him out, and the cliques would eventually wise up to his behaviour and punish him for pitting them against each other.
• Take Over the City: Take Over the School — His goal all along was to become head of the school, with each of the cliques answering to him.
• They Look Just Like Everyone Else!: His bad temper went mostly unnoticed on the dog-eat-dog campus.
• Toxic Friend Influence: Gary is the grand orchestrator of the cliques, he poses as their friend and spreads lies about Jimmy to get the cliques to fight him for Gary's amusement.
• Vile Villain, Saccharine Show: In a world that wouldn't be out of place in a Slice of Life or Teen Drama, Gary Smith stands out as a particularly sadistic, sociopathic, and manipulative young man. He's essentially the dangerous psychopath or mobster in his teenage years. It's telling that even the other students know he's a sociopath, so they go to great lengths to avoid any form of association or interaction with him.
• Villain Cred: Gary Smith is renowned in the cliques for his sadism, though Jimmy doesn't quite believe it.
• Villain with Good Publicity: Crabblesnitch lauds him as a role model who isn't afraid of being an "unpopular leader." Doubtless this was his interpretation of why the cliques all loathe Smith, yet seemingly follow him without question.
• Was It Really Worth It?: Jimmy delivers this to him after he took over Bullworth Academy and turned it into a chaotic hellhole.
  Jimmy: Oh, congratulations. You're "smarter than me"! You hate everyone and everyone hates you! Genius!
• We Win, Because You Didn't: Gary gloats about this in "Complete Mayhem", explaining that if Jimmy loses against him, he's just another bitch — but if the Head Boy is beaten up, Jimmy will be in even worse trouble. This winds up being moot when the Headmaster overhears his entire speech.
• Wrong Genre Savvy: Gary sees himself as some sort of master manipulator, who has the ability to read people like books and can easily manipulate them without effort. In actuality, Gary's silver tongue is simply knowing what buttons to press and where to direct the target. His "charm" consists of backbiting and sucking up to Crabblesnitch while everyone is busy fighting. In chapter 1, his medication kept him calm and level-headed but as soon as he's off them. He's barely restraining himself when he says he has big plans to take over Bullworth. His end goal makes no sense; have all the cliques fight each other, tie up Crabblesnitch, and lock everyone else out of school while he just watches the fight from inside. The only reason he gets kicked out in the first place is that Crabblesnitch heard him loudly gloating from the bell tower.
• Your Mom: The last mistake he makes before Jimmy kicks his ass is insulting Jimmy's mother.

Voiced by: Matt Bush

The less action-oriented of the trio, he's a smart but quiet boy who puts Jimmy's aggression to their advantage.

• Almighty Janitor: As a social outcast, Pete is often ignored or avoided by the other cliques, however, Pete is considerably smart, possibly even rivalling Gary. His advice to Jimmy was valuable in his campaign against the Preps and the Nerds, and he also zeroed in on Gary being the one plotting behind their backs.
• Ambiguously Gay: Petey is suggested to be either bisexual or gay because of his shyness and lack of friends, not to mention an excruciatingly awkward joke he makes suggesting that Jimmy would make a good male stripper. He's also a fan of Bullworth's televised swim practice sessions, which feature both male and female participants.
• Animal Motif: Downplayed, he dresses like a rabbit for Halloween and matches the stereotypes rabbits have. Rabbits are prey animals in the unforgiving wild, and Petey is the archetypal victim of Bullworth as he's seen as small and weak by the other kids, which makes him vulnerable to bullying without Jimmy to protect him. Rabbits are often portrayed as intelligent tricksters who survive by outwitting stronger opponents. Petey is a cunning strategist who helps Jimmy take on the other cliques and uses a magnet to weaken Johnny Vincent.
• Beneath Notice: He's largely ignored by the other cliques due to his social awkwardness and lack of fighting skills. Even Headmaster Crabblsnitch outright admits he hasn't heard of him.
• Beware the Nice Ones: Petey is a shy person who has trouble making friends but he's also the nicest of the main characters and extremely cunning as he's able to figure out how to beat the Nerds and the Preps.
• Big Damn Heroes: He appears in the junkyard and activates the magnet that gets Johnny Vincent off his bike, allowing Jimmy to beat him and take over the Greasers.
• Bully Magnet: He's a target to practically everyone.
• Butt-Monkey: Mocked by nerds, stuffed in a garbage can on Halloween night, and receiving no end of torment from his supposed 'friends'. He later admits he put up with Gary and Jimmy's abuse because it was better than the alternative.
• Color Motifs: Pink, as shown by his pink shirt and pink bunny suit on Halloween, reflecting his social ineptitude and perceived weirdness.
• The Consigliere: Jimmy solves his problems with violence, but he sometimes needs Pete to tell him where to direct that violence. It is best demonstrated when Pete advises Jimmy to take on Bif Taylor in a boxing match to subdue the Preppies.
• Custom Uniform: Wears the same blue and gold Bullworth vest that Jimmy has, and wears a pink shirt underneath^note (although from the washed out pink color, it might have been a white shirt that got cleaned up with something colored red
• Embarrassing Nickname: He really doesn't care for being called Petey, although he's too meek to do anything about it.
• Extreme Doormat: He's extremely meek pushover that lets Gary, Jimmy and anyone else walk all over him do what they want.
• Foil: His shy and cautious personality contrasts with both Jimmy and Gary, who are a school bully and a sociopath respectively. As such, he's considered to be a better candidate for head boy.
• Groin Attack: Falls victim to this in "Slingshot".
  Gary: Don't lie, Petey. Don't you lie. Because you know what happens to liars?
  Petey: No, no. I'm not lying.
  Gary: We kick them in the balls. *kicks Petey in the groin*
• I Just Want to Have Friends: Laments this to Jimmy after Gary goes off his rocker. His friends might have been a "snake" and a "psychopath", but he liked having a little clique of his own.
• The Lancer: The Non-Action Guy with a strong moral center and aversion to violence to Jimmy's easily-influenced Blood Knight Anti-Hero. He's one of Jimmy's few real allies to never abandon him.
• Loners Are Freaks: Analyzed trope, in contrast to genuinely antisocial Gary Smith. Pete's solitude is taken as proof by the cliques that something's wrong with him.
• Mistaken for Gay: Because of his pink shirt, lack of social skills, and avoidance of fighting, his masculinity is constantly mocked by Gary.
• Morality Pet: To Jimmy. Though he treats him like a tag-along kid, he still protects him more than any other character. Might be because, to Jimmy, Pete represents the ultimate "helpless bullying victim".
• Mundane Solution: After explaining how Jimmy previously tried to fight the preppies, Pete is the one who tells him to beat up Bif Taylor in a boxing match. He also directs Jimmy to Earnest when he fails to reason with Algie.
• Nerdy Inhaler: One of his chatters mentions he might have a breathing problem.
  "Oh man, I gotta get checked out for my asthma..."
• Nice, Mean, and In-Between: He is the Nice to Gary's Mean and Jimmy's In-Between. He's a polite, sensitive Extreme Doormat who often tries to stay out of trouble.
• Non-Action Guy: The closest he comes to doing something action-y was during the boss fight against Johnny Vincent, where he operates an electromagnetic crane... after Jimmy knocks out every single Greaser who was in his way.
• No-Respect Guy: Not even Jimmy, who is his only real friend, shows him much respect at all. At the very least, he does get to be the Head Boy at the end of the game.
• Odd Friendship: Though he's typically the type of boy that a bully would target, he and Jimmy are rather good friends. Gary, in contrast, is a False Friend.
• Only Sane Man: He continually tries to warn Jimmy about imminent dangers, but Jimmy neglects him more and more as his popularity increases.
• Pink Is for Sissies: He also wears a pink bunny suit on Halloween, but only after being forced into it by Gary. Also, his Bullworth shirt appears to have been dyed in the wash.
• Pint-Sized Powerhouse: Not nearly to the extent of Jimmy but during the few times he shows up as an NPC (or when spawning him with PC mods), he can hold his own against bullies like Trent and will regularly beat up nerds in a straight fight despite the height difference.
• Sensitive Guy and Manly Man: Pete plays the sensitive guy to both Gary and Jimmy's manly men.
• Throw the Dog a Bone: The Headmaster appointed him Head Boy offscreen.
• Tiny Schoolboy: The shortest teen character in the game, as he's even shorter than Jimmy and barely taller than the Little Kids! It really doesn't help him in a place like Bullworth. Gary, of course, lampshades it by mockingly suggesting that he's only just now hitting puberty.
• You, Get Me Coffee: Pete almost never accompanies you into a mission, despite repeatedly asking. He does turn up unannounced in a few missions, and proves handy during the Johnny Vincent battle.

• All the Other Reindeer: They are the students who are not affiliated with any of the cliques, either because they were too young, ineligible, or otherwise. They are bullied by everyone, even by the Nerds.
• Color Motif: They all wear dark green.
• Hufflepuff House: Other than Constantinos, they don't appear in the main story and are largely ignored by Jimmy.
• Hypocrite: Angie and Christy can be found on campus kissing various male students but will slap Jimmy if found kissing another student.

Angie Ng

Voiced by: Sue Jean Kim

• All Asians Know Martial Arts: Averted in her hard-to-hear fighting quotes.
  I don't know Kung Fu, but I'll still kick your ass!
• All Guys Want Cheerleaders: She's one of the first girls that Jimmy has the option to kiss, and is also a cheerleader.
• Bespectacled Cutie: Angie wears glasses and she's usually one of the nicest girls on campus.
• Gossipy Hens: Unlike her friend Christy though, the rumors she discuss tend to better reflect current events and are overall more grounded in reality.
• The Hyena: Often laughs and giggles, though it's often nervous laughter.
• The Klutz: Falls on her ass while jumping during cheerleading practice and her cheer animations are notably more delayed than the others.
• Mirthless Laughter: She laughs when someone flirts with her and makes her nervous, when someone scares her, and sometimes just when she can't think of anything to say or do.
• Nice Girl: One of the friendlier and more innocent students on-campus. When she sees other students fighting, she criticizes them and tries to get them to stop rather than cheer them on.
• Token Minority: Angie is the only Asian student at Bullworth.
• "Well Done, Daughter!" Girl: She constantly stresses out over getting good grades and not disappointing her mother.

Christy Martin

Voiced by: Maine Anders

• Beware the Nice Ones: She's bubbly and friendly. She also talks about setting the school on fire, claims she can use her tie as a garotte, and made a girl run away by spreading a rumour about her.
• Fiery Redhead: Her fiery-ness is much more muted than that of her brother, but if she gets pushed too far, as described above she can get vicious.
• Gossipy Hens: Judging by her dialogue, Christy seems to be very fond of spreading rumors. Some of the things she says indicates she is the one creating pretty much all of it.
• Heterosexual Life-Partners: With Angie.
• Redhead in Green: It's just coincidence that Christy has red hair and that the Bullworth Non-Clique uniform is a shade of green, but she does fit the letter of the trope.

Constantinos Brakus

Voiced by: Mathew Stadelman

• Clothes Make the Superman: As the mascot with the full outfit on, he becomes a boss and has a couple moves to make him at least on-par with the Jocks. He even shares Russell's charging headbutt, albeit a much less effective version of it.
• The Eeyore: He seems to perpetually be in a bad mood.
• Groin Attack: One of his attacks while wearing the mascot outfit.
• Karmic Butt-Monkey: He's such a jerk—sullen and unpleasant at best, and a bully and thief at worst—that you're more likely to have a laugh at his expense than sympathize with him when things go wrong for him. And they do so regularly.
• Sitcom Arch-Nemesis: From his pathetically jerkish attitude, to the number of times you have to beat him up in the story and side missions, Constantinos was pretty much designed for this role!
  Constantinos: (When Jimmy frightens him for the Bullworth Mascot Outfit) I HATE YOU, HOPKINS!!!
• Small Role, Big Impact: Although Constantinos isn't tied to any cliques, and ultimately doesn't play a major role in the battle between Jimmy and Gary, he does make quite a few prominent appearances in the story; the first being when he steals Eunice's chocolates in one of the first missions, causing Jimmy to go after him to take the chocolates back. He also appears as the subject of "tutorials" for how to use Taunts learned from English Class (where he tries to pick a fight with Jimmy, only for Jimmy to tell him to shove off), and appears as the Bullworth Mascot during Chapter 4 (where Jimmy eventually needs to mug him for the Mascot Outfit)
• Sticky Fingers: Steals chocolates from Eunice early on. Later steals some comic books from the comic book store.
  • Laser-Guided Karma: When he steals the chocolates, you can pay for them, but there's also the option to beat him up, Bully him, or shove his face right into the toilet for a swirly. When he steals the comic books, you HAVE to knock him off his bike before he gets back to school with them.
• The Stool Pigeon: He's the only older kid who actually tattles to the prefects.
• Strong as They Need to Be: An extreme example as he's usually one of the weakest students on campus, but when he dons the mascot outfit, he's even stronger than the jocks.
• Took a Level in Badass: As a non-clique student, he's a shrimp who steals from others, summons prefects when his health is low, and an overall downer who overestimates himself. By chapter 4, his battle strategy while donning the mascot costume is on par with Russel and can be a difficult fight for unprepared players.
• Unblockable Attack: Two of them when he is the Mascot—The first one has him flail his limbs and then deal a Groin Attack. The second one is headbutting his opponent with the horns on his costume.
• Unknown Rival: Jimmy doesn't even acknowledge the fact that Constantinos is always on the receiving end of his humiliation.

Eunice Pound

Voiced by: Cody Rose Lindquist

• Abhorrent Admirer: But you can still make out with her if you wish.
• Big Eater: "Ever been kicked out of an all-you-can-eat buffet?"
  • She's also the only girl who will only kiss you if you giver her a box of chocolates rather than flowers like all the other girls.
• Boring, but Practical: She looks very ugly, fat, unflattering hairstyle and with very thick voice, but at least Jimmy can kiss her for health bonus even if he wears clothing that makes other characters laugh at him.
• Girls Love Chocolate: She adores chocolate and will you kiss you if you give her a box of it.
• Gonk: Not only is she fat, but she has an unflattering hairstyle and a very husky, stupid-sounding voice.
• Hidden Depths: Her free-roam quotes hint that she is insecure and unhappy, effects from her weight, and talks about dieting and doing sports to shed it. Despite this, she believes things will be better for her soon.
• Jerkass: If her appearance doesn't put you off, her rudeness during conversations will. She does admit she's unforgiving, though. Also, when you first enroll in the school, she'll bully you, unlike any other girl.
• Noodle Incident: During "Save Algie" you find her coming out of a bathroom stall. From a boy's bathroom. Accompanied by Pedro. There's no explanation given.
• Soundtrack Dissonance: Every mission that ends with Jimmy kissing a girl, a jazzy Sexophone plays, but in "Movie Tickets" in where Jimmy is forced to kiss Eunice, the same sexophone plays despite being one of the ugliest girls in the school.
• Ungrateful Bitch: She won't accept flowers if you try and give them to her.

Gloria Jackson

Voiced by: Lea Ostner

• Black and Nerdy: Though she's really more just extremely scholastically-oriented rather than socially awkward and into dorky hobbies like the Nerds clique.
• Child Prodigy: Unlike most of the other supposed geniuses in the school she really is that smart, and usually pleasant enough to avoid being an Insufferable Genius.
• Likes Older Men: Downplayed—She mentions Oscar Wilde is attractive and has a very obvious crush on Jimmy, judging by responding to her positively.
• Orphaned Reference: Her maturity is possibly a leftover from her Beta counterpart, where she was around Jimmy's age and was able to be kissed by him.
• Out-of-Character Moment: During the mission "Rudy The Red Nosed Santa", her tone of voice changes completely, her Purple Prose is gone, and she talks extremely fast.
• Retcon: Gloria was originally intended to be a teenager like Angie and Christy—lines of dialogue for kissing were found in her data files. In a lot of her less likely to be heard dialogue, she has a slightly deeper and smoother, more mature sounding voice, and an errand has Constantinos express romantic interest in her. No information at all as to why she was changed to a little kid.
• Sesquipedalian Loquaciousness: Often talks like this.

Gordon Wakefield

Voiced by: Unknown

• The B Grade: Constantly complaining about this—even thinking Galloway should be fired for daring to give him one. No sign he actually deserves any higher.
• Big Ego, Hidden Depths: One of the few aversions among the cast's big heads. Most other characters with an inflated opinion have some redeeming traits or insecurities—Gordon just thinks he's that great.
• Casanova Wannabe: He knows he's a good kisser. He's practiced for years on his arm.
• It's All About Me: Doesn't understand the fuss about equality, brags about his handsomeness, and can often respond to other students' musings by saying "that's great, but not as great as me." He can't stand for positive words to be said about anyone but him.
• Jerkass: Probably the most unpleasant of the non-clique students. He's far more contemptible a guy than a lot of clique members.
• Miles Gloriosus: Boasts of his courage and fighting skills but is a massive coward in fights and can frequently be seen crying in fear on the Ferris Wheel.
• Small Name, Big Ego: He's very arrogant, plus he believes he's much better at fighting and kissing than he really is.
  Gordon: Can't believe she asked me that. Of course I'm the center of my universe! Sheesh!

Ivan Alexander

Voiced by: Cohlie Brocato

• Against My Religion: Tried using this for homework.
• Heavy Sleeper: Always yawning, talking about naps, and sleeping.
• Hidden Depths: A throw-away line indicates an interest in cinematography.
• Hypochondria: Rabies, leprosy, heart attacks, high blood pressure... he thinks he can get them all.
• An Odd Place to Sleep: Naps in the boiler room.
• The One That Got Away: Really misses his ex-girlfriend.
• Ow, My Body Part!: "Ow, my spleen!"
• Two First Names: Ivan and Alexander.

Karen Johnson

Voiced by: Cai Oglesby

• Nice Girl: One of the friendlier students, and lacking any serious negative feelings or moral defects. Does not approve of violence.
• Passionate Sports Girl: Her main schtick. Most of her dialogue revolves around her many athletic interests and complaining Bullworth doesn't let her play as many sports as she wanted.
  Karen: Is four teams too many to be on?
• Sweet Polly Oliver: Allegedly tried dressing up as a boy so that she could play on Bullworth's boys-only sports teams.
• Tomboy: Downplayed. Her main interest is sports, but she doesn't act particularly boy-ish otherwise.

Lance Jackson

Voiced by: Dylan Schneider

• Black and Nerdy: Played with. Has nerdy interests, but lacks the social awkwardness of the nerds and decries how reading has obtained nerdy connotations.
• Break the Cutie: Downplayed. Lance is a generally nice, compassionate and supportive guy, but a number of his quotes seem to imply he's nearing a breaking point.
  Lance: I transpose everyone else's problems onto myself! And it's like a cancer, it's eating me alive!
• Nice Guy: Arrogance aside, he's generally one of the more pleasant students on campus, always supportive of others whether they're complaining or bragging, and he hates senseless violence even when personally participating in a fight.
• Only Sane Man: Views himself as this.
• Small Name, Big Ego: Downplayed, mostly. Although he's not as narcissistic as Gordon, Lance can be very haughty and arrogant. Unlike Gordon, however, his own ego seems to be grounded in reality.
  • He actually lampshades his own tendency to judge others without judging himself in his "complaining" dialogue.
• Straight Man: If you think about it, Lance is the most normal character in the entire game. He just has such a minuscule role it doesn't show much.

Melody Adams

Voiced by: Shannon Amabile

• Bitch in Sheep's Clothing: About 80% of what comes out of her mouth is about how much she loves school and how well she behaves herself, and most of the rest is complaining about other people not being the same way. But she's by far the nastiest of the little kids. She's also the student who catches Jimmy in the girls dorm during a mission.
• Bratty Half-Pint: She's the stereotypical unbearable goody-two-shoes.
• Precision F-Strike: It's usually tough to get Melody mad enough at you to fight, but her dialogue for beginning an attack? "Bring it, bitch!"
• Precocious Crush: Has a very obvious one on Jimmy himself.
• Teacher's Pet: Not to Sheldon's extent, but she's fairly close, being the one who pulls the fire alarm during the aforementioned mission.
• Troubling Unchildhood Behavior: A relatively mild example, but it's jarring to hear her threaten to make someone her bitch.

Pedro de la Hoya

Voiced by: Daniel Tay

• Ambiguously Brown: Has a Spanish name, and appears to have a slight tan. His accent is anything but Hispanic. An early screenshot showed him with paler skin, pale hair and freckles—it seems he was changed to Hispanic at the last minute because there were so few Hispanic characters in the game.
• Hero-Worshipper: He looks up to Jimmy to the point of calling him "Sir".
• Momma's Boy: Maybe not to the extent of Algie, but he's close.
• Noodle Incident: At one point you find him in a bathroom stall with Eunice. No explanation given.
• Out-of-Character Moment:
  • He assigns Jimmy two errands—one to put a "Kick Me" sign on someone and another stuff people in trash cans—and acts a vicious brat while giving the errands. This brattiness isn't reflected in any other aspect of his character or in any of his dialogue, and he even has a couple other errands he assigns while under his usual personality.
  • During "Rudy The Red Nosed Santa", he also acts like a brat who thinks he "never gets what [he] want[s]". Even is voice is seriously different. Justified, as his original actor didn't return to voice him.
• Pint-Sized Powerhouse: You wouldn't think so, but he can occasionally be encountered fighting a bully like Trent, and can easily hold his own — usually getting several shots in before he gets hit and the prefects come running.

Ray Hughes

Voiced by: John Walker

• The Berserker: He refers to his one attack as a "Berserker Barrage", but said attack is one shove.
• Mr. Imagination: He likes to imagine himself doing things he's seen in movies or read about in books, and occasionally blabs out what he's imagining, like claiming to be an undercover cop investigating underage drinking parties.
• New Transfer Student: He was this a while before Jimmy came along. He still finds it difficult to fit into school.
• Nice Guy: One of the few students in the school who is actually pretty decent.
• Official Couple: To Eunice, by virtue of being the only boy that is programmed to be seen holding hands with her.
• Unblockable Attack: His shove, which is also his only attack.
• Unskilled, but Strong: He may not know any fighting moves other than a shove and he may not try it often enough during a fight to actually win said fight, but his shove does do damage to even a blocking opponent.

Sheldon Thompson

Voiced by: John Magaro

• Asshole Victim: He mentions being the butt of many pranks in the school (and the player can do so, too), but seeing his obnoxious attitude, he has it coming.
• Bratty Half-Pint: An obnoxious goody-two-shoes teacher's pet like Melody.
• Catchphrase: "Hi! It's me, Sheldon!"
• Pint-Sized Powerhouse: You wouldn't think so, but he can occasionally encountered fighting a bully like Trent, and can easily hold his own.
• Teacher's Pet: Most of his dialogue is him bragging about how he helps the teachers and how they are his "friends", yet both Hattrick and Crabblesnitch find him annoying.

Trevor Moore

Voiced by: Adam Serwer

• Only Sane Man: Views himself as this and can't wait to get out of Bullworth Academy.
• Out-of-Character Moment: For some reason during Halloween and specifically while he's in his werewolf costume, Trevor will have the A.I. of a Bully. This means the normally docile student will be friendly towards other Bullies, hostile towards any other student, especially Jimmy and the Nerds and will even adopt the Bullies' sloppy Brawler fighting style.

As a whole

• Apple for Teacher: Their rarely-seen long-range attack is based on this, where they throw apples at their target if they can't get to them.
• The Bad Guys Are Cops: They're the police force within the game and it's shown that they're not doing their jobs for the sake of law and order. Seth and Karl use their authority to abuse the students and Edward's using his authority to pad out his resume (and seemingly flirt with girls). The only one who seems mildly interested in fulfilling his duties is Max, who seems genuinely interested in pursuing a career in law enforcement.
• Cutscene Incompetence: The prefects are good at catching misbehaving students, however, during Complete Mayhem, Russell is able to chase off Seth and Max.
• Jerkass: Many of them became Prefects for selfish reasons and treat the other students with contempt. The only way to get them to ever be nice to you is by wearing the Orderly Uniform.
• Laughably Evil: While they're undeniably a bunch of power-tripping thugs, it's hard not to crack a smile at their hammy dialogue, Black Comedy-laden threats, and generally larger-than-life personalities.
• Leitmotif: The song that plays whenever Jimmy is being chased by one or more Prefects — a fast-paced, funky theme that's heavy on the wah pedal and horns, not unlike what you may hear when watching a 1970s cop show or movie.
• Not So Above It All:
  • The game is programmed to have every NPC respond to "Kick Me" Signs when applied to someone, and the Prefects are no different.
  • During Complete Mayhem, the prefects are absent and inside the school building. They confiscate Jimmy's slingshot and are chased off by Russell. They do so not to stop any chaos but because "Weapons are for Prefects only!", showing that they've fully agreed to Gary's riot.
• One-Hit Kill: In a sense. If your wanted meter is in the red, getting grabbed by a Prefect means that you're going straight to Dr. Crabblesnitch's office with no chance of escaping or fighting back.
• Screw the Rules, I Enforce Them!: Plenty joined the Prefects to give them the excuse to bully and beat students with the school's justification.
• Ungrateful Bastard: Even after Complete Mayhem, they still mostly treat Jimmy with contempt. Oddly, if Jimmy wears the Orderly Uniform, they'll be pleasant to him.
• Younger Than They Look: Despite seeming to be at least in their thirties, Seth and the rest of the prefects are actually seniors close to graduating, which would place them all about seventeen or eighteen years of age.

Seth Kolbe

Voiced by: Unknown

• Ax-Crazy: And HOW. When he isn't "merely" being a smug bully, he sounds like he's almost looking for an excuse to flip out and beat kids up just because he's that much of a violent psychopath.
• Dirty Cop: Seth is mostly into being a prefect because he enjoys the power. If he actually has to do any prefecting, he's as likely to just lash out at random bystanders as he is to actually pursue the rulebreaker. Or in addition to pursuing the rulebreaker.
• Hair-Trigger Temper: While he's a power-tripping jerk who will gladly brutalize students just because, some of his dialogue indicates that his violent tendencies are at least partially rooted in serious deep-seated anger issues that he doesn't know how to deal with.
• Hypocrite: Seth likes to call the kids "evildoers". Pretty rich coming from someone who enjoys abusing his authority to pick on innocent people.
• Informed Attribute: Almost all of his dialogue consists of threatening to beat anyone who breaks the rules. However, he never physically attacks any of the students (outside of throwing the occassional running punch to stop them in their tracks) and instead uses the same restraining technique the rest of the prefects use. His dialogue is likely a leftover from the beta version of the game, where the prefects carried batons and actually did use them on the students.
• Jerkass: Constantly threatening students with beatings, and really seems to enjoy it to boot.
• Large Ham: EEEEEEEEVILDOER!

Karl Branting

Voiced by: Wilhelm Lewis

• Accent Slip-Up: Karl's slow and carefully enunciated speech occasionally lapses into a somewhat standard African-American accent when he's angry or stressed, faintly implying that he's trying to sound less Black as a career booster.
• Dirty Cop: Thankfully not as abusive or power abusing as Seth, but he's definitely doubleplus ungood.
• Jerkass: Arguably as bad or worse than Seth - Seth may be more aggressive, but he mostly lashes out at random whereas it's implied that Karl picks a victim and does everything he can to make their life miserable.
• Large Ham: He was definitely designed with this role in mind.
  Good Lord! I appear to have been knocked over!
  Argh! THAT WAS BELOW THE BELT!
  Argh! That is disgusting and unhygienic!
• The Napoleon: Another mild case — he's about a head shorter than the other prefects and occasionally makes a comment that makes it sound like he's self conscious about it.
• Purple Prose: Downplayed — he drags out his sentences as long as possible and enunciates everything he says, but most of his dialogue doesn't have any traces of archaic, complex wording.
• Scary Black Man: Or rather, scary black teen, but he's still a strict and corrupt authoritarian who gladly abuses the power he holds over other students.
• Token Minority: The only black member of the Prefects.

Edward Seymour II

Voiced by Ryan King

• Bring My Brown Pants: One of his knocked-out lines: "I need new underwear..."
• Four Eyes, Zero Soul: The sole Prefect to wear glasses, and he's every bit as ruthless and overzealous as the rest.
• Large Ham: Kneeeeeeeeeeeel before Edward! Ragh!
• Nerdy Nasalness: Unlike the other, far more intimidating-sounding prefects, Edward has a high, nasally, almost dweebish-sounding voice. It's fitting, seeing as how he's easily the dorkiest of the bunch.
• STD Immunity: Averted. He seems to have contracted... something. He didn't even know you could get a rash there... and it itches like crazy. He also calls himself a studmuffin constantly.
• Trademark Favorite Food: Hot dogs, apparently.
• Upper-Class Twit: Considering his family is rich, he's a member of the sailing and yacht club, and he brags about his numerous awards, it's likely Edward's just using his position to pad out his resume.

Max McTavish

Voiced by: Lenny Grossi

• Drill Sergeant Nasty: Appears to be an in-training version of this. His style of imposing authority consists of berating students with gross insults such as "toilet stain" and "smear wipe."
• Graceful Loser: In one of his knocked-out lines, he actually tells the winner "You should become a Prefect."
• Knight Templar: He does, at the very least, genuinely care about maintaining order at Bullworth and dealing with troublemakers who step out of line. Though it doesn't make him any less of a loud-mouthed jerk whose approach to discipline is to terrorize students into keeping their noses clean.
• Pet the Dog: One sidequest has you give Max some toilet paper since he's stuck in a bathroom stall without any on hand. Help him out, and he's not only genuinely grateful, but he pays you for your trouble.
• Punny Name: "You'll be prosecuted to the max!"
• Reasonable Authority Figure: If only compared to the other prefects — he may be a total Jerkass, but he's the only one interested in law and order, and unlike the other prefects, is actually interested in going on to a career in the military or police. Edward is self-absorbed, and Karl and Seth are malicious bullies.

As a whole

• Badass Teacher: They're all statistically formidable with high stamina and health bars on par with the tougher clique leaders as well as immunity to any grapple attempts.
• Head-in-the-Sand Management: Aside from Mr. Galloway and Ms. Philips, they don't particularly care for the well-being of the students and will only intervene if they witness trouble for themselves. Mr Burton even encourages bullying under the belief that it builds character.
• Immune to Flinching: They can sometimes tank hits from Jimmy without any reaction, allowing them to apprehend him mid-combo.
• Non-Giving-Up School Guy: If any of the staff are provoked in free roam. They have tons of health larger than the Prefects and are authority figures who can instantly bust you if the trouble meter is high enough. And just like the Prefects, getting caught by them automatically sends you to class if you have one active.
• No-Sell: To grapple attempts.
• Stern Teacher: Regardless of their actual personality, whenever they appear in free roam they will act contemptuous and dismissive towards all students when interacted with.

Dr. Crabblesnitch

Voiced by: Ralph Gunderman

• Adults Are Useless: While he means well, he's completely blind to just about everything wrong with the school he runs. Fortunately, Jimmy persuades him to help make Bullworth Academy a better school, such as firing Mr. Hattrick and Mr. Burton.
• Advertised Extra: Crabblesnitch often appears in the promotional material exchanging a glare with Jimmy but he has minimal involvement in the plot.
• All Psychology Is Freudian: Downplayed. He seems to think that most of Jimmy's problems can be attributed to his mother - which is a completely reasonable conclusion to draw.
• Animal Motif: His office has bird imagery and Dr. Crabblesnitch is known for looking down on others and being aloof, as he doesn't see bullying as harmful and overlooks the incompetence of his staff. He's also described as a noble and serious figure by others and his nose resembles a bird's beak/nare.
• Big Bad: Subverted. Though he initially appears to be the main antagonist of the game (and was originally intended to be), it ultimately turns out that he's a Reasonable Authority Figure and that Gary Smith is the real Big Bad.
• Born in the Wrong Century: He seems to believe the 1950s never ended, going by his style of dress and his attitude towards bullying.
• Brutal Honesty: He never minces his words, and lets students know if he judges them as unpopular or troublesome. He has no problem revealing his biases towards the jocks and preps and his dislikes towards nerds and greasers.
• Condescending Compassion: His attitude towards nerds, greasers, Jimmy, townies, and the like whenever they are victimised.
• Deadpan Snarker: Sometimes. For example, if Jimmy is failing at English when brought into Crabblesnitch's office, he might quip "too stupid to speak your native language properly."
• Dean Bitterman: Downplayed. He stays on Jimmy's case, but doesn't even consider to expel him until he has no choice due to Jimmy's vandalizing of City Hall in broad daylight.
• Distressed Dude: In the climax, Gary somehow ties him up and leaves him to rot in his office.
• Do Wrong, Right: His voice files reveal he is not opposed to beating nerds up or keeping them in their place, but he can criticize Jimmy for going too far or getting caught.
• Game-Over Man: He'll lecture Jimmy the first couple of times you're "Busted". After that, he sentences Jimmy to menial labor.
• Get Out!: Jimmy gets busted for vandalism in the game's final act, which results in his expulsion. At first, Crabblesnitch tries to dismiss Jimmy civilly, but when the youth presses on with denouncing the school and its faculty, the Head angrily throws him out.
• Good All Along: He turns out to be a Reasonable Authority Figure at the end of the game.
• Good Is Not Nice: While he can be an asshole, Crabblesnitch by no means a villain; he reveres traditional mores like self-discipline, dedication and the value of hard work, which is why he gives Jimmy and the other delinquent kids every possible chance to stay in school and reform themselves.
• Head-in-the-Sand Management: Crabblesnitch is completely oblivious to Bullworth's massive bullying problem, simply brushing it off as "school spirit". Before expelling Jimmy, he promotes Gary to head boy and believes he's not afraid of being an unpopular leader, ending up with Gary using that trust to tie him up to cause a riot. After overhearing Gary's Evil Gloating, he expels him and pardons Jimmy.
• Horrible Judge of Character: Believes Gary is a responsible kid despite his reputation saying otherwise, not only that, but he also can't even see that almost every student in the school is a criminal or irresponsible pieces of shit and thinking the worst out of Jimmy despite Jimmy trying to show him reality at the school he runs.
• Nostalgia Filter: Always longing for the good old days, such as when students were always expected to respect adults and authority.
  • Nostalgia Ain't Like It Used to Be: His views tend to fog how he sees things at Bullworth. Jimmy causing a ruckus is troublesome but any other form of hazing is simply school spirit, noting that back in his day, "[they] thought nothing of castrating the new boys!"
• Pet the Dog:
  • He lets off Mr. Galloway with a warning rather than firing him once it becomes apparent his drinking on the job is the result of Mr. Hattrick's relentless bullying.
  • He also gets a long string of these during the ending, where among other things he praises Jimmy for exposing Gary, promptly fires Burton and rescinds Zoe's expulsion after hearing the situation behind it, promotes Pete to head boy at Jimmy's suggestion and finally, decides not to expel Jimmy after all.
• Politically Motivated Teacher: Downplayed—his dialogue occasionally shows a strong dislike of socialism, an adherence to social classes, his longing for the good old days, and reverence of authority can be used to make guesses about his political views. He has no qualms about letting these views out or guiding his actions.
• Rank Scales with Asskicking: An ex-Prefect himself, he will not hesitate to bust you on campus. He's also the only NPC who never runs out of stamina and has a healthbar that is four times the size of the average adult and Prefect. Good thing he only appears once and is usually contempt to remain in his office.
• Reasonable Authority Figure: If you can actually get his attention, he does the right thing. Getting it is the hard part though...
• Selective Enforcement: If Jimmy does it, it's fighting and violent conduct. If anyone else does it, it's school spirit and hijinks. He makes this distinction clear in your second conversation with him.
• Straw Character: Subverted; his doggedly old-fashioned conservatism is mostly what makes him an unpleasant hardass for Jimmy to deal with, but it's also the source of his sympathetic qualities that compel him to repeatedly give kids like Jimmy the chance to remain in school.
• Toxic Friend Influence: He views townies, nerds, carnival freaks, and greasers as bad sources of influence, among others.

Mr. Burton

Voiced by: Michael Boyle

"Ahhh, this is worse than when I got hazed!"

• Abusive Parents: His father apparently beat him constantly as a child and he's still scarred to this day. This might explain his arrogant behaviour towards his students.
• All Men Are Perverts: One mission of his involves the main character sneaking into the girls' dorm to steal their panties to give to him.
• Career-Ending Injury: Hurt his knee while trying to become a pro football player, had to become a coach at Bullworth instead. He's quite bitter about it.
• Casanova Wannabe: Desperately seeking a girlfriend, yet doesn't realize no one wants to hook up with him.
• Covered in Gunge: Ends up covered in feces when Jimmy pushes the port-a-potty Mr. Burton is in off the ledge as revenge for getting Zoe expelled.
• Creepy Gym Coach: He's very interested in the female students and asks Jimmy to get panties for him.
• Dirty Old Man: Buys porn, recruits Jimmy to steal girls' panties, gets Zoe expelled because he hit on her and she refused him. He was even more so in the beta version, where one errand involved photographing him trying to seduce women.
• Drill Sergeant Nasty: Gym teacher version.
  Mr. Burton: Ah, dodgeball! How I love the sound of boys crying in the morning!
• Ephebophile: The game doesn't outright say it until the Final Showdown but it was pretty apparent that Mr Burton has been lusting for the girls in Bullworth Academy. He tricks Jimmy into stealing the girl's laundry for him under the excuse that he forgot to collect them for laundry day but it's only when Jimmy meets Zoe in chapter 5 that he learns that Mr Burton sexually harrassed her and got her expelled when she reported his actions.
• Fat Bastard: Despite being a gym teacher, Mr Burton isn't exactly the fittest man on campus. He's also pretty nasty to his students, and is a dirty creep to boot.
• Greater-Scope Villain: Although it's never said outright in the game, Mr. Burton is actually responsible for the Jocks being so bloodthirsty as it is rumored that he's been giving them steroids and he outright says to Jimmy that he encourages bullying within the Jocks because it builds character and makes men. Then there's the fact that he had Zoe expelled after she tried to report him for sexually harassing her.
• NO INDOOR VOICE: Constantly loudmouthed even when trying to deny walking out a store selling explicit magazines.
• Out-of-Character Moment: Even though he encourages both bullying and fighting, he'll still bust people for doing so, even jocks.
• Paper-Thin Disguise: In "Panty Raid", he doesn't even bother disguising himself besides wearing a fishing hat and a pair of black shades. Bonus points for the fact that the Bullworth Academy crest is clearly on his trousers.
• Pet the Dog: The more gym classes Jimmy passes, the more Mr. Burton comes to respect him, eventually professing that he's tougher than he originally thought.
• Villain of Another Story: He's Zoe's archenemy because he sexually harassed her while she was at Bullworth Academy, eventually getting her expelled when Zoe tried to report him for his actions.

Mrs. Carvin

Voiced by: Patricia Kilgariff

• Born in the Wrong Century: Extremely outdated clothing, dislikes modern society, and mentions that she hasn't changed her hair in about 30 years.
• Pet the Dog: After Jimmy exterminates all the rats in "Rats in the Library", she offers to "forget" about any late fees Jimmy would have accumulated for unreturned books. Jimmy remarks that he already has before thanking her.
• Scary Librarian: Invoked. She even considers wearing glasses for the sole purpose of making herself look more intimidating.
• Why Did It Have to Be Snakes?: She has a fear of rats. One of the storyline missions in the game for the Nerds involves killing an infestation of them in the library for her.

Miss Danvers

Voiced by: Lori Funk

• Chekhov's Gunman: After Jimmy vandalizes the town hall, she can be heard scorning him for it, although she cannot be seen. Later in the chapter, she calls him to the front office so he can be expelled for it. For sharp-eared players, this could be an Oh, Crap! moment, as it implies she saw what you did.
• Jerkass: The PA announcements around the school shows she really hates the students (apart from Sheldon and Derby), and refers to them as "little monsters". She goes as far as insulting Beatrice when calling her to receive her college applications.
  Miss Danvers: (through PA) Your attention please... Oh, nevermind, you little monsters.
• Sassy Secretary: To anyone who isn't Dr. Crabblesnitch.
• Sexy Secretary: While she's by no means an unattractive woman, she's slightly outside of the age range that usually comes with this trope. She looks like she might have fit this role better ten or fifteen years ago. Interestingly, at one point in Bully's development she was younger and hotter, as seen in this old image◊.
• Single-Target Sexuality: As mentioned above, she's obsessed with Crabblesnitch to the point she talks about him over thirty times in her dialogue sets.
• Sycophantic Servant: To Dr. Crabblesnitch.
• Yes-Man: She would never even think of contradicting Dr. Crabblesnitch on anything.

Edna

Voiced by: Kathy Rossetter

• Affably Evil: She may be a disgusting slob who spits and coughs into the cafeteria food and is perfectly willing to drug and rape a man she's in love with, but she's pretty friendly to Jimmy in her own crude way.
• Brawn Hilda: Not only her design is horrendous (even worse with makeup in "Cook's Crush" side mission), but also she has a deep manly voice.
• Double Standard: Rape, Female on Male: Asks Jimmy to drug Dr. Watts with a sedative so she can do stuff to him. When Dr. Watts is drugged, she tells him that he's going to be shown "everything she knows about chemistry... and a little biology!".
• Everyone Has Standards: As disgusting as her cooking is, in an earlier version of The Big Game, she'd exclaim how disgusting it is if Jimmy is caught "spiking" the jock's cooler.
• Fat Bitch: A morbidly obese cafeteria lady who takes pride in the way she makes her food as disgusting as humanly possible.
• From Bad to Worse: According to the pointer below, she has a nightmarish looking face, but in "Cook's Crush" side mission, she applies makeup in her face, it looked even more nightmarish.
• Gonk: Her character design is quite grotesque. It only gets worse when she attempts to apply makeup to herself, making her look even worse.
• Good Is Not Nice: To Jimmy at least, unlike most staff members and authority figures. Edna is quite civil and tries to be as friendly as possible to Jimmy. However, Jimmy is still disgusted by her.
• Lethal Chef: Quality isn't exactly a priority at Bullworth, but using long-expired meat and baking a cat into a casserole?
  The only person who is allowed a weapon on campus is me, and I use it to make dinner!
• Nightmare Face: Her face is incredibly nightmarish (even more so than Eunice) and her makeup it gets worse.
• Noodle Incident: Apparently she accidentally cooked one of Ms. Philips' cats into a casserole. Later on, the latter leaves a notice about it on the bulletin board.

Mr. Lionel Galloway

Voiced by: Robert Stanton

• Actually Pretty Funny: If Jimmy spells out a swear word on his papers, Galloway will actually laugh before telling him he can't use that word.
• Affectionate Nickname: Ms. Philips calls him "Gally-bear".
• The Alcoholic: Driven to drinking by relentless bullying over the course of years from Mr. Hattrick.
• Benevolent Boss: Teacher variant. Being one of the few adults in the game (or the world, depending how you look at it) that isn't useless, the students actually regard him with genuine respect because of how much he genuinely cares about his students (special mention for praising students giving each other answers to class assignments as "helping" rather than punishing them for "cheating" because of the positive impact it has on their grades). He's also the only teacher that Jimmy sincerely addresses as "sir", despite having to mop him up a few times, for exactly this reason. He also admits in idle dialogue that he's saddened by the low morale of his students and wants to help them "care about themselves".
• Cool Teacher: His in-class dialogue has him offer advice to students, such as doing their homework assignments in class so they'll have more free time in the evenings and hearing that students have been helping each other with coursework and encouraging it, noting that they're learning the value of teamwork. He's also quite friendly with Jimmy and is grateful for all of Jimmy's help.
• Everyone Has Standards: He may be a nice guy but he has a notable hatred of Mr. Hattrick, for justified reasons.
• Hidden Depths
  • His idle dialogue has him express some self-awareness about his drinking problem, stating he'll become the next hobo on campus if he doesn't control himself.
  • Galloway can also express hatred for Derby Harrington, expressing the idea that he might fail Derby regardless of the threats made by Derby's father and Dr. Crabblesnitch because Derby has been skipping classes.
    Galloway: Just maybe, I'll fail Derby Harrington in spite of what his father and Dr. Crabblesnitch might say. God knows he deserves it.
• Insecure Love Interest: Implied. He's genuinely surprised to learn that Ms. Philips is interested in him and he commits himself to a mental hospital to better himself after he was convinced by Hattrick that he was a burden to everyone around him.
• Meaningful Name: His surname, Galloway, is a breed of cattle found in Scotland. A fitting name for someone who works at Bullworth academy.
• Mr. Vice Guy: He may be an alcoholic, but he is so kind and nice that he encourages his own students to do their homework assignments in class so that they can have more free time in the evening, among other things.
• Nice Guy: Out-of-Character Moment aside, he's one of the friendliest teachers in Bullworth Academy.
• Out-of-Character Moment: Despite being a Cool Teacher who is usually nice to Jimmy, if you encounter him in free-roam mode and greet him politely, he will rudely tell him off. Along with every other teacher, this changes in the playable epilogue. Zig-zagged since when he bust Jimmy, he asks why such a good boy like him would be so violent.
• Reasonable Authority Figure: One of the few in the school who is actually sympathetic and cares about his students. He holds the rich kids and jocks to the same standards as everyone else, but is fair to them too—Luis Luna tells an anecdote about getting a good grade on an English paper because Mr. Galloway talked him into writing about football. He also doesn't reprimend Jimmy for using a swear word on test, and complements him for such young school spirit.
• Younger Than They Look: Is only 34 years old. The stress of the job and his alcoholism makes him look at least ten years older.

Mr. Hattrick

Voiced by Charles Turner

• Abhorrent Admirer: It's suggested that Hattrick also has feelings for Ms. Philips but she finds him repulsive and evil for how he treats people.
• The Bully: He enjoys harassing the students and Galloway, with the latter's drinking problems stemming from Hattrick's abuse.
• Cold Sniper: Some of Pedro's dialogue indicates he was a sniper during the Korean War. He could be responsible for the friendly fire incident that destroyed Mr. Grant's platoon in Korea.
• Fat Bastard: He's considerably pudgy, and is one of the nastiest characters in the game.
• For the Evulz: Comes from a wealthy family and has no financial need to keep his job at Bullworth—he stays there mainly because he enjoys bullying students and faculty.
• The Friend Nobody Likes: Of the faculty, Hattrick appears to be the most hated by his peers. Crabblesnitch is too aloof, Miss Danvers is too busy pining for her boss, Galloway hates him for bullying him, Ms. Phillips hates him for hitting on her and for bullying her boyfriend, and Edna has no qualms about contaminating Hattrick's food at Jimmy's request. According to Edna, Hattrick and Galloway have hated each other for a long time and it isn't the first time they've been at each others' throats.
• Jerkass: By far one of the biggest in the game. Generally unpleasant teach towards students. It says something that he's one of two teachers that Jimmy doesn't respect, before Burton.
• Large Ham: He's quite bombastic in his dialogue. Subtlety is definitely not his thing.
• Older Than They Look: Cut out dialogue suggests he is 48 years old, but by his looks, he seems to be a few years younger at best.
• Pet the Dog: He's actually relatively pleasant in Math class if you do well, though he won't hide his surprise if Jimmy manages to pass his class.
• Sadist Teacher: Doesn't think corporal punishment in school is adequate—he wants capital punishment.
  Children are like dogs! They only learn through frequent punishment!
• Satellite Character: His involvement in missions is based purely on his bullying Galloway. Downplayed in that he still has a minor role outside of that, being the math teacher.
• Scary Black Man: He may be obese, but he's also the physically largest character in the game and a former soldier. He was actually able to intimidate Russell into behaving himself, and none of the other teachers are willing to stand up to him.
• The Sociopath: A callous and sadistic man who loves abusing students and tormenting his fellow teachers. He's willing to manipulate Mr. Galloway into checking himself into a horrible asylum, has no empathy for his late wife (who committed suicide), and the only positive relationship he has with Bullworth's student body is purely transactionary, with him selling test answers to the rich kids so he can get an easy payday.
• Villainous Rescue: At the start of the game, he intervenes to save Jimmy from getting beaten by Russell. Though it hasn't been made clear he's a villain himself at that point.

The Hobo

Voiced by Angus Hepburn

• Actor Allusion: One of the townswomen quips something about Mr. Grant having once been "the star of the Scottish Stage." His voice actor, Angus Hepburn, is Scottish and primarily a stage actor.
• All There in the Manual: Downplayed. His name is revealed to be Mr. Grant in hard-to-find dialogue by townswomen mention his name, and his file names are also Grant.
• Noodle Incident: The Hobo appears to really dislike Dr. Crabblesnitch. Some dialogue from the Nerds and Bullies in the game indicate he may have been a former teacher before being fired.
  • In the game, Grant mentions his platoon was destroyed during a friendly fire incident in Korea. Mr. Hattrick is mentioned to be a Korean War sniper. Seeing Hattrick's dialogue, it's possible he was responsible for the incident.
• Retired Badass: He was a veteran in the Korean War. In addition, all of the moves he teaches to Jimmy were part of his military combat training.
• Serious Business: He requires the transistor parts for a project he's making, before it's too late. It's revealed to do with aliens.
• Suspiciously Specific Denial: Miss Danvers announces over the PA system that the Hobo is NOT a fired former teacher and there are to be no rumors to the contrary.
• What Happened to the Mouse?: After retrieving all the transistors and teaching Jimmy his last move, he is slowly lifted into the sky by a tractor beam. He doesn't appear again, although the beam can still be seen at night.

Mr. Luntz

Voiced by: Sean Eden

• Child Hater: Constantly mutters about how much he hates the students and is thrilled when he gets an excuse to rough them up. He even says he's "allowed to hurt them as long as he doesn't leave bruises".
• Jerkass: Perpetually in a terrible mood and miserable about his lot in life, he dreams of taking it out on everybody else. Notably, if you get him to be polite with you (such as by wearing fancy clothes and haircuts when talking to him), he'll sound like he's downright struggling to be nice.
• The Starscream: Constantly plotting to take down Dr. Crabblesnitch, although it's unclear why or what he expects to get out of having done so.

Mr. Matthews

Voiced by: Unknown

• Adventurer Archaeologist: Apparently was this at one point in his life. We would have gotten that idol if it wasn't for the damn boulder.
• Nice Guy: The only bad thing you could say about him is that he's enthusiastic about geography to the point of being a little annoying—but he's still miles better than most of the other teachers in Bullworth.

Mrs. McRae

Voiced by: Susan Blommaert

• The Fatalist: She believes that life is misery and then you die and that's all there is to it, so why try to make anything better.
• School Nurse: The grouchy and unattractive Western version.

Neil

Voiced by: Jesse Lenat

• Catchphrase: "Shut up and get to work."
• Conspiracy Theorist: Obsessed with government plots. According to him, the Illuminati have taken control of the Western front and are plotting to eradicate Christianity.
• Delinquents: Was once upon a time the leader of the Greasers.
• Hot Teacher: According to the girls.
• Politically Motivated Teacher: Sometimes tries to get the kids to open their eyes to all the government plots he's worried about. He never gets far with it though, because he gets irritated and tells them to shut up and get to work.

Mrs. Peabody

Voiced by: Flo Salant

• Apathetic Teacher: Claims she has never been happy ever since she was five years old, and considers this to be unfortunate.
• Does Not Like Men: Wishes for Bullworth to be an all-girls school. Not only does she punish boys unfairly every chance she gets, she outright brags about it too.
• Gonk: Not to Edna's extent, but she has an unpleasant, pinched, hawkish face set in a perpetual scowl.
• The Pirates Who Don't Do Anything: Downplayed—While she's seen patrolling the girls' dorm (and the girls' washroom in one mission), her actual teaching role is unknown. It's been speculated that she's the Home Economics teacher since there's a Home Economics room but no designated teacher. However, there's no specific evidence for this.

Miss Peters

Voiced by: Saidah Ekulonah

• Beware the Nice Ones: While she's not so extreme so as to qualify as a Bitch in Sheep's Clothing, she has a nasty side that shows when she uses her power to fail Jimmy to get him to participate in the Pageant.
• Cool Teacher: Is very encouraging and polite.
• Granola Girl: Judging by the dreadlocked hairstyle and tie-dye outfit.
• Hippie Teacher: She has a more manipulative side, though.
• Sassy Black Woman: When she blackmails Jimmy into taking part in the Christmas Pageant.

Ms. Deidre Phillips

Voiced by: Blaire Ross

• Hot for Teacher: Just about every guy in the school.
• Innocent Fanservice Girl: She does a few poses during art classes and Jimmy's portraits get more and more "flattering". She also asks Jimmy for some favors and didn't realize that she was implying that she had feelings for him when, in reality, it was Galloway who caught her eye.
• Lady in Red: Dons a cleavage-revealing red dress for a date with Mr. Galloway.
• Mrs. Robinson: Inadvertently tricks Jimmy into thinking she wants a date with him. Instead, it turns out the date is with Galloway; she pinches Jimmy on the cheek and calls him cute. Lampshaded by the mission name “Here’s to you, Ms. Phillips” being a Shout-Out to the trope namer, The Graduate and its associated song by Simon & Garfunkel.
• Out-of-Character Moment: Just like Galloway, she's normally one of the nicest teachers on campus but attempting to interact with her in free roam will result in her insulting you at best. This changes in the playable epilogue.
• Reasonable Authority Figure: Again, one of the very few in the school.
• Single Woman Seeks Good Man: She and Galloway do end up in a relationship and it helps that Galloway is one of the more popular and affable teachers. That, and they share their hatred for Mr Hattrick.

Dr. Slawter

Voiced by: Kurt Rhoads

• Mad Scientist: He's not overtly insane or anything, but he's very morbid and death-obsessed, and he likes to get high on ethanol.
• Meaningful Name: He's the death-obsessed biology teacher. You do the math.
• Nightmare Fetishist: Slawter likes monstrous plants and other morbid scientific curiosities... provided they belong to him, of course.

Dr. Watts

Voiced by: Jarel Davidow

• Absent-Minded Professor:
  Dr. Watts: What are you all doing in here?! Oh, right. Class.
  • Understandable in this one case, since it's the first day of school. It's completely played straight in another class, where he says the students can turn in their assignments on his desk... before remembering he didn't GIVE any assignments to turn in.
• Double Standard: Rape, Female on Male: Let's just say the romantic tryst between Watts and Edna wasn't exactly consensual.
• Hallucinations: He appears to suffer from these quite frequently, having been exposed to chemical fumes in the labs for so long.
• Mad Scientist: A rare light-hearted, rather than evil, version.

Mr. Wiggins

Voiced by: Gary Yudman

• Absent-Minded Professor: Is very knowledgeable on history (especially European), but seems a bit spaced-out on everything else. He mumbles historical facts and debates historical questions with himself under his breath.
• Former Teen Rebel: Used to be a troublemaker when he was younger. He turned it around while at Bullworth and became a historian. At least the system worked well for one person...
• Minor Major Character: He has no role in the story, bar one minor appearance in a Scholarship Edition mission, and teachers don't spawn very frequently in free roam either. For these reasons, he's unknown to most players.
• Trivia: In-universe example: he spouts these under his breath. Did you know that the Spanish Armada had faster ships, but the English ships were more powerful? Or do you want to know how to tell the difference between Italian and Swedish meatballs? Just ask Mr. Wiggins.

Officer Monson

Voiced by: Mike Plant

• Have I Mentioned I Am Heterosexual Today?: "I always get my man!...That didn't sound gay, did it?"

Officer Ivanovich

Voiced by: Ron Reeve

• Police Are Useless: Kinda subverted he gives Jimmy a couple of errands to do jobs that he should do himself, but at least he made sure the jobs got done at all.

Officer Williams

Voiced by: Chad L. Coleman

• Dirty Cop: Double subverted—he's a nice guy and not openly corrupt, but an errand shows he has at least one corrupt dealing with Milhailovich, the motel owner.
• Glory Days: His days as a high school track star.
• Police Brutality: Averted. He doesn't seem to enjoy police brutality, or at least he takes care to cover that up.
• Reasonable Authority Figure: Seems to genuinely care for juveniles in Bullworth. He drops Jimmy off at school if he's caught during curfew or playing truant, and also warns him about the consequences of crime every time.
• Token Minority: The only black officer in Bullworth's police department.

Officer Morrison

'Voiced by: Jim Norton

• By-the-Book Cop: The only cop not shown to be engaging in corruption or police brutality.
• Momma's Boy: He's rather close to his mother and mentions her often. Sometimes he'll even call out to her when knocked out.
• Reasonable Authority Figure: He never abuses his authority and is an Authoritarian at worst. He also gives Jimmy two different side quests to help maintain the Tenements, even though the only people it'll be benefiting are the Greasers.
• Wholesome Crossdresser: Apparently he's wearing a bra and a girdle underneath that uniform and mentions shopping for lingerie. He's still one of the more noble members of the Bullworth Police Department.

Betty

Voiced by: Saetha Ebans

• Granola Girl: Sort of—she doesn't rock the hippy vibe but she's into natural living and organic products.
• Perky Goth: Dresses in all black and has black spiked hair with metallic blue highlights, but she's cheerful.

Mr. Carmichael

Voiced by: Douglas Keever

Nicky Charles

Voiced by: Roderick Covington

• Pretty Fly for a White Guy: Downplayed, but he works hip-hop lingo into his speech.

Mr. Moratti

Voiced by: Vincenzio Sanseviero

Mr. Oh

Voiced by: Andrew Pang

• Asian Speekee Engrish: During cutscenes he speaks American English with a generic accent, but during free roam he has a pretty painful stereotypical ghetto-Asian accent. Zig-zagged as well because some of these free roam lines are in the abovementioned generic acccent too.

Zack Owens

Voiced by: Adam Sietz

• Abhorrent Admirer: To Miss Kopke. Apparently he tried asking her out to a comic convention.
• Nerd Glasses: Wears round glasses, although they're a lot smaller than Algie's.
• Speech Impediment: Speaks this way as a result of his asthma.

Stan

Voiced by: Jon Young

• The Stoner: Outright stated to use marijuna, heavily implied to be under the influence when interacting with Jimmy.
• Suddenly Shouting: Usually slow speaking and relaxed, but if angered enough he goes straight to OUTRIGHT SCREAMING FURY! It's another implication that he's under the influence of mind-altering substances.

Maria Theresa

Voiced by: Kanika Looby

• Sassy Black Woman: And how!
• Jive Turkey: One of the few characters who uses Ebonics frequently throughout the game.

Dr. Bambillo

Voiced by: Brian Doerries

• The Cobbler's Children Have No Shoes: Despite his profession as a psychologist, he has a ton of his own problems: he's very insecure, he's incredibly superstitious, and he's something of a douche.
• Confess in Confidence: He doesn't seem to put much stock in doctor-patient confidentiality. His dialogue on the streets and in conversations reveals much about the students of Bullworth; Gary and Bif are apparently on medication, and Damon is apparently mentally ill.
• Dr. Jerk: He's a doctor, and also one of the haughtiest, most unpleasant residents of Old Bullworth Vale.
• Pet the Dog: For all of his jerkassery he at least cares enough about his dog to pay Jimmy money to find it in a side-mission.

Mr. Breckindale

Voiced by: Unknown

• Flat Character: He's wealthy and brags about it a lot—that's all there is to him.
• Rich Bastard: His only character trait.

Mr. Doolin

Voiced by: Howard Ross

• Con Man: How he earns his living, apparently specializing in real estate and insurance scams.
• Then Let Me Be Evil: He made a fortune entirely as a scammer—as he puts it, everyone else is so corrupt he didn't see any reason why he shouldn't.

Ms. Isaacs

Voiced by: Tiffany Little-Canfield

• Ascended Extra: Well, her character model, not her. Ms. Isaacs was one of the few characters to never have any individual role at any point in the original game. So, in Scholarship Edition, during the mission "Rudy the Red Nosed Santa", all the parents dialogue was assigned to her character model and the model was placed just off camera to give the illusion of multiple characters.
• Pretty in Mink: Her most common outfit is blue coat with a silver fur collar.
• Stepford Smiler: Talks about her wealth and her loves of cashmere and pursuing love itself. Actually an arrogant woman whose previous cheating incident left her no choice but to move to a town she dislikes.
• Unreliable Narrator: She talks a lot about why she left an unspecified Big City to move to Bullworth, and her stories always paint her in the best light - even when they conflict with each other.

Bethany Jones

Voiced by: Lane Keough

• Brainless Beauty: She's a model, but isn't very bright.
• Hypocritical Humor: When arguing with schoolchildren, she makes fun of them for being childish.

Miss Kopke

Voiced by: Kerry Shaw

• The One That Got Away: During a fight, she claims she'll beat the person up as if they were her cheating ex.
• Stepford Smiler: Despite being rather nice from the outside, she suffers from several medical conditions, thinks she needs plastic surgery, and had some form of turbulent relationship in the past. She also cheats on her current husband too.

Mr. Martin

Voiced by: Unknown

• Awful Wedded Life: He's on the outs with his wife, and he's absolutely miserable.
• Like Father, Like Son: He's bitter and angry, and his son Wade is bitter and angry.

Mr. Ramirez

Voiced by: Gregory Johnson

• Gratuitous Spanish: Occasionally adds in Spanish words into his dialogue.
• Happily Married: A real family man in the Dysfunction Junction that is Bullworth.
• Nice Guy: He's one of the most well-adjusted people in Bullworth.
• Token Minority: One of the few explicitly Hispanic characters in the game.

Ms. Rushinski

Voiced by: Franceska Clemens

• Good Is Not Nice: She sacrifices a lot to take care of her kids (or at least claims to), but also brags about it constantly.
• Struggling Single Mother: Talks about being one a lot.

Mr. Smith

Voiced by: Tom Mardirosian

• Big, Screwed-Up Family: If you put the random bits of gossip around town together, his family is this. His son was born into privilege but grew up to be a washout who married a woman of ill repute from New Coventry. It's then implied that they are Gary Smith's parents, which would make Mr. Smith his grandfather.
• Fiction 500: Is rich, even by Bullworth Vale standards.
• Impossibly Tacky Clothes: His garish gold jewellery and Hawaiian shirt, and in wintertime his leather jacket.
• Inadequate Inheritor: Views his son as a poor man to inherit his business, but it's too late to stop him.
• Nouveau Riche: Made his money through his own hard work, unlike a lot of the Bullworth Vale bluebloods.
• Self-Made Man: He, in his own words, "founded... an Empire.
• Sketchy Successor: His son is shaping up to be a terrible disappointment.

Mr. Sullivan

Voiced by: Sanford Santacroce

• Awful Wedded Life: He doesn't get along with his wife and spends most of his time working or running errands to avoid her.
• The Eeyore: Is pretty glum most of the time.
• Good Parents: At least tries to be — he hasn't divorced his wife for his kids' sake and he buys them expensive toys.

Miss Abby

Voiced by: Stephanie Hepburn

• Actual Pacifist: Apparently, she's the only character in the game who will never fight at all.
• Forgetful Jones: Even known to forget her name at times.
• Miniature Senior Citizens: She's stooped with age and about the same height as the average high school kid.

Mr. Buckingham

Voiced by: Michael Bower

• Brilliant, but Lazy: Claims to be "smart and underappreciated" at his job.
• Emasculated Cuckold: He's either married to or dating Miss Kopke (the game itself is inconsistent on which), she's cheating on him, he knows it, and he wants to catch her in the act to shame her in order to downplay this trope - so he hires Jimmy to take pictures.
• The Slacker: Admits to having little respect for his job and regularly half-assing it. Sometimes his boss catches him and makes him redo his work, which he hates.

Mr. Castillo

Voiced by: Marco Rodriguez

• The Alcoholic: Mentions that he spends a lot of time hiding in bars to avoid his wife.
• Awful Wedded Life: Like Mr. Sullivan, he can't stand to be around his wife. At least he doesn't have a kid.

Chuck

Voiced by: Anthony Litton

• Gentle Giant: Despite being a massively muscular construction worker, he likes to wax poetic about the seasons and believes that the biggest problem boys have these days is too much discipline.

Denny

Voiced by: Vincent Lombardi

• The Quiet One: For a weird reason. It seems Denny was programmed as a shopkeeper and then switched to a townsfolk at the last minute—so he has no 'chatter' dialogue and doesn't speak under general circumstances.
• The Quincy Punk: His leather tights, tattoo sleeves, mohawk and tons of piercings fit the aesthetic.

Handy

Voiced by: Paul Diomede

• Jerkass: He constantly insults Jimmy, saying things like "Even I wouldn't want your clothes", "Even my teeth are better than yours", and "I hate you, yes you!".
• Small Name, Big Ego: One of his quotes is "You're not nearly as important as me!". Keep in mind he's a homeless man.

Mr. Johnson

Voiced by: Todd Pistone

• Workaholic: Works all the time, loves it, doesn't understand how anybody can be any other way.

Krakauer

Voiced by: Walter Mueller

• Shell-Shocked Veteran: He fought (or at least thinks he fought) in both World War I and World War II. Supposedly he was an ace pilot, and he complains about such ace pilots as Eddie Rickenbacker and Roy Brown stealing his kills and his glory. But he claims he got demoted to the trenches, and now claims he kills people and buries them in his back yard.

McInnis

Voiced by: Unknown

Mihailovich

Voiced by: Gregory Korostishevsky

• Boomerang Bigot: He despises America and Americans, despite living in America. He's ethnically some unspecified Eastern European.

Osbourne

Voiced by: Unknown

• Jaded Washout: Former star quarterback for the Bullworth Bullhorns, now owns a newspaper stand and his cheerleader wife "couldn't wear her old cheerleading skirt as a garter" according to him.''
• No Name Given: His name was found in the datafiles, never mentioned in the game itself.

Mr. Salvatore

Voiced by Steve Carlesi

• The Casanova: Claims it about himself, no evidence on whether it's true or not.