Tropes:
- Affably Evil: Dracula is a typical parent, despite the whole bloodsucking thing. He embarrasses Edmund while meeting Lisa's parents, and helps Homer chase down the kids when they run away.
- All Just a Bath Time Daydream: "Master and Cadaver" is revealed to be a daydream in Maggie's imagination.
- Asleep for Days: In "Master and Cadaver", Roger said that his boss and his partners were poisoned, just days prior to being rescued by Marge and Homer. However, they were vaccinated from the poison and just laid there for days until they were conveniently woken up by Homer murdering Roger.
- Breaking the Fourth Wall: From "Master and Cadaver", when Homer becomes suspicious of Roger's story and baking prowess.Homer: They should've called this one, "Recipe for Murder".
Marge: What do you mean, "this one"? - Continuity Nod: One of the board games is Ravenous Ravenous Rhinos from "Fat Man and Little Boy".
- Crazy Jealous Guy: Homer in "Master and Cadaver."
- Crazy-Prepared: Roger's boss gave everyone an antidote because he knew their host would try to poison them. This allows them to at least survive up until Homer decides to Leave No Witnesses.Homer: Looks like you've got a flare for avoiding death.
- Demoted to Extra: Kang makes an obligatory brief cameo with no lines as Selma's future hubby in a dating board game.
- Dracula: He is Edmund's father.
- Downer Ending:
- "War and Pieces" ends with Bart defeating the enchanted board-game, only to summon up a live version of hangman. Millhouse fails to guess the last letter, and both boys are hanged.
- In "Master and Cadaver," Marge and Homer learned that they tried to murder an innocent man, only for Homer to murder Roger and all of the people on the ship who were miraculously not poisoned because he wants to leave no witnesses. Marge can't bear the guilt and eats the poisoned pie, leaving Homer alone in a boat full of corpses.
- It's Played for Laughs, but "Tweenlight" concludes with Homer's Heroic Sacrifice below being for naught, when he plummets to his apparent death after transforming into a heavy bat.
- Driven to Suicide:
- After fast forwarding the special at the beginning and thus ruining it for the viewers, Professor Frink fast forwards himself to death.
- Milhouse allows himself to sink into the ocean during "Battle Boat" because he was, in his words, tired of living. He's inexplicably fine again by the hangman game.
- Unable to live with her guilt for the deaths of the innocent people in "Master and Cadaver", Marge eats a poisoned pie.
- Epic Fail: Homer protecting Lisa from getting turned into a vampire in "Tweenlight" is negated due to the fact that he is turned into one instead and when deciding to fly away after turning into a bat he instead plummets to his death due to being too heavy.
- Everyone Has Standards: Lisa was excited at the thought of being a vampire, until she learns that it would make her eight years old forever. Dracula and Edmund still won't let her back out of it though!
- Fanservice: Marge in a black bikini for almost the whole second story.
- Foreshadowing: At the end of "Master and Cadaver," Maggie dons a bowler hat and fake eyelashes for one eye a la Alex DeLarge from A Clockwork Orange. Turns out it became a subject for a future Treehouse of Horror segment called "A Clockwork Yellow", and Maggie as she appeared in that ending makes an appearance.
- Heroic Sacrifice: Homer himself in the "Tweenlight" segment. He sacrifices himself for Lisa, so the two vampires could suck on his cholesterol-filled blood (and not the good kind of cholesterol).
- Hidden Depths: Edmund is embarrassed when Dracula reveals that he is musically gifted.
- Irony: That's how Homer sees the idea of a cross being used to kill somebody.
- My God, What Have I Done?: Marge is horrified that she and Homer caused the deaths of so many people, a shark and a pelican in "Master and Cadaver". She eats the poisoned pie, which in turn leads to Homer's moment as he cradles Marge's dead body.
- Kubrick Stare: By Maggie, of all people, disguised as Alex DeLarge.
- Our Werebeasts Are Different: Milhouse in the "Tweenlight" segment can turn into a were-poodle.
- Reference Overdosed: All the board games they play are a reference to real board games, even Consternation, which is a reference to the Concentration home game.
- Romantic Vampire Boy: Edmund is an intentional parody of this.
- Swordfish Sabre: Homer uses a mounted swordfish to spear a random pelican.
- Take That!: "Tweenlight" makes fun of almost every thing The Twilight Saga has been building on.
- Tempting Fate: Marge tells Bart and Millhouse to play board games since she thinks video games are too violent. The board game that Bart and Millhouse plays is much more fatal.
- Too Dumb to Live: Millhouse thinking that the number "3" was actually a letter — while playing a literal version of Hangman where if the players guess wrong, they get hanged.
- Vampire Episode: The "Tweenlight" segment.
- Whole-Plot Reference: All of the segments subtly lampoon modern movies: Jumanji for "War and Pieces", Dead Calm for "Master and Cadaver" and (of course) The Twilight Saga for "Tweenlight."
- Would Hurt a Child: The executioner has no qualms about hanging two ten year old boys when they lose a game of hangman.
- Yank the Dog's Chain: Bart manages to beat the board game "Satan's Path" and bring Milhouse back to life. Then he suggests they just play hangman, a game that has no board game pieces. The board game brings it to life, and Bart and Milhouse are hanged when they lose.
