The Simpsons has been running for 38 years (God, I'm old) and in that time, it's aired 37 annual "Treehouse of Horror" episodes. Featuring a trio (or more) of tales of an ostensibly (but sometimes loosely...) Halloween flavor, these Halloween specials have often been a highlight of their respective seasons (especially during some of the middling "middle years seasons"), thanks in part to their ability to break conventional boundaries of both Simpsons' storytelling and animation.
All told, there's over 100 different Treehouse of Horror segments. I briefly toyed with the idea of ranking them all, then came to my senses and settled on 31 (because October).
I'll just have to save the "every Treehouse segment ranked" piece for when the show ends. If it ever does.
#31 - Master and Cadaver
(Treehouse of Horror XXI, 2010)
A segment which succeeds more on tone than jokes or scares, this has an almost Hitchcockian air of suspense and weirdness about it, as characters and events alike are revealed to be not what they seem.
#30 - Coralisa
(Treehouse of Horror XXVIII, 2017)
I honestly couldn't quote a line of dialogue or reference a specific gag in this segment, but it makes the cut thanks to its use of stop-motion animation (and in expertly aping the surrealist, "scary but not in the way you think" tone of Coraline).
#29 - Dial ‘M’ for Murder or Press ‘#’ to Return to Main Menu
(Treehouse of Horror XX, 2009)
"Crisscross!"
This is the full-fledged Hitchcock parody segment, with Bart and Lisa starring in a lose adaptation of Strangers on a Train in order to eliminate their respective teachers. It's the little things that sell this one, from the gray tone to the score right down to some of the shot construction, all of which channel the essence of Hitch.
#28 - The Greatest Story Ever Holed
(Treehouse of Horror XXIII, 2012)
One of the rare original "Treehouse" stories, in that it's not adapting, parodying or homaging an existing story or style, in which Professor Frink creates a miniature black hole that Springfield, not surprisingly, can't resist feeding their junk. The shots of things gradually being sucked into the hole are fun, but the twist at the end helps put it over the top.
#27 - Heck House
(Treehouse of Horror XVIII, 2007)
Another mostly original tale, this one of what I call a "pure Halloween" "Treehouse" segment, one which draws on the mythology, traditions, and iconography surrounding the holiday for inspiration (there are surprisingly few of them, and this isn't the only one on this list). Ned Flanders gaining demonic powers in order to scare the children of Springfield into being good isn't the most unique of ideas, but the "torture sequences" (and the pre-demonic attempts to scare the kids) make the most of the premise.
#26 - Desperately Xeeking Xena
(Treehouse of Horror X, 1999)
Very much a story of its time — there's a starring role for Xena, excuse me, Lucy Lawless and Phantom Menace references — this is nevertheless a fun story that sees a superpowered Bart and Lisa (Stretch Dude and Clobber Girl) fight Comic Book Guy/The Collector. It's filled with fun homages to Batman '66-esque tropes, and ends on a killer punch line.
Plus, this is the story which gave the world, "A wizard did it" as the default answer to any inconsistencies' in a property's lore or storytelling.
#25 - Death Tome
(Treehouse of Horror XXXIII, 2022)
If you ever wondered what The Simpsons would look like if it was an anime, this is the answer. Like "Coralisa," this stands out for the change in animation style, and the level of detail put into the creation of this alt-Springfield is legitimately stunning. But the story is solid too, perfectly casting Lisa as the character struggling with the question of whether bad things can be used in the purpose of good.
#24 - The Day the Earth Looked Stupid
(Treehouse of Horror XVII, 2006)
The real meat of this episode is its not-so-subtle political satire, which views the sepia-toned arrival of aliens Kang and Kodos (who come to Earth in the wake of the War of the Worlds radio hoax perpetrated by a Orson Welles) through the lens of the Iraq War (which you'd think would date it but, sadly, does not).
But what gets it on this list in the first place is how much I laugh my ass off at this exchange every time.
Orson Welles: The devastation is incredible! They're grinding up the bodies of human beings!
Sound technician: (uses a wisp to grind up cornflakes)
Orson Welles: Now they're riding horses in the rain!
Sound technician: (clacks coconut halves against a wooden board while pouring water into a tray)
Orson Welles: Now they're playing the xylophone while bowling near an airport.
Sound technician: (holds up sign reading "Screw you" and leaves)
#23 - Nightmare on Evergreen Terrace
(Treehouse of Horror XXIV, 2013)
One of the series' better straight horror movie adaptations (with A Nightmare On Elm Street being particularly well-suited to animation), with a perfectly cast Groundskeeper Willie as Freddie Krueger. This also climbs the ranks a few spots for historical reasons, as this is the story which gifted the world "lousy Smarch weather." (spoken shortly before Homer turns up the furnace and burns Willie alive, setting in motion his murderous revenge spree).
#22 - Freaks No Geeks
(Treehouse of Horror XXIV, 2013)
Tod Browning's Freaks is a legitimately unsettling film, and while this loose adaptation of it doesn't really even try to create that sensation, it does do an effective job of parodying circus/carnival tropes and story beats while playing up some of their more eerie elements. It's also fun to see Homer playing, not just a super jerk, but a legitimately bad guy done in by his greed.
#21 - Ei8ht
(Treehouse of Horror XXXIV, 2023)
"Plot" has never been a huge concern of "Treehouse" stories, with even some of the best more or less just...stopping, rather than coming to any kind of elegant conclusion. But "Ei8ght" manages to deploy a well-crafted (if obvious) mystery in its ten odd minutes of runtime, while also doing more with the premise of "what if Sideshow Bob killed Bart?" than the much more ballyhooed story with the same premise did in 2015's "Treehouse of Horror XXVI."
#20 - I’ve Grown a Costume on Your Face
(Treehouse of Horror XVI, 2005)
Another "pure Halloween" original story, based on the simple yet elegant premise of "what if a witch turned everyone into whatever their Halloween costume is?" Simply a fun segment.
#19 - The Monkey's Paw
(Treehouse of Horror II, 1991)
Is there anything worse than a sandwich where the turkey is a little dry?
The standout segment of the second "Treehouse of Horror" episode, the one which established the concept wasn't a done-in-one, in addition to the "be careful what you wish for" message of the original story, "Monkey's Paw" is one of the series' earliest attempts to grapple, via the series itself, at the massive sudden popularity of the series, coming during the first great wave of Simpsons-mania, in which Bart Simpson t-shirts were being banned in schools and which would inspire pithy and mockable comments from President Bush the Elder.
#18 - School Is Hell
(Treehouse of Horror XXV, 2014)
In addition to being another visually fun segment, with tons of great visual gags and details packed into the Hell-set scenes, what really sets this one apart is a surprisingly-sweet Bart/Homer story at its center. It turns out, apparently, that all the pair needed to bond was a trip to Hell.
#17 - Scary Tales Can Come True
((Treehouse of Horror XI, 2000)
Suzanne the Witch: Stop your chattering and sweep! This house is filthy!
Bart: What'd you care? It's not like you have any friends.
Suzanne: I have a boyfriend!
Lisa & Bart: Pssht, yea, sure.
Suzanne the Witch: What? I do!
Lisa: Oh, yeah? What's his name?
Suzanne the Witch: George.. [looks at the cauldron] Cauldron.
Lisa: "George Cauldron"? Maybe he can fix me up with Ed Ladle!
Followed by the punchline of George Cauldron showing up to take Suzanne on their date?
Perfection.
#16 - The Raven
(Treehouse of Horror, 1990)
Neither the funniest nor scariest of segments (as noted by Bart and Lisa in the episode's between-segments runner), "The Raven" is nevertheless a classic for the way it serves as punctuation mark on the end of the statement made by the entirety of the first "Treehouse of Horror," that this would be a show unafraid to take big swings.
Also, there's simply nothing wrong with just getting to hear James Earl Jones read "The Raven."
#15 - It's the Grand Pumpkin Milhouse
(Treehouse of Horror XIX, 2008)
It's surprising it took the series as long as it did to use its animated Halloween special to send up arguably the most famous animated Halloween special, but the wait was worth it, as the end result does a fantastic job of honoring the spirit of the original (aside from obvious stuff like the Marge trombone gag, the attention to detail in recreating It's The Great Pumpkin, Charlie Brown's watercolor animation style is stunning) while still giving their take on it that patented Treehouse/Simpsons take that is darker and more jaded.
#14 - The Genesis Tub
(Treehouse of Horror VII, 1996)
"I've created Lutherans!"
This makes the list less for its humor (though it has its moments) or because its particularly scary (aside from existential fears), but because it's fun little treatise on the nature of religion and the vagaries of existence, with Lisa viewed as a god-like creator and Bart her rival devil figure by the society Lisa accidentally creates in her science fair entry, which is born and evolves to the level of being able to create a debiggulator to bring their god down to their level in the span of 24 hours.
#13 - Hungry are the Damned
(Treehouse of Horror, 1990)
The standout segment of the first Treehouse, and the introduction of Treehouse mainstays Kang and Kodos, Hungry and the Damned succeeds on the strength of one really excellent joke ("How To Cook For Forty Humans") and the way it sets a template for much of the segments to come.
It's also the first instance of a "Lisa ruins it for everyone" plot, which becomes an oft returned to device.
#12 - Attack of the 50 Foot Eyesores
(Treehouse of Horror VI, 1995)
Just looking at that screenshot, I can see the Billboard Monsters punching to the beat of Paul Anka's catchy tune. "Just don't look! Just don't look!"
#11 - Time and Punishment
(Treehouse of Horror V, 1994)
Time-travel hijinks is another well the series will return to again, but this original foray into that realm remains the best, both for the way the salt-of-Earth Homer grapples with the bizarre situation he's found himself in, and for all the wild alternate realities the segment gets to depict
#10 - Citizen Kang
(Treehouse of Horror VII, 1996)
As a piece of political satire, this segment is one of the best things The Simpsons has ever created. But this isn't a list of the best political satire segments, it's about Halloween stories. And aside from Halloween's temporal closeness to Election Day and the presence of Kang and Kodos, there's not much Halloween-y about this one.
Also, some of its "both sides are essentially the same" humor, while consistent with the series' view on politics, especially at the time, hasn't aged as well over the last 10 years, as it's become more and more clear there are (and have always been) fundamental differences between the two sides that extend beyond disagreements over tax policy or deficit spending into the realm of "thinks a certain type of person should or shouldn't be allowed to exist" and "is openly fascistic and emulating the policies of the Nazis."
#9 - Terror at 5 1/2 Feet
(Treehouse of Horror IV, 1993)
Early Treehouse dipped into Twilight Zone adaptations fairly frequently; this is one of the best. Casting Bart in the "William Shatner sees a gremlin on the plane wing" role adds an element of "Boy Who Cried Wolf" energy to the story, but it succeeds thanks to the way it makes the tight, limited confines of a school bus feel as expansive and packed with oddball characters as the show itself.
#8 - Easy Bake Coven
(Treehouse of Horror VIII, 1997)
The best of the Pure Halloween segments, this has fun with the conventions of the Salem Witch trials (rightly calling them out as chiefly a tool to oppress woman), rolling them into a wider "origin of Halloween" story that includes (humorously incorrect) explanations for costumes and for trick-or-treating.
#7 - Night of the Dolphins
(Treehouse of Horror XI, 2000)
I love this one so much. It's doing several adaptations and homages (Night of the Living Dead, Jaws, The Birds) at once, while underscoring everything with the batshit absurdity of talking killer dolphins come to reclaim the land for themselves. It's funny and clever and scary - everything you want a good Treehouse segment to be.
It's also another "Lisa ruins everything" story AND a "it ends with the destruction of the world/society" story, another frequent trope of the series.
#6 - Dial Z for Zombies
(Treehouse of Horror III, 1992)
Bart: Dad, you killed the zombie Flanders!
Homer: He was a zombie?
Treehouse's first and still best dalliance with zombies, every moment of this is packed with something great, from Bart's spells (consisting of everything from the names of discount retailers to game show hosts), to Homer's concern over the car ("But the car's okay?") to the litany of zombified denizens of Springfield (and Shakespeare) Homer cuts down.
#5 - Bart Simpson's Dracula
(Treehouse of Horror IV, 1993)
While ostensibly a parody of Bram Stoker's Dracula, this mostly just lifts some of the iconography of the film (like the weird hair). Ultimately, it's rather a much broader sendup of vampire tropes, referencing everything from Dracula to The Lost Boys to Salem's Lot. It's such a comprehensive and well-executed parody that it would take the introduction of an entirely new suite of elements to the vampire mythos (in the form of Twilight) before the series would return to the subject.
#4 - Clown Without Pity
(Treehouse of Horror III, 1992)
The whole Frogurt good/bad sequence got really played out there for awhile, but even then, it was a standout segment. Like the rest of the stories from the series' best Treehouse of Halloween III, it's gag-per-minute ratio is off the charts.
#3 - King Homer
(Treehouse of Horror III, 1992)
Carl: Hey, I heard we're goin' to Ape Island.
Lenny: Yeah, to capture a giant ape. I wish we were going to Candy Apple Island.
Charlie: Candy Apple Island? What do they got there?
Carl: Apes, but they're not so big.
#2 - The Devil and Homer Simpson
(Treehouse of Horror IV, 1993)
From the clever reveal of Flanders as the Devil ("It's always who you least expect") through the Jury of the Damned, all the way to Marge's quick thinking to save Homer's soul (if not his human head), this is a segment that just builds and builds and builds, piling one great bit onto another. As a bonus, it's also a fantastic Lionel Hutz episode ("I watched Matlock in a bar the other night. The sound wasn't on, but I think I got the gist of it.")
#1 - The Shinning
(Treehouse of Horror V, 1994)
Sometimes, when you do these lists, you want to zag, to place at the #1 spot something unexpected, something hot take-y, something that will get people talking.
And sometimes, you just have to admit you can't beat the power of "No TV and no beer make Homer...something something."
Is this adaptation of Stanley Kubrick's The Shining better than Stanley Kubrick's The Shining itself? I might be inclined to argue that it is. But even if it's not, it's hard to argue that this isn't the best "Treehouse of Horror" segment, a perfect execution of adaptation, horror, and humor, a Platonic ideal to which all Treehouse segments should strive to reach.
