Protagonists

Jair

• Armor Is Useless: The game and instruction manual gives a few references to your hero's armor... and you can get a spiffy new helmet and gauntlets from the castle. But everything still kills you. You should have been a purple-underwear-clad nudie like Ace Harding in the beginning of Deja Vu II. This is rather egregious in the 2014 remake, as you can find various equipment to wear, but all of it protects you from absolutely jack squat^note They make a good disguise for the goblins, though. Averted with the shield you find in the same room as the helmet, as you need it to survive the dragon's flame in the same room. It will still melt and kill you after a certain number of hits though.
• Awesome, but Impractical: The "Hit" command shows a screen-filling, dramatic "POW!"... but it is almost completely worthless except for two very specific occasions (entering the arrow room, and accessing the gem bag). Using it on enemies will result in Jair's immediate death in nearly all cases. Even the Sword is only useful on exactly one enemy, and you have to knock it unconscious with the Sling first for it to work.
• Death by Falling Over: Out of all the possible ways to die in the game, you can also die by simply tripping in the darkness and falling face first if your last torch gets snuffed out. The remake takes it a step further by describing that you fall so hard that blood and grey matter go flying everywhere; hilariously, if you die this way by moving back a room (or turning around) the narration describes how Jair quickly and dramatically whips around before tripping and becoming one with the floor.
• Death by Materialism: If Jair takes the Pot of Gold, he'll fall for the oldest trick in the book and die, he doesn't even need it.
• Epic Fail: Somehow, Jair swings and misses Yorick if he attempts to use the dirk on him:
  You swing... and miss! You wonder how you could've missed the easy target so badly. Yorick just laughs and and guffaws in amusement.
• Good Old Fisticuffs: They are WORTHLESS in the original game as anyone Jair hits will turn him into meatsauce. In the remake, however, they are useful in taking out those pesky goblins. Sometimes.
• Have a Nice Death: The descriptions are varied, and can get fairly graphic. The remake even takes this to a new level with "hidden deaths": a narrator describes Jair's death, accompanying it with visuals and gruesome sounds.
• Heroic Mime:
  • Inverted in the original versions. The hero actually seems to be perfectly capable of speech; it just so happens that no-one in Castle Shadowgate can actually understand what you're saying. Weirdly, this includes the sphinx (who speaks to you during the course of the game) and the Big Bad. The only person who can understand you is the troll, and even then he just says that he doesn't feel like speaking and tells you to get lost.
  • Partially averted in the remake. Jair never speaks in any cutscene, save for screaming for help when he's about to die. Doing certain actions, such as speaking to mirrors, has him give some rather humorous dialogue, usually with Yorick chiming in.
• Kleptomaniac Hero: Jair can take basically anything that isn't nailed down or directly harmful. Of course, like everything else in this game, that too can get him killed.
• Luckily, My Shield Will Protect Me: In the original and remake, the shield will protect him from a few distant licks of a dragon's flame. It is just a useless hunk of metal otherwise in the original. The remake gives a few more useful uses for your shield.
• Made of Plasticine: That'd be him. Some of the death quotes describe this, having him get torn apart by the various horrors, including one here he gets pureed by gargoyles to the point where "there is not enough left of you to feed the birds".
• Magic Knight: Of sorts. Jair is made out to be a fairly decent warrior, it's just that Shadowgate's dangers far surpass his capability, and he does happen to learn magic spells over the course of his adventure, though they're all utility spells meant for solving puzzles rather than attacking his enemies directly.
• Too Dumb to Live: There are a couple cases where Jair is dumb of his own volition:
  • The player telling him to go down a well results in him diving head first — even if the rope is lowered for you to climb down!^note You can climb down it in the remake, fortunately.
  • At another point in the game, Jair can jump into the lava surrounding a platform. Despite the game explicitly telling you that swimming in them would not be wise, Jair is free to jump into them, which, as expected, kills him. The game then promptly tells you "You are brave, warrior, but stupid!!".
  • It is also possible for Jair to keep using a torch on himself (and incurring burns of increasing severity) until he finally catches on fire and dies.
• Violation of Common Sense: He can USE the sword or the spear on himself... Which results in the hero killing himself. Goodness knows why he would want to do that^note some players might think using a weapon on yourself will have you equip it or ready it for combat, but you can do it.
• Violence Is the Only Option: Hey look, a Damsel in Distress chained up in a tower! Let's kill her! Good thing she turned out to be a werewolf, which you didn't know until after the fact! (or you tried something else and got killed). In fairness, almost everything else in Castle Shadowgate tries to kill you, so by this point, the hero probably can't be blamed for shooting first and asking questions later.
• Weapon Twirling: In most cases when using a weapon on himself, you just plain stab yourself. However, with the axe, he tries to do some cool axe moves, but fail and somehow chop himself in half.
• With This Herring: He enters Castle Shadowgate with merely a single torch and worthless armor. The remake is a little more generous giving him a dirk, which is WORTHLESS as weapon, but makes a decent tool.

Princess

• Pimped-Out Dress: The princess is wearing one at the end of the first game, in the versions she appears. The NES version has her in a white dress, possibly with white fur trim (the bitmap image◊ leave it up in the air).

Antagonists

Warlock Lord

• Big Bad: The Warlock Lord intends to cover the world in darkness and you have to stop him at the end.
• Hoist by His Own Petard: The Warlock Lord is defeated when the Hero uses the Staff of Ages on the Behemoth he has just summoned up, and the Behemoth drags the Lord back down into the abyss with him.

Behemoth

• Expy: The remake has the Behemoth as a stone-and-lava creature who has existed since the foundations of the world were laid, much like the Balrog.

Werewolf

• Adaptational Badass: The werewolf in the remake is no longer an apparent Damsel in Distress chained to a wall, but now one of the Warlock Lord's lieutenants. Even gets named (Malor Kalu). Her still trying to kill you is a lot more justified this time around.
• Damsel in Distress: Subverted. The chained woman in the tower is actually a werewolf put there to guard the Golden Blade.
• Named by the Adaptation: In the remake, she's named Malor Kalu.