1 The Shinning - Treehouse of Horror V
In this parody of Stephen King's "The Shining," the Simpsons become the winter caretakers of Mr. Burns' mountain lodge, where isolation and lack of TV and beer drive Homer into murderous insanity, ultimately thwarted by Marge and the family's escape. Easily number one. Instead of having jokes about love being the solution, it is T.V., and it is one of the best, if not the best spoof of all time, and it is of one of the greatest movies ever.
Easily my favorite, simply because of how many hilarious and quotable moments there are.
I thought this was better than Nightmare on Evergreen Terrace, to be honest. Nightmare on Evergreen is good and all, but this one has Homer going crazy, then tries to kill his family.
Without a doubt, the best Treehouse of Horror segment that ever aired.
2 Nightmare on Evergreen Terrace - Treehouse of Horror VI
Groundskeeper Willie, burnt to death due to a negligence at a PTA meeting, transforms into a Freddy Krueger-like figure, haunting the children of Springfield through their dreams, until Bart and Lisa confront and defeat him in the dream realm. In a parody of The Nightmare On Elm Street movies, Groundskeeper Willie stalks the children of Springfield Elementary in their dreams until Bart and Lisa try to put a stop to this.
Willie's cruel one-liners are even better than Freddy's: "Pleasure to rake your acquaintance!"
Look, it's me, Willie. ROAR, BOO.
Oh no, wait, come back. I left me gun on the bus.
3 The Devil and Homer Simpson - Treehouse of Horror IV
Homer, in desperate need of a donut, sells his soul to the Devil (Ned Flanders) but a trial, led by some of history's most infamous characters, is held to determine the true ownership of his soul, ending in a compromise. I like the part when Homer's head got turned into a donut, and he starts to eat himself. It's so funny!
Homer: I would sell my soul for a donut.
The Devil (Ned): That can be arranged...
Homer: Mmmm, forbidden donut.
Flanders as the devil is awesome. This should really be number one.
Homer sells his soul to the Devil (Ned Flanders) for a forbidden donut.
4 Citizen Kang - Treehouse of Horror VII
Aliens Kang and Kodos abduct and impersonate presidential candidates Bill Clinton and Bob Dole in a bid to take over the world, leading to the public's unwitting election of an alien as President. Kang and Kodos decide to gain power by running for president on Earth.
5 Homer³ - Treehouse of Horror VI
Homer, trying to hide from Patty and Selma, stumbles into a mysterious third dimension, represented by CGI, where he must navigate a strange and dangerous environment before eventually falling into the real world. Awesome TOH, probably the best segment (though Nightmare on Evergreen Terrace could have been a little better if they toned down the over-the-top nightmare fuel).
Homer is transported into another dimension while hiding from Patty and Selma.
Classic! It's funny how insanely expensive that episode was at the time. 3D technology was REALLY young.
6 Terror at 5½ Feet - Treehouse of Horror IV
In this parody of "Twilight Zone's" 'Nightmare at 20,000 Feet,' Bart witnesses a gremlin destroying the school bus but struggles to convince others of the impending danger, ultimately dispatching the creature himself. While catching the school bus, Bart sees a Gremlin on the side who is taking apart the bus. However, no one believes him...
This had me scared out of my wits for some reason.
It's the scariest segment.
7 Time and Punishment - Treehouse of Horror V
Homer accidentally creates a time-traveling toaster and repeatedly alters the past, causing disastrous and comical alterations to the present, eventually settling for a close-enough reality. Using an old toaster, Homer goes back to the time of the dinosaurs and accidentally changes the present day with hilarious outcomes.
The world's physicists are saying, "I told you so." That's what makes this funny. Really, really, really funny. Simply hilarious.
Oh, look. It's raining again.
The creepy forced smile...
8 Bart Simpson's Dracula - Treehouse of Horror IV
Mr. Burns is a vampire who turns Bart into one of the undead, leading the Simpsons to confront the vampires in their lair and Lisa inadvertently causing a vampire pandemic. So, Mr. Burns is not the head, but it's Marge. Marge is the head vampire. Shocking!
9 The Raven - Treehouse of Horror I
This segment narrates Edgar Allan Poe's "The Raven," with Homer as the tormented protagonist, Bart as the raven, and Lisa and Maggie as seraphim, delivering a spooky and humorous rendition of the poem. A timeless original and classic masterpiece. Best segment ever!
James Earl Jones voiced the narrator of the story.
Best Treehouse of Horror segment.
10 The Thing and I - Treehouse of Horror VII
Bart discovers he has an evil conjoined twin, Hugo, locked in the attic, but a twist reveals that Bart is actually the evil twin, leading to a switch in their living arrangements. It absolutely terrified me. My brother and I think it started out scary but worked its way down to not so scary. The scariest was when Marge, Doctor Hibbert, Lisa, and Homer went to search for Hugo, and Bart was left in the house all alone. Then Bart went all quiet, and so did the house. Then suddenly, Bart knew that Hugo was in the house. After Bart said, "I know you're here," Hugo said, "Yes, Bart, I am here." If you don't know who Hugo is, he is Bart's evil twin.
The real evil twin is actually Bart. Hugo is actually the good twin. But due to an error, it's been rendered the opposite. Bart is the good twin, and Hugo is the evil twin.
Bart discovers that he has an evil twin named Hugo who is hiding in the attic.
The Contenders
11 The Fat in the Hat - Treehouse of Horror XXIV
In this Dr. Seuss parody, a murderous cat named "The Fat in the Hat" brings chaos and destruction to Springfield until the town's children decide to fight back. Weird and wacky.
12 Fly vs. Fly - Treehouse of Horror IX
Bart and a fly undergo a science-experiment-gone-wrong, leading to their heads swapping bodies, resulting in the family's quest to return them to their respective bodies. This was even made a year before Catdog, and Bart makes Santa's Little Helper and Snowball II into a half cat and half dog.
The best segment of this episode.
Deserves to be higher.
My second favorite.
13 Lisa's Nightmare - Treehouse of Horror II
In a monkey's paw tale, Lisa wishes for world peace, leading to alien invasion as humanity has disposed of all weapons, causing the world to resort to slingshots and rudimentary devices to fend off the aliens. I love this one, so why is it not in the top ten?!
14 I Know What You Diddily-Iddily-Did - Treehouse of Horror X
The family believes they have killed Ned Flanders in a car accident, leading to feelings of guilt and paranoia, only to discover that he was already a werewolf when they hit him. What? This was so good. It should be in the top tens, I tell ya! Ha, can't imagine something like this happening in real life. It would be sooo scary. Oof.
Ned Flanders was The Devil, and now he's a werewolf?
15 Hungry are the Damned - Treehouse of Horror I
The Simpsons are abducted by aliens Kang and Kodos, who seemingly intend to treat them as honored guests but are suspected of having more sinister culinary intentions, leading to a mutual misunderstanding. The Simpsons are captured by a spacecraft, and Lisa discovers that Kang and Kodos, the aliens onboard, are planning to eat them.
16 Dial Z for Zombies - Treehouse of Horror III
In an attempt to resurrect her cat, Lisa inadvertently raises the dead, resulting in Springfield being overrun by zombies and the Simpson family fighting for survival. Bart and Lisa accidentally raise the dead, and a plague of zombies runs wild in Springfield.
17 Nightmare Cafeteria - Treehouse of Horror V
Due to overcrowding in detention and a meat shortage in the cafeteria, Principal Skinner and the lunch lady start cooking misbehaving students, leading the remaining kids to try to avoid this gruesome fate. The children of Springfield Elementary are one by one being hunted down by Skinner and Lunchlady Doris to be cooked and served as lunch.
That's definitely the scariest, but it's funny.
This is one of the best!
Truly the scariest...
18 School is Hell - Treehouse of Horror XXV
Bart and Lisa are transported to a demonic school in Hell where Bart excels, leading to a dilemma between demonic success and returning to the normal life of underachievement. I like the one where Lisa and Bart are in Hell Primary School!
19 Send in the Clones - Treehouse of Horror XIII
Homer’s ability to duplicate himself with a magical hammock results in an army of reckless Homers, forcing Springfield's citizens to combat the chaos induced by the clones. One of the final "good" segments, alongside "The Places You'll D'oh" and "A Clockwork Yellow", and the only good one from Zombie Simpsons (Seasons 12-19).
A rather great segment. I agree that TOH was one of the last good Simpsons traditions before it itself went downhill around 2005.
Peter Griffin was among the clones.
20 Bart's Nightmare - Treehouse of Horror II
In a dream, Bart has omnipotent powers and turns everyone and everything into a whim-fulfilling entity, leaving the town walking on eggshells to avoid his displeasure until they revolt.
21 In the Na'vi - Treehouse of Horror XXII
Bart and Milhouse are avatars in a parody of James Cameron's "Avatar," tasked with retrieving a precious mineral but facing moral decisions when Milhouse falls in love with a native. In a parody of Avatar, Bart and Milhouse are sent to Rigel 7 to retrieve a valuable mineral called Hilarium.
22 Wiz Kids - Treehouse of Horror XII
In a Harry Potter-like universe, Bart and Lisa are wizards-in-training who must prevent the evil Lord Montymort from regaining physical form by stopping him from capturing Lisa's magical essence.
23 The Ned Zone - Treehouse of Horror XV
After suffering a head injury, Ned Flanders gains the ability to foresee people's deaths, which includes a vision of him killing Homer, eventually leading to a catastrophic event when he sees the town's destruction.
24 Clown Without Pity - Treehouse of Horror III
Homer buys Bart a cursed Krusty doll, which attempts to kill Homer repeatedly, until the “evil switch” on the doll's back is discovered and corrected by a repairman.
25 Hell Toupee - Treehouse of Horror IX
Snake's hair, implanted onto Homer after Snake's execution, possesses him to seek revenge on the witnesses who testified against Snake, leading to a horrifying showdown.