Opening Krusty, as the
Headless Horseman from
The Legend of Sleepy Hollow, holds his laughing head and hurls it at the camera, causing the title, "The Simpsons Halloween Special VI", to appear on-screen in blood.
"Attack of the 50-Foot Eyesores" Homer goes to Lard Lad Donuts to get a "colossal doughnut". Upon realizing that the colossal doughnut is the name of the doughnut that Lard Lad holds and actual doughnuts that size do not exist, he denounces the store and vows to get a colossal doughnut. He returns that night and steals the giant doughnut from the Lard Lad statue in front of the store. In the midst of a freak storm, Lard Lad and the other giant advertising statues come to life to terrorize
Springfield. At
Marge's insistence, Homer eventually returns the doughnut to Lard Lad, but that does not stop Lard Lad and his friends from causing destruction.
Lisa goes to the ad agency that created those advertising characters, and an executive suggests the citizens stop paying attention to the monsters as they are advertising gimmicks, and attention is what keeps them motivated. He suggests a jingle will help distract people from watching the monsters. Lisa and
Paul Anka later perform a catchy song and the citizens of Springfield stop looking at the monsters, who lose their powers and become lifeless (although Homer has to be dragged away from the Lard Lad statue, holding a sign reading "Now With Sprinkles"). Homer is distracted and Lard Lad drops the doughnut, which rolls past
Kang and Kodos, who are trying to hitchhike to
Earth's capital.
Kent Brockman signs off by advising viewers to stay away from destructive advertising, then Homer says "We'll be right back."
"Nightmare on Evergreen Terrace" Bart has a nightmare that
Groundskeeper Willie is out to kill him. He is slashed with a rake, and the scratches are still on his body after he wakes up. Many other students at
Springfield Elementary School also say they were terrorized by Willie in their nightmares. When the students take a test,
Martin—having finished his test first—falls asleep and is strangled to death by Willie in his dream, before waking up and dying in the real world. After Bart and Lisa tell Marge about the incident, she explains Willie burned to death after the thermostat was turned too high, his suffering drawn out by the spendthrift disrepair of the school and the parents of the students looking on and doing nothing; Willie swore that he would take his revenge out on their children in their dreams where their parents could not protect them. Bart, Lisa, and Maggie try not to fall asleep for several days, but eventually, Bart decides that he is going to have to go to sleep and fight Willie in his dream. Bart falls asleep and attempts to find Willie, who appears as a lawn mower. Bart manages to trick Willie into mowing a sandbox containing quicksand, and Willie sinks. Willie recovers and turns into a giant bagpipe spider and is about to kill Bart as well as Lisa, who has entered the dream after also falling asleep. Suddenly,
Maggie appears and uses her pacifier to seal the vent on Willie's spider body, resulting in Willie exploding. The Simpsons children awaken and despite being pleased to be alive, Lisa fears that Willie might still be around "out there, and could back, any time, in any form." As it turns out, a very much alive and well, but apparently far less powerful, Willie exits a bus and tries to scare the children, but loses a shoe as he chases the bus to retrieve a gun he left aboard.
"Homer3" ("Homer Cubed") Patty and Selma visit the Simpsons, driving Bart, Lisa, and even the pets to evade them and consequently leave almost no place for Homer to hide. Desperate to avoid his wife's sisters, he looks behind a bookcase and enters a mysterious new world in which everything is in
3D. Homer explores the peculiar area, and finds that he is trapped within (the rest of the family can only hear his voice). He seeks help from them, but their attempts to rescue him are fruitless. After a cone hits Homer, he throws it point first into the floor and accidentally pierces the fabric of the space-time continuum, creating a
black hole that threatens to pull Homer and the rest of the dimension into it. Bart takes command and enters the third dimension to save Homer after tying a safety rope around his waist. Bart is unable to help, however, and the universe implodes on itself as Homer is sucked into the black hole. Bart is nearly sucked in as well, but is pulled back into the house thanks to his safety rope. Marge is sad that her husband is gone;
Reverend Lovejoy attempts to console her by saying he has gone to "a better place". Homer is sent into the real world, landing in a
dumpster in a
live-action Sherman Oaks, Los Angeles. He walks around, frightened as people stare at him, but then is pleased to find an erotic cake store. ==Production==