The Spookiest Simpsons “Treehouse of Horror” Stories of All Time

9. The Raven (Treehouse of Horror)

An adaptation of Edgar Allen Poe’s poem of the same name, “The Raven’s” significance doesn’t lie in its humor but more in what it meant for the show at the time and ever since. Many seem to forget that The Simpsons wasn’t regarded as an “important” show right off the bat; it had to earn its reputation as a smart, satirical sitcom and “The Raven” is regularly cited as the moment when The Simpsons went from merely being a funny show to being an intelligent one as well. Now, it’s hard to think of Poe’s classic poem without seeing Bart the Raven tormenting Homer in his study. It also helps that the whole thing was narrated by James Earl Jones, whose distinctive voice lends the proceedings a unique tone that walks a near-perfect line between being humorous and creepy. The Simpsons would go on to have many better Halloween episodes over the years, but “The Raven” was so important to the show as a whole that it deserves recognition all the same.

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8. The Monkey’s Paw (Treehouse of Horror II)

The Simpsons upped its game with the second Treehouse of Horror special, framing each of the episode’s short stories as nightmares that Lisa, Bart, and Homer experience after eating too much Halloween candy. While each one of these segments is a classic, Lisa’s dream is the frontrunner. Inspired by the short story of the same name by W.W. Jacobs, “The Monkey’s Paw” is a hilarious spin on the “careful what you wish for” idiom, as the Simpson family comes into possession of a cursed monkey’s paw that grants them wishes with unintended negative consequences. While it’s entertaining enough seeing how each wish backfires on the family, the episode hinges on a clever shift that shows how everything works out perfectly for Ned Flanders when he uses the paw, including the delightful visual gag of showing his newly acquired castle next to The Simpson homestead. And who can forget the memorable Cold War-tinged exchange between Kang and Kodos, as the aliens predict that humanity will lock itself in a deadly arms race of ever more terrible boards with nails in them?

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7. Nightmare on Evergreen Terrace (Treehouse of Horror VI)

As the title suggests, “Nightmare on Evergreen Terrace” is a direct spoof of Wes Craven’s classic horror film A Nightmare on Elm Street, with everyone’s favorite Scotsman Groundskeeper Willie standing in for the Freddie Krueger role. While most of The Simpsons Halloween segments are more hilarious than they are scary, “Nightmare on Evergreen Terrace” is legitimately chilling in parts, as Willie’s dreamscape assaults on the children of Springfield strike a nice balance between being humorous and unsettling. All in all, it’s an entertaining spoof of a horror classic, made all the better by some inspired character design work — the Willie spider bagpipe creature is truly the stuff of nightmares — and in typical Simpsons fashion, truly memorable quotes (“lousy Smarch weather”).

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6. Terror at 5 and 1/2 Feet (Treehouse of Horror IV)

A parody of the classic Twilight Zone episode Nightmare at 20,000 Feet, “Terror at 5 and 1/2 Feet” finds Bart witnessing a gremlin slowly destroy the Springfield Elementary school bus while trying to no avail to convince the other passengers of the creature’s existence. The segment gets a lot of mileage out of introducing creative new ways for the gremlin to further compromise the bus’s integrity and strikes that perfect Treehouse of Horror balance between being frightening and hilarious, perhaps best represented by Ned Flanders’s doting love for the gremlin quickly turning to terror, as the segment caps off with the creature brandishing Ned’s severed head.

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5. Clown Without Pity (Treehouse of Horror III)

Perhaps best remembered for giving us the classic “Frogurt” exchange, “Clown Without Pity” is simply a great send-up of the Chucky films, with the murderous doll being played by none other than Krusty the Clown. The meat of the segment deals with the Krusty doll’s desire to kill Homer, which by itself would make for a perfectly fine entry in the Treehouse of Horror canon. Instead, the writers cleverly introduce the twist of the doll having been set to “evil” the whole time, which not only represents a bit of sly commentary on the dangers of some children’s toys but turns the “doll trying to kill Homer story” on its head by having the newly-lovable Krusty essentially become Homer’s slave by the end. Now that’s a truly horrifying outcome!

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 4. The Devil and Homer Simpson (Treehouse of Horror IV)

Even if “The Devil and Homer Simpson” wasn’t a Halloween-themed masterpiece, it would be fondly remembered for the unforgettable image of Homer’s doughnut head alone. Luckily, this short from season five is most definitely an undisputed classic, showcasing how far Homer would be willing to for a doughnut. This short is jam-packed with classic moments, from the inability of Hell’s minions to successfully torture Homer with “all the donuts in the world” to the courtroom drama that pits Ned Flanders the Devil and his “Jury of the Damned” against the ever-incapable Lionel Hutz. This one’s a true gem.

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3. Time and Punishment (Treehouse of Horror V)

Arguably one of the greatest (and funniest) takes on the butterfly effect time travel theory, this segment comes from what is arguably the best Simpsons Halloween episode of all time, season six’s Treehouse of Horror V. While attempting to fix the family’s toaster, Homer inadvertently creates a time machine and accidentally alters the future through a number of mishaps. The very concept of giving Homer time travel abilities is terrifying in itself, but the real joy of this short comes from seeing the many alternate futures the writers come up with. Everything from a world that rains donuts to a fascist state run by Ned Flanders comprise Homer’s journey through time and overall, nothing about “Time and Punishment” disappoints…other than that there isn’t more of it.

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2. Citizen Kang (Treehouse of Horror VII)

“Citizen Kang” is such a tour de force of political satire, it makes you wish that it could have taken up an entire episode if only to hear more of Kang and Kodos’s hilarious campaign promises as they run for the presidency of the United States. Giving us such memorable quotes as “abortion for some…miniature American flags for others!” and “Go ahead: throw your vote away!”, “Citizen Kang” represents The Simpsons at its most biting and culturally-aware. There may not be much in it that could be considered Halloween-themed, but by the time the show was in its eighth season, the Treehouse of Horror specials had abandoned the idea of simply parodying familiar horror stories. Instead, the specials had become a vehicle for the writers to truly let loose and break the rules; we’d say having Homer accidentally kill the President of the United States and his running mate while a pair of alien twins run for office is a pretty good illustration of that.

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1. The Shinning (Treehouse of Horror V)

It’s honestly difficult to think of a better direct parody segment on The Simpsons than Treehouse of Horror V‘s spoof of The Shining, cleverly titled “The Shinning” (careful, do you want to get sued?). The Simpson family travels to a remote hotel owned by Mr. Burns to be its winter caretakers, but after Burns deliberately strips the place of beer and cable, Homer quickly starts losing his mind. The fact that “The Shinning” is able to cram a pretty faithful recreation of Stanley Kubrick’s two and a half-hour film is impressive in itself, but the reason this short stands above all the rest lies with its absolutely stellar jokes and loving reverence for the source material, right down to the music and the requisite shot of the bloody elevator (“That’s odd. Usually the blood gets off at the second floor”). All-in-all, “The Shinning” is the definitive Treehouse of Horror experience and arguably one of the greatest moments in Simpsons history, period.

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Nick Steinberg (@Nick_Steinberg)