The Simpsons Treehouse of Horror Best Segments, Ranked

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When one thinks of Fox’s immortal animated sitcom The Simpsons, what typically comes to mind is the biting satire of American life, the hundreds of iconic characters and the sheer meteoric number of episodes across its over 30-year run. For 32 seasons and counting, the legacy of Matt Groening’s primetime creation has become synonymous with the rise of modern adult-oriented cartoons and the history of TV animation in general. However, for most fans, The Simpsons has also revolutionized the art of a time-tested tradition that is as old as storytelling itself: the scary story.

Every year, the howling autumn winds see the return of costume parties, pumpkin spice confectionaries and of course, The Simpsons’ annual “Treehouse of Horror” special. In a yearly tradition that started in the series’ second season, fans have been able to celebrate Halloween as only The Simpsons can, in episodes that many consider to be the best of the entire series. Every “Treehouse of Horror” tells an anthology of three hilariously spooky tales that have become just as much a part of the shows’ identity as the characters themselves. For as iconic as The Simpsons has become for its grounded satire, this yearly Halloween special allows the show to be more fantastical and outlandish in its stories and animation as it spoofs everything from classic literature of the macabre to pulp-horror films, and all that lies between.

For those looking to sample only the best of the bunch instead of binging them all like Halloween candy, here is list of the top 13 best “Treehouse of Horror” segments.

13. “The Island of Dr. Hibbert” (Season 14, Treehouse of Horror XIII)

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Based upon H.G. Wells’ The Island of Dr. Moreau, this segment pits Springfield’s kindly ever-laughing physician as the mad scientist who transforms the human guests of his island into anthropomorphic animal hybrids. What makes this segment so memorable is the fun character designs of favorite Springfieldians in their beast forms. Ned Flanders is turned into a cow centaur (complete with udders), book smart Lisa is now a wise owl and Police Chief Wiggum is now a pig, just to name a few. “The Island of Dr. Hibbert” stands as a solid example of what “Treehouse of Horror” can do: turning scary stories on their ear to minimize the horror and amp up the laughs in cartoony ways.

RELATED: ‘The Simpsons’: The 11 Best Guest Stars Who Didn’t Play Themselves

12. “I’ve Grown a Costume on Your Face” (Season 17, Treehouse of Horror XVI)

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When a real witch is humiliated after losing the town’s costume contest, Springfield’s citizens are cast under a magic spell, transforming them into the costumes they are wearing. In its short runtime, this segment takes full advantage of its premise in showing the pros and cons of being turned into one’s costume through great visual gags and designs. While Marge is turned into a real living skeleton who cannot keep herself together, Sideshow Mel gets to be a real web-slinging Spider-Man. The spell creates a divide between in the town between those who want to change back to normal and those who want to remain in their enchanted masquerade.

11. “Married to the Blob” (Season 18, Treehouse of Horror XVII)

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Over the years, “Treehouse of Horror” specials have loved to put the slovenly food-loving Homer in the role of various monsters and beasts, such as King Kong or Godzilla. Depicting Homer as a ravenous man-eating slime seems like perfect typecasting and a choice fit for a parody of The Blob. After Homer ingests an alien ooze, his appetite for becomes more insatiable than usual as he begins to swallow fat people whole into his gelatinous gullet. Despite arbitrary guest appearances from Dr.Phil and Sir Mix-a-Lot, this segment reaches a deliciously morbid ending and follows in the tradition of attributing classic horror archetypes to favorite series characters.

10. “It’s the Grand Pumpkin, Milhouse” (Season 20, Treehouse of Horror XIX)

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In It’s the Great Pumpkin, Charlie Brown, Linus waited all night in the pumpkin patch to see the fabled Great Pumpkin fly through the air and rain gifts on good children. In this thinly veiled parody, Milhouse instead meets the Grand Pumpkin, who wreaks a terrible vengeance on Springfield over the various atrocities inflicted on his kind every year. The art direction of this segment fully immerses itself in the classic Peanuts style with low framerate walk cycles, blocky designs and painterly backgrounds. Aside from loving spoofs of the original Peanuts special, the bulk of the segment’s comedy comes from the Grand Pumpkin himself as seeks revenge for his fallen fellow produce and wishes for “pumpkin segregation.”

9. “Easy-Bake Coven” (Season 9, Treehouse of Horror VIII)

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In 17th century Springfield, Crucible-style witch hunts weed out and burn the town’s suspected witch population. Wild accusations are thrown out at random and throwing the accused off a cliff is characterized as “due process.” Amid the hysteria, Goodwife Marge is revealed to be a real witch and is joined by her sisters to abduct and eat the local children. The crux of this segment’s comedy is the village’s fear-driven mania for hunting down witches. Historically rooted ignorant witch trials are depicted with a modern callousness and petty rationalizations. Seeing Marge as a cackling wicked witch is also a refreshing change from her typically kind-hearted nature.

8. “Desperately Xeeking Xena” (Season 11, Treehouse of Horror X)

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Not every “Treehouse of Horror” segment is rooted in the terrifying or the macabre. Often, the yearly Halloween special gives the show’s writers and artists a chance to be as weird as they can and indulge in styles of parody they otherwise could not do in earnest on a regular episode. In this segment, Bart and Lisa are granted superpowers as the result of a nuclear accident and must fight Comic Book Guy’s alter ego, The Collector, to save guest star Lucy Lawless (Xena: Warrior Princess) from his fanboy clutches. Complete with a catchy theme song and hackneyed puns, the segment goes full force into light-hearted superhero camp that emulates the likes of the 1960s Batman series and the silver ages of comics.

7. “The Terror of Tiny Toon” (Season 10, Treehouse of Horror IX)

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After a nuclear-power remote control pulls them into the TV, Bart and Lisa come face to face with their favorite cartoon characters, Itchy and Scratchy. The gory antics of The Simpsons’ answer to Tom and Jerry have been a highlight of every episode in which they have appeared. Now, the kids finally share the screen with the cat-and-mouse team and find themselves on the receiving end of their ultra-violent antics. This segment turns into a slasher chase through an animated world of insanity akin to Eddie Valiant’s visit to ToonTown in Who Framed Roger Rabbit. This segment is easily one of the most cartoony moments in the entire show.

6. “Citizen Kang” (Season 8, Treehouse of Horror VII)

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Every few years, there occurs something even scarier in the Fall than Halloween night, and it happens just a couple days after the holiday: election day. This segment aired during the 1996 presidential race between Bob Dole and Bill Clinton and shows both candidates abducted and “bio-duplicated” by fan-favorite aliens, Kang and Kodos. Homer wages a one-man war against the space reptiles to expose their plot and free the prospective heads of state. Of all the “Treehouse of Horror” segments, this one is easily one of the most quoted by fans all year round. The rhetoric the aliens use to persuade voters, in the guise of Dole and Clinton, is hilariously monotoned and forebodingly tyrannical, which the undecided voters of Springfield eat up.

5. “Clown Without Pity” (Season 4, Treehouse of Horror III)

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Child’s Play. Annabelle. Small Soldiers. A living doll wreaking havoc with murderous intent is a popular horror trope that of course finds its way into the Simpson home. As a late-birthday present, Homer gives Bart a mysteriously acquired Krusty the Clown doll. The doll is revealed to be evil and sets his little plastic eyes on stalking and killing Homer by any means necessary. The high tension of a sentient psychopathic doll on the loose is fizzled out almost immediately once his switch is set from EVIL back to GOOD. Like any other toy in need of fixing, all that was needed to stop the Krusty doll was the instructions, but at least it came with a free frozen yogurt!

4. “The Shinning” (Season 6, Treehouse of Horror V)

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Stanley Kubrick’s The Shining, based on the novel by Stephen King, is a masterpiece of cinematic horror with chilling atmosphere, visceral performances and editing techniques that capture the dwindling sanity of its characters. “The Shinning” takes the film’s iconic imagery and tension and condenses it down to seven minutes. While Jack Torrance was driven to madness by the deafening isolation and departed spirits of the Overlook Hotel, the absence of TV and beer is what makes Homer go crazy. This segment is the finest film parody to ever come out of any “Treehouse of Horror” special.

3. “The Devil and Homer Simpson” (Season 5, Treehouse of Horror IV)

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Homer loves donuts so much, he would sell his soul for one. Luckily, the Devil, in the form of Ned Flanders, has one to offer in exchange. When Homer finishes his “soul donut”, he is condemned to an eternity in Hell, unless the family can win back his soul in a legal battle at the mercy of biased court of the damned. Apart from the vibrant colors and striking visuals of Homer’s trip to Hell, the strongest appeal of this segment is seeing jolly bible-thumper Ned Flanders as the Lord of Darkness himself. Despite being the embodiment of evil and the villain of the tale, Flanders still remains his goofy lovable self, even with goat-legs and horns. It is this kind of ironic juxtaposition that can only be done in a Simpsons Halloween story.

2. “Homer3” (Season 7, Treehouse of Horror VI)

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The Twilight Zone has heavily inspired many “Treehouse of Horror” segments in the show’s earliest seasons, including “Terror at 5 ½ Feet”, “The Genesis Tub” and “The Ned Zone”. “Homer3” borrows from the Twilight Zone episode “Little Girl Lost”, wherein a child’s voice can be heard from the ceiling as she is trapped in a mysterious outer dimension. This segment finds Homer stuck in a three-dimensional world behind his bookcase as his friends try to rescue him. The mystique of Twilight Zone’s bone-chilling scenario is now treated like a minor neighborhood inconvenience. The true star of this segment is the dazzling 3D animation. Released less than a month ahead of the original Toy Story, the groundbreaking computer animation by Pacific Data Images (who would later go on to become DreamWorks Animation) made this segment an instant classic and a landmark moment in the show’s history and CGI animation in general.

1. “The Raven” (Season 2, Treehouse of Horror I)

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The inaugural “Simpsons Halloween Special” not only birthed the basis of a yearly tradition that continues on to this day, but it also delivered the very best segment that has yet to be topped over 30 years later. Guest star James Earl Jones eloquently recites an abridged version of Edgar Allen Poe’s “The Raven” as the Simpson family reenacts it with Homer as the mournful lead and Bart as the titular raven. Much like how Looney Tunes artfully utilized classical music, this segment stays true to the reverence of the original text’s vernacular while executing it with a cartoony medium. Dan Castellaneta reads Poe’s words with such conviction while also maintaining the dopey speech patterns of Homer. The segment also veers away from outright parody and conveys the mood and atmosphere of the original poem with a sincerity that celebrates Poe’s work rather than lampoons it. When it comes to “Treehouse of Horror” segments in all the years that followed and all the seasons to come, this segment shall be bested… nevermore.

KEEP READING: 9 Spooktacular Animated Halloween Episodes of the 21st Century

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Austin Allison
(13 Articles Published)

Austin Allison is an Animation Feature Writer for Collider. He is also a freelance artist, avid cartoon watcher, and occasional singer. His karaoke favorites include singing Rainbow Connection as Kermit the Frog and Frank Sinatra’s My Way as Goofy. Check out his Instagram (@a_t_allison) and Twitter (@atallison_) for his latest artwork and to submit commssions.

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