Original air date: 10/9/1994

Production code: 2F02

With help from the Rush Limbaugh-esque Birch Barlow (a conservative talk radio personality), Sideshow Bob gets released from prison again and runs for mayor against "Diamond" Joe Quimby — and Bart and Lisa investigate how one criminal running for public office got so many votes while another criminal got so few.

This episode contains examples of:

• 0% Approval Rating: Quimby gets a very literal application of this trope, even without taking into account Bob's ballot stuffing.
  Kent Brockman: The results are in: for Sideshow Bob, one hundred percent; and for Joe Quimby, one percent. And, we remind you, there is a one percent margin of error.
• Accidental Misnaming:
  • Jimbo calls Quimby "Grimby."
  • Homer says "Terwigiger" instead of "Terwilliger."
• Accidental Public Confession: Well, not quite accidental: Bart and Lisa get Bob to confess by accusing him of being Barlow's front man. He immediately produces several binders and floppy disks detailing his "masterpiece of electoral fraud".
• Accuse the Witness: When Bart and Lisa discover that Bob won through voter fraud, they don't accuse him outright. Rather, they claim Birch Barlow did it and Bob was just his patsy. This works in their favor, as Bob's bruised ego compels him to confess to his crime and produce massive amounts of evidence proving he committed it.
• Actually Pretty Funny: Bart's opinion of the "Les Wynan" joke.
  Lisa: There's no Councilman Les Wynan.
  Bart: Good line, though.
• Alliterative Name: Robert "Bob" Birch Barlow.
• Ambiguously Gay: This episode marks one of the first times that Smithers is implied to actually be gay, with him going against the Republican party's schemes because their positions "conflict with [his] choice of lifestyle".
• Anything You Can Do, I Can Do Better: When Bob is campaigning at the Springfield Retirement Castle, Grampa Simpson taunts him with the fact that Mayor Quimby already promised to name the town's new expressway after Matlock and dares him to top that. Bob then promises to not only also build the Matlock Expressway if the old folks vote for him, but he'll spend the rest of the afternoon listening to their interminable anecdotes. That wins them over immediately.
• Apologetic Attacker: Bob, outside the Simpsons home with a construction crew:
  So sorry, Mr. Simpson. Your house is blocking construction of our new Matlock Expressway. Now, I am a fair man. You will have 72 hours to vacate. At that time, we will blow up your house and any remaining Simpsons.
• Arch-Enemy: Along with Bob, Bart evidently has one in the form of Dr. Demento.
• Artistic License: The gravestone for Ritchie Valens mistakenly states he was born in 1942. Valens was 17 years old at the time he died, but was actually born in 1941 (he lived from May 13, 1941 to February 3, 1959).
• Artistic License – Politics: The results of the Springfield mayoral election are announced on television in the style of a reality or talent show elimination contest or something like it. In reality, the results would trickle in gradually and (in a contest as lopsided, supposedly, as this one) the winner would be 'called' fairly early on. If the way of declaring the results bares any resemblance to any real-life elections, it would be elections in the UK, in which each individual seat has its results declared at once by a returning officer who reads the results out.
• As Himself: Dr. Demento; Larry King.
• As You Know: Justified; the name "Sideshow Bob" doesn't ring any bells for Homer, compelling Lisa to provide a recap.
  Homer: Oh, SideSHOW Bob.
• Bait-and-Switch: When Bart and Lisa make Quimby look good at the mayor debate at their school, Bob and his aides drag Bart into their limo. Bob angrily threatens Bart that no children have meddled with the Republican party and lived to tell about it, and snaps his fingers. His aides reach into their coats, and Bart's expecting them to pull out weapons...but they pull out some campaign buttons and pin them on his shirt. They then dump him unharmed on the Simpsons' front lawn before driving away.
• Big "NO!": Bart screams "Noooo!!!" when he hears that Birch Barlow wants Sideshow Bob to be set free.
• Biting-the-Hand Humor:
  Larry King: Now, a word to our audience: even though we're being broadcast on... Fox, there's no need for obnoxious hooting and hollering. [The audience does just that; King groans.]
• Black-and-Grey Morality: The race between Quimby and Bob is basically this, paralleling common appraisals of Democrats and Republicans. Quimby is incompetent, stupid, and controlled by his vices, but he's not out to hurt anyone; he just wants to keep Springfield running. Bob, on the other hand, is a psychotic megalomaniac who wants to rule like a king and kill anyone he has a grudge on.
• Bread, Eggs, Milk, Squick: Mayor Quimby's campaign jingle includes a list of Quimby's "achievements":
  Without a Mayor Quimby, our town would really stink.
  We wouldn't have a tire yard, or a mid-sized roller rink.
  We wouldn't have our gallows, or our shiny Bigfoot trap.
  It's not the mayor's fault that the stadium collapsed!
  • At the end, Bob states that Springfield residents secretly want a Republican mayor to "lower taxes, brutalize criminals, and rule you like a king".
• Brick Joke:
  • The bats in the public library.
  • Homer gets thrown out of Riverdale for reasons unknown (or do we want to know). When he drives Bart and Lisa to meet the unknown informant in the parking garage, Homer stays in the car, reading Archie Comics, muttering, "Lousy stuck-up Riverdale punks! Think they're too good for me."
• By the Lights of Their Eyes: In the Couch Gag for this episode (recycled from "Boy Scoutz 'n the Hood"), the lights are out with only the Simpsons' eyes visible as they enter. The lights turn on revealing it's only their eyes, until the family rushes in and sits down, reconnecting with their eyes.
• Caligula's Horse: Most of the Springfield Republican Party mistakenly assume the mayoral candidate they've chosen to back was a water cooler. They seemed to think it would make a fine representative.
• Call-Back: Sideshow Bob exits the Springfield prison in the exact same manner as he did in "Cape Feare," only this time plummeting off the edge of the island.
  Guard: Boat's on the other side!
• The Cameo: Archie and his pals Jughead, Reggie, and Moose from the Archie comics make a cameo, throwing Homer from their vehicle and telling him to "Stay outta' Riverdale!"
• Cardboard Prison: The fact that the Springfield prison system is made of them is highlighted by Bob in an Attack of the Political Ad (even pointing out that Quimby released him). The ad still manages to take it up to eleven by showing a prison full of methods for quick getaways, from a revolving door up to a ski lift that takes prisoners over the perimeter wall and lets them drop safely on the other side. Though given the minimum security prison Bob is placed in at the end, with no guards in sight and the gate left wide open (which Bob is somehow unable to escape from), this may not be an exaggeration.
• Card-Carrying Villain: The Springfield Republican Party appears with a Dracula/Frankenstein-style Supervillain Lair castle and cult-like procedures headed up by Mr. Burns. Bob's grand speech at the end even makes it clear that the whole In-Universe party and everybody that supports it are a bunch of megalomaniacs that want to rule with an iron fist and idiots that think they would have Happiness in Slavery.
• Car Radio Dispute: Lisa argues with Homer when he tunes his car radio to a Rush Limbaugh expy.
  Lisa: Dad, I had to listen to this jerk all morning! Can we listen to something else?
  Homer: When I'm driving the car, I get to choose the radio station. When you're driving, we'll listen to your radio station.
  (Gilligan Cut to 8-year-old Lisa driving the car, with the radio playing "St. Elmo's Fire" by John Parr)
  Homer: Ooh, I can't take this anymore! Let's switch back!
• Cassandra Truth: invokedBart telling Marge that he was told to bring in fireworks.^note Given Bart's history, one would think Skinner would personally tell Homer and Marge about the project.
• Caught by Arrogance: This is how Sideshow Bob's plot of rigging the mayoral election is revealed. Enraged at being accused of being only a puppet and Birch Barlow of being The Man Behind the Man, Bob flaunts in open court how the scheme was all his idea and his alone. Naturally, this gets him arrested.
• Celebrity Paradox: Archie and the Riverdale gang apparently exist in The Simpsons universe. And yet, while Lisa and Bart do some investigating, Homer is waiting in the car reading an Archie comic.
• Chekhov's Gag:
  • The Matlock Expressway, which Quimby promised to the old people to get their vote. Bob decides to actually build it, on top of the Simpson residence.
  • The ongoing references to Smithers being gay end up being a critical plot point, as he asserts that he would never operate secretly against Mr. Burns if Sideshow Bob's ultraconservative platform weren't in conflict with his "choice of lifestyle." Armed with the tip he gives them, Lisa and Bart blow up the whole scheme.
• Comically Missing the Point: Smithers gives Bart and Lisa a name, and Bart finally finds its owner—in a cemetery plot. His takeaway is not the same as Lisa's.
  Bart: Oh my God! The dead have risen and they're voting Republican!
• The Comically Serious: Bart.
  Lisa: Bart, we can't let Bob steal the spotlight like this. I'm afraid we're going to have to stoop to the Lowest Common Denominator.
  Bart: I can do that.
• Comic Books Are Real: A rare non-Superhero example. Homer reads Archie Comics, while in the same episode, he is kicked out of Riverdale by Archie and his friends.
• Comic-Book Time: Lisa specifically mentions that Sideshow Bob framed Krusty for armed robbery in "1990," the year "Krusty Gets Busted" came out, four years before the release of this episode.
• Continuity Nod: Lisa reminds Homer of Bob framing Krusty for robbery and his more recent attempts to kill Selma and Bart.
• Creator Cameo: A caricature of Simpsons producer Richard Sakai can be seen in the pro-Sideshow Bob ad.
• Crowning the Criminal: Subverted and Parodied. Sideshow Bob manages to easily beat Quimby in the Mayoral Election in spite of his open criminal platform and noted history (he even lists he wants to kill Bart and Selma as part of his policy, but Homer and Krusty both vote for him due to the latter policy and a promised upper class tax break), but it turns out that Bob rigged the election.
• Department of Redundancy Department: "Quimby: If you were voting for mayor, he'd vote for you. (Paid for by the Mayor Quimby for Mayor Mayoral Committee.)"
• Devil in Plain Sight: The reaction to Bob's below-mentioned evil laugh? "And just look how happy he is!" If you hear well, it sounds like everyone is laughing with him.
• Devilish Hair Horns: Quimby inadvertently sports hair horns during the mayoral debates after he runs his fingers through his sweat-soaked hair, leading the news team to electronically demonize him in their broadcast.
• Dick Dastardly Stops to Cheat: Bob goes for ballot-stuffing in an election where Quimby may have actually had a 0% Approval Rating. Several elements of his platform also legitimately appealed to various voters, like Homer approving of his "Selma-killing policy" and Krusty liking Bob's proposed upper-class tax cut. Justified, as he didn't know how guaranteed the race was, and his rant at the end shows he didn't expect Springfield to vote Republican even if they secretly wanted to.
• Election Day Episode: This episode revolves around the Springfield mayoral election.
• Engineered Public Confession: Once Bart and Lisa have proof Bob stole the election, they bring him to court and get this out of him via reverse-Appeal to Flattery.
• Evil Is Petty: As soon as he is elected, Bob uses his power to make the Simpsons as miserable as possible, planning to mow down their house to make room for the new Matlock Expressway and sending Bart to kindergarten (being a class flunky, however, he only ends up enjoying this). He also has plans to kill Bart and Selma that he included in his political platform.
• Evil Laugh: Sideshow Bob, of course, delivers a long, utterly hammy one after he wins the election.
• Explosive Stupidity: After misunderstanding a report of Sideshow Bob being a political prisoner and being told to "do whatever it takes to get him out of jail", Moe hands out a grenade to each of his barflies. When Barney corrects him that they meant "through non-violent grassroots political action", Moe takes the grenades back, only to find out that somebody pulled the pin on their grenade almost the second they were given it.
• Expy Coexistence: Birch Barlow mentions “cartoon smokesperson” Joe Camel; Laramie Cigarettes has been shown to have its own mascot, Menthol Moose.
• Failed Attempt at Drama: Bob's Cape Fear (1991)-style menacing exit from prison is ruined by him not noticing that he was walking towards the camera but also right towards the edge of a cliff.
• Fair-Weather Friend: Except for the Simpsons, everyone with Quimby at his campaign headquarters leaves as soon as Sideshow Bob is announced as the new mayor.
• Falsely Reformed Villain: Sideshow Bob pretends to go straight so he can get paroled out of prison and rig the election campaign for mayor.
• Flaw Exploitation: Bart and Lisa falsely accuse Birch Barlow of being the mastermind behind the electoral fraud, knowing that Bob's pride won't allow him to stand for being called a mere pawn in someone else's scheme.
• Friend to Psychos: While he's plenty psycho himself, Mr. Burns lends some respectability to Bob by endorsing his campaign. Birch Barlow is a better example, since he really is a fool and has no idea what he's getting into.
• Gilligan Cut: Lisa asks Homer if they can listen to something else. He replies that, as the driver, he chooses the radio station. When she drives, then she can choose the station. Cut to Lisa driving and listening to "St. Elmo's Fire (Man in Motion)".
  Homer: Ooooh. I can't take it anymore! Let's switch back!
• Grave Humor: The inscription on The Big Bopper's tombstone: "GOOD-BYYYYYYE, BABY!"
• Hammerspace Hair: Where Sideshow Bob keeps his multivolume records of voter fraud, hardcopies in three-ring binders, digital copies on 3.25" floppy disks.
• Handwave: Lisa can have the results of the votes and the voters' identity because no one cares. This is vital to find out Bob stuffed the ballots with dead people.
• Heteronormative Crusader: After Smithers is revealed to be the Deep Throat-esque Mysterious Informant who starts Bart and Lisa's path to revealing Bob's fraud, he gives a speech that heavily implies that Bob is one of these, so he's helping the kids to prevent whatever punitive measures Bob may bring to the Springfield gay population (and Smithers in specific).
• Hidden Depths: Barney Gumble, of all people, is the one who points out to Moe that Bob meant "take political action" and not "grenade-tossing rebellion" when he asked for people to help him get out of jail.
• Hold the Line: While Bart and Lisa dig up evidence and take Bob to court, Homer and Marge keep the construction crew from demolishing their house; Homer by using his own body to soften the wrecking ball's swings and Marge warding off the workers with promises of rolling pin attacks.
• Homage: The entire second act, including the bird's-eye shot of Lisa studying in the library, is an homage to All the President's Men.
• Hypocrite Has a Point: Bob's political attack ad reams Quimby out for releasing dangerous criminals from prison like Sideshow Bob. He's not wrong, considering how Bob immediately capitalized on it to run for mayor to try and kill Bart for the umpteenth time.
• Hypocritical Humor:
  • The ad Bob created to attack Quimby accuses him of letting criminals easily walk free.
    Announcer: Mayor Quimby supports revolving door prisons. Mayor Quimby even released Sideshow Bob, a man twice convicted of attempted murder. Can you trust a man like Mayor Quimby? [Hushed and rushed] Vote Sideshow Bob for mayor!
  • Also, Homer had earlier in the episode stated a low opinion about people who vote, but he's later seen voting for Sideshow Bob. (He approved Bob's "Selma-killing policy".)
  • At the end, Bob states that Springfield residents secretly want a Republican mayor to "brutalize criminals", despite being a criminal himself (of course, Bob doesn't believe "attempted murder" is actually a crime, but he did commit electoral fraud—another crime).
• I Approved This Message: The Image Source for this trope is in this episode.
• Immediate Self-Contradiction: Describing the perfect mayoral candidate for the Republican Party, Burns states they need someone with media savvy and name recognition, "a true leader, who'll do exactly as he's told."
• Insane Troll Logic: Sideshow Bob runs on this, as seen in his aforementioned campaign ad.
  Sideshow Bob: ...I'm presently incarcerated. Convicted of a crime I didn't even commit. "Attempted murder", now honestly, what is that? Do they give a Nobel Prize for "attempted chemistry"?
• Instantly Proven Wrong: When Bob tells the Simpsons their house will be demolished to clear the path of the freeway.
  Homer: I know what you're up to, Mayor Terwigager. And no one in my family's gonna stand for it!
  Abe: (honking his car horn from the top of the unfinished construction) Move your goddurn house, son!
• Intellectually Supported Tyranny: Bob uses this to justify his corruption as part of his Motive Rant. He claims that Springfielders' guilty consciences "force" them to vote Democratic, but that they secretly want a cold-hearted Republican to lower taxes, brutalize criminals, and rule them like a king. He said he manipulated his way into the Mayor's chair to "save you from yourselves!" It doesn't really help, since the judge immediately orders Bob's arrest.
• Invented Individual: During the mayoral debate, Barlow asks Sideshow Bob what he thinks of a criticism leveled at his campaign by "Councilman Les Wynan," to which Bob responds that the councilman "ought to do more thinking and less whinin'." As no one but Lisa realizes, there's no such person as Les Wynan and the name was just invented to set Bob up for the line.
• I Take Offense to That Last One:
  Birch Barlow: There are three things we are never going to get rid of in this town. One, the bats in the public library; two, Mrs. McFuly's compost heap; and three, our six-term mayor — the illiterate, tax-cheating, wife-swapping, pot-smoking spendocrat, "Diamond" Joe Quimby.
  Mayor Quimby: [as he's watering a marijuana plant in his office] Hey! I am no longer illiterate!
• It's Personal: Lisa states this after finding out one of the dead people and pets that "voted" for Bob was her long-deceased cat, Snowball I. Bart, understandably, takes offense at this:
  Bart: Um... he did try to kill me.
• Kevlard: Homer grabs onto the wrecking ball to stop it from tearing down the Simpsons' house. The MythCrackers showed that his heft actually protected the house in this instance.
• Kids Driving Cars: Apparently Homer regularly lets his children take turns driving the car so they can pick the music.
• Landslide Election: Exaggerated. Bob wins the mayoralty by a margin of at least 99 percentage points (with Quimby possibly not getting any votes, taking into account the 1% margin-of-error), but Quimby is reinstated when Lisa and Bart expose Bob's cheating.
• Laser-Guided Karma:
  • Barlow's is having Bart and Lisa accuse him of being The Man Behind the Man for Bob's electoral fraud.
  • Bob is arrested immediately after revealing he's been massively corrupt.
    Judge: Bailiffs, place the mayor under arrest.
    Sideshow Bob: WHAT?! Oh yes, all that stuff I did.
• Laughing Mad:
  • Bob, after being elected mayor.
    Kent Brockman: And look how happy he is!
  • Mrs. McFuly has a pretty deranged cackle as well.
• Lawyer-Friendly Cameo: The bit where Homer is thrown out of Riverdale by the Archie Comics gang was intended to be one these, but Archie's lawyers complained anyway and the episode's credits specifically mention the publisher.
• Lesser of Two Evils: Mayor Quimby is outright stated to be this by the Simpson children, as they believe Bob would really spell disaster as mayor (and then proved right when he wins).
• Lesser Star: Bart and Lisa invoke this in their plan to get Sideshow Bob to confess to rigging the mayoral election, by accusing him of playing second-fiddle to Limbaugh expy Birch Barlow.
  Bart: You were just Barlow's lackey!
  Lisa: You were Ronnie to his Nancy!
  Bart: Sonny to his Cher!
  Lisa: Ringo to his rest of The Beatles!
• Lighter and Softer: Subverted. Although Bob doesn't try to murder anyone onscreen (and children who meddle with the Republican Party get the Faux Horrific fate of having Republican buttons pinned onto their clothes and unceremoniously sent home), he openly advocates killing both Bart Simpson and Selma Bouvier in his platform, and warns the Simpsons that if they don't vacate their house within 24 hours, he will blow it up along with any remaining family members.
• A Lighter Shade of Black: Quimby is a Sleazy and Corrupt Politician, but at least he isn't making it his mission to destroy the Simpsons' lives like Bob is, which is why Lisa and Bart campaign for him. It's also why people like Homer and Krusty vote for Bob, even though they both have reason to loathe him.
• Made of Iron: Homer can somehow cushion a wrecking ball from hitting his house and doesn't even flinch.
• The Man Behind the Man: Played with when Bart and Lisa shift the accusation of the rigged election to Birch Barlow to get Sideshow Bob to confess.
• Match Cut: Homer says that something about Birch Barlow really speaks to him. Cut (actually a very quick fade) to Birch sitting in Homer's exact same pose, eating Homer's exact same doughnuts.
• Mayor Pain: The whole episode is a battle between the evil variety and the incompetent variety.
• Meaningful Name: "Birch" is likely meant to be a reference to the infamous John Birch Society, a radical conservative/Conspiracy Theorist group formed during the 1950s.
• Might as Well Not Be in Prison at All: The minimum-security prison that Bob is sentenced to features canoe races between Yale and Princeton alumni. That, and a gate left wide open.
• My Friends... and Zoidberg: Bob addresses the Springfield students as "children," singles out Bart, then ignores him to continue talking to his "young friends."
• Mysterious Informant: Parodied; the informant of this type Bart and Lisa meet in a parking garage is blatantly Waylon Smithers, even as he stands in the shadows wearing a trenchcoat and smoking a cigarette (his distinct hairstyle is clearly noticeable, along with slightly disguising his voice)... and well before Homer confirms this by shining his car headlights on Smithers.
• Never My Fault: Bob is introduced in this episode complaining about being imprisoned for attempted murder, specifically saying that he's falsely imprisoned for a crime he didn't commit.
• Nice Job Breaking It, Hero!: Quimby has flu at the time of the debate, so Bart gives him medicine — specifically, extra-drowsy medicine, which just impairs his performance even more.
• The Nicknamer: Birch Barlow makes pejorative nicknames for anything remotely liberal, using alliterations and portmanteaus.
• No Celebrities Were Harmed: As noted, Birch Barlow is one of real-life conservative radio personality Rush Limbaugh.
• Non-Standard Character Design: Archie and his friends are drawn in their own style when they make their cameo.
• Noodle Incident:
  • What did Homer do to get thrown out of Riverdale? Better yet, how'd he get there in the first place?
  • And what did Bart do to gain the enmity of Doctor Demento?
  • The collapsed stadium. All we know is that it supposedly wasn't Quimby's fault.
• Not Hyperbole: When Birch Barlow says Springfield will never get rid of Mrs. McFuly's large, disgusting compost heap, he's not just exaggerating. She guards it madly with a shotgun.
• Obnoxious In-Laws: Maybe Homer has other reasons to vote for Bob, but the one that we hear him approve of out loud is Bob's campaign promise to kill his sister-in-law Selma if he's elected.
• Only in It for the Money: Krusty hasn't forgotten Bob framing him for armed robbery, but he votes for Bob anyway because he really likes Bob's proposed upper-class tax cut.
• OOC Is Serious Business: Smithers gives Lisa and Bart a tip, claiming he's never gone behind Burns' back before but that "Sideshow Bob's ultraconservative views conflict with my... choice of lifestyle."
• Open Secret: Apparently who you voted for mayor is not anonymously done and everyone can learn it.
• Paper Tiger: Barlow, essentially. Although he's got a devoted following amongst his radio listeners, is an influence to the Republican Party and is able to get the best of a long-term incumbent mayor in a debate, when he's called out on his involvement in the rigging of the mayoral race by a child (something that can and will have him incarcerated), he turns into a flustered, barely coherent mess.
• Parking Garage: Parodied when Bart and Lisa go to meet an informant (who turns out to be Mr. Smithers) in a garage. He goes to great lengths to conceal his identity (wearing a trench coat, smoking, standing in the shadows, etc.) but the effect is ruined when Homer drives up, turns on his headlights, and loudly greets him.
  Smithers: [Annoyed] Well, you might as well give me a ride home now...
• Parody Assistance: Bart plays with a Flintstones toy phone, which features Henry Corden as the voice of Fred Flintstone.
• Paste Eater: When Quimby and Bob come to Springfield Elementary:
  Skinner: Now, students, I want you to be on your best behavior for this carefully-choreographed media event. Now this means there is to be no wising-off, no face-making, and no grass-eating. This means you, Ralph.
  Ralph: [Mouth full of grass] Yes, sir.
• Pompous Political Pundit: Birch Barlow is a caricature of Rush Limbaugh that labels Quimby as one of the biggest obstacles in the improvement of Springfield as a city (he's right, of course, but his delivery is as ham-fisted an Attack of the Political Ad as it gets) to the point he endorses and helps a convicted criminal, and when it comes to asking on debate night, well:
  Birch Barlow: Mayor Quimby, you are well known, sir, for your lenient stance on crime. But suppose for a second that your house was ransacked by thugs, your family tied up in the basement, with socks in their mouths, you try to open the door but there's too much blood on the knob—
  Mayor Quimby: What is your ah, question?
  Birch Barlow: My question's about the budget, sir.
• Pride Makes You Dumb: Bob commits voter fraud to ensure that his campaign to become mayor of Springfield succeeds. Bart and Lisa don't have evidence to prove it, so they decide to goad Bob into exposing himself by suggesting that Bob isn't smart enough to pull off the scheme himself and that he was just a patsy to Birch Barlow. Bob, being too egotistical to just go along with the accusation, decides to not only confess to his crime but also gives proof in order to show that it was definitively his scheme. As a result, he gets arrested despite having won the election because he needed to prove his genius.
• Railroad Plot: Deliberately created by Sideshow Bob to harass the Simpsons when he directs the construction of a new freeway right toward their house.
• Rambling Old Man Monologue: To secure the senior voters, Bob promises that, besides building the expressway, he'll patiently spend the entire afternoon listening to the residents in the Springfield Retirement Castle. Abe goes ahead and call dibs to start.
  Abe: Not many people know, I owned one of the first radios in Springfield. T'weren't much on the air then, just Edison repeating the alphabet oooover and oooover. "A", he'd say. Then "B". "C" would usually follow...
  Bob: [annoyed grumble]
• Reality Is Unrealistic: As it turns out, graveyard votes, votes cast by people who are deceased, is a common form of fraud still used today.
• Riddle for the Ages:
  • What was Homer doing in Riverdale, and how did he get kicked out of there?
  • Why did the stadium collapse?
• Rigged Contest: The mayoral debates have Barlow giving Bob easy questions from a nonexistent "Les Wynan", and Quimby a rambling, disturbing question about his family being kidnapped and murdered by thugs that's somehow about the budget.
• Shout-Out:
  • Politicians using the votes of people who passed away happened earlier in American history.
  • Quimby and Sideshow Bob's TV debate is a reference to John F. Kennedy and Richard Nixon's 1960 TV debate.
  • The "about the budget" question appears to be a reference to the 1988 presidential debate, where Bernard Shaw asked Michael Dukakis if he—hypothetically—would still refuse to support the death penalty for a criminal that had murdered and raped his wife.
  • Sideshow Bob posing in front of his election poster references Citizen Kane.
  • The entire second act is a parody of the Watergate scandal, specifically spoofing its depiction in All the President's Men.
  • The commercial described in Hypocritical Humor is a parody of the infamous "Willie Horton" advertisement by the George H. W. Bush campaign during the 1988 presidential race.
  • The episode's title is a reference to the satirical political mockumentary Bob Roberts.
  • Sideshow Bob tries to demolish the Simpson family home to make way for a bypass. Why does that sound familiar?
  • There are a number of striking parallels to the "Penguin-for-Mayor" main plot of Tim Burton's Batman Returns: a killer runs for municipal office despite having no previous political experience and does surprisingly well; the incumbent mayor is (hypocritically) accused of being soft on crime; research is conducted at the Hall of Records; and the mastermind behind the campaign is an energy-sector tycoon who is sabotaged by a seemingly mousy underling.
• Single-Target Sexuality: Subverted. Smithers alludes to being gay when, in previous episodes, it was heavily implied that he was either sexually confused or straight, but had a crush on his boss.
• Skewed Priorities:
  • Homer votes for Bob because he promises to kill Selma despite also wanting to kill Bart.
  • Krusty votes for Bob for the tax cuts for the upper class despite Bob framing him for armed robbery.
  • Lisa declares that It's Personal after Bob used her dead cat as one of the fraudulent votes. Bart indignantly reminds her that Bob tried to kill him.
• Special Guest: Henry Corden as Fred Flintstone;^note The voice on the Flintstone phone. Kelsey Grammer (a registered Republican in real life) as Sideshow Bob; Phil Hartman as Lionel Hutz.
• Stealth Pun: In the scene where Homer argues with Lisa about radio channels, their dominant hands are different — right and left, respectively. (They're in the driver's and shotgun seat of an American car, respectively.)
• Still Got It: When Springfield Elementary School hosts a candidates' debate, Bob shows that he's still got the skills he used as Krusty's sidekick. He wows both the children and the media with everything from goofy walking to tumbling to juggling to folding himself down to less than half his height.
• Strange Minds Think Alike: Homer starts to listen to Barlow's broadcasts because he feels a kind of kindred spirit connection with Barlow. Just as he says this, we cut to Barlow inside of the recording booth and he's gobbling down on donuts in a similar fashion to Homer.
• Suspiciously Specific Denial: A TV ad for Quimby ends with: "It's not the mayor's fault that the stadium collapsed!"
• Take That!:
  • This is the first time the show really takes stabs at the Republican Party, which garnered a lot of complaints from viewers (particularly the ones on snpp.com who were used to seeing the show skewer both political parties (or only focus on local politics and not national stuff). Of course, considering that Mayor Quimby is the episode's representative of the Democratic Party, it does even out somewhat.
  • Of course, even though the episode was meant to spoof both Democrats and Republicans (but especially Republicans, as Matt Groening is a left-leaning Democrat), he revealed this episode attracted many right-wingers who invited him to join their political groups/organizations.invoked
  • Also, disappointment was expressed in the DVD Commentaryinvoked of the episode that Lisa would listen to "St. Elmo's Fire (Man in Motion)".
  • Apparently, Mayor Quimby got sick right before the debate due to shaking hands with old people.
• The Television Talks Back: More like "The Radio Says 'Ow' When You Throw It Through A Glass Window", but that's too specific.
• Tempting Fate: Just before the disastrous debate, Lisa wonders if Quimby's flu will effect his performance. Bart assures her that he'll be fine, having taken dozens of anti-flu capsules. Then he sees they're an "extra-drowsy" formula.
• This Is Gonna Suck: Bob reacts this way when Grampa starts the first of the many Rambling Old Man Monologues he'll have to listen to for the rest of the afternoon.
• This Loser Is You: Among the voters who pull the lever for Bob in the mayoral election are Homer (whose son Bob has tried to kill several times) and Krusty the Klown (who Bob framed for armed robbery and sent to prison), because they are in favor of Bob's "Selma-killing policy" and an upper-class tax cut, respectively.
• Title-Only Opening: The second FOX airing and the DVD version goes from the Simpsons cloud title straight to the executive credits on the TV, while the original airing and the syndicated version had couch gags that were used in other episodes (the original airing had the couch gag from "Boy Scoutz 'n the Hood"^note The Simpsons' eyes are floating in the dark. while the syndicated version had the oft-used one from "Rosebud"^note The Simpsons run in and find identical versions of themselves on the couch.). This is one of the few times they did this after season one and before the high-def episodes from season 20 on (barring the special episodes, like the Treehouse of Horror episodes and the two Troy McClure-hosted episodes: "The Simpsons 138th Episode Spectacular" and "The Simpsons Spinoff Showcase").
• Ungrateful Bastard: After being pardoned by Mayor Quimby, Bob not only runs against him for the opposing party, but runs a rather nasty (read: slanderous) attack ad claiming Quimby was soft on crime, seeing as he had pardoned a convict who was twice convicted of attempted murder — Bob himself. Bob won the election after rigging the votes, even though he would have won legally since he apparently got 100% (or some figure traditionally rounded up to 100%) of the vote.
• Unishment: Bob uses his power as mayor to get Bart sent back to kindergarten. Bart loves it: he's finally acing a class and he gets to play with kid's toys ("I call the Flintstone phone!")
• Varying Competency Alibi: Sideshow Bob is on trial for committing electoral fraud to get himself elected mayor of Springfield. Bart and Lisa accuse Bob of not being the real mastermind behind the fraud, pinning it instead on Pompous Political Pundit Birch Barlow, with Bob being little more than Barlow's lackey. This, of course, was just a ruse to get Bob to confess, as his ego wouldn't allow him to be seen as incompetent.
• Villain Decay: Whereas Sideshow Bob was striving to enact a mortal grudge against Bart in his last appearance and attempting murder even before that, here he's just trying to make life as annoying for the Simpsons as possible. Compare their highest personal stake—the possibility that they could lose their home—to the fact that last time around they themselves opted to leave town and adopt new identities just to get Bart off his radar. There is a gag about killing Bart and Selma being part of his platform, but the worst he does to either of them personally is get Bart bumped down to kindergarten. Which he enjoys.
• Villain Has a Point: Birch Barlow's not wrong that Quimby is extremely corrupt, but he blames his long reign in Springfield on "tie-dyed tree huggers who would rather play hacky sack than lock up the homeless."
• Vote Early, Vote Often: Sideshow Bob's victory in the election is swiftly undone when he's revealed to have rigged it even though he probably would've won legitimately.
• Where the Hell Is Springfield?: Buddy Holly, Ritchie Valens, and The Big Bopper, who were all killed on "The Day The Music Died", are among the dead people who allegedly voted for Sideshow Bob. Holly and the Big Bopper were both buried in Texas, and Valens was buried in California, neither of which borders one another.
• Worf Had the Flu: A literal example in that Mayor Quimby's really sick after having shaken hands with a bunch of old people. Bob easily demolishes him in the televised debate.
• You Can't Handle the Parody: "...No truth handler, you! Bah, I deride your truth-handling abilities!"