Bart and Milhouse get trapped in a cursed board game in "War and Pieces," Homer and Marge's honeymoon trip on a boat gets interrupted by a castaway who may be a murderer in "Master and Cadaver" and Lisa falls for a preteen vampire called Edmund in "Tweenlight."
- All Just a Bath Time Daydream: "Master and Cadaver" is revealed to be a daydream in Maggie's imagination.
- Crazy Jealous Guy: Homer in "Master and Cadaver."
- Dracula: He is Edmund's father.
- 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.
- Unable to live with her guilt for the deaths of the innocent people in "Master and Cadaver", Marge eats a poisoned pie.
- 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).
- Irony: That's how Homer sees the idea of a cross being used to kill somebody.
- Kubrick Stare: By Maggie, of all people, disguised as Alex DeLarge.
- 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.
- Take That!: "Tweenlight" makes fun of almost every thing Twilight has been building on.
- Too Dumb to Live: Milhouse 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.
- 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) Twilight for "Tweenlight."