Bart presents this year's Halloween Special. In a Night Gallery parody, he uses paintings to tell the horror stories.
First up is "The Devil And Homer Simpson". Homer is out of donuts at work, so he sells his soul to the Devil, who turns out to be Ned Flanders. Homer saves the last bite of the donut so that Flanders does not get his soul, however, he eats it the next night during a sleepwalk.
Lisa argues that her father has the right to a fair trial - where Marge shows the jury a photo, signed by Homer, promising Marge his soul forever. Flanders loses, but converts Homer's head into a donut.
The next story is "Terror At 5½ Feet". On the way to school, Bart sees a gremlin on the side of the bus, but no one believes him. Bart takes an emergency flare and throws it out the window at the gremlin, knocking it off the bus. When the bus gets to school, it falls apart, and Bart is sent to a mental institution because of his disruptive behaviour.
The final segment is "Bart Simpson's Dracula". The Simpsons visit Mr. Burns' mansion in Pennsylvania, where Lisa suspects something odd. She and Bart stumble across Mr. Burns' secret vampire lair, and Bart is captured by the vampires.
Mr. Burns returns Bart to his parents, who don't believe Lisa that he is a vampire. However, they soon realize and go to kill Mr. Burns. It turns out, though, that Burns is not the head vampire, Marge is. The whole family are about to turn on Lisa, when they cheer "Happy Halloween" and start singing a Christmas song.