A couple of weeks ago, I dived into the sewer containing the worst of what a Simpsons’ Halloween had to offer, but now the spookiest night of the year has arrived, I think it’s time to take a look at the best. These episodes capture the height of the writing team’s creativity and hilarity. Even standing up as some of the best Simpsons episodes out there, Halloween or otherwise.
10 – Treehouse of Horror XIII
Original Airdate: 3rd November 2002
Segments: Send in the Clones; The Fright to Creep and Scare Harms; The Island of Dr Hibbert
Send in the Clones is an absolute classic. I never thought that watching Homer interact with himself could be so fun to watch, but it’s absolutely perfect for this segment. Homer hits the right level of stupid here, still feeling competent enough to make some of the more complex jokes work. The supporting cast does a great job at framing the problem and gives Homer more to bounce off of so his star shines all the brighter.
The Fright to Creep and Scare Harms is the least interesting of the bunch, but it’s not bad by any stretch. It focuses quite heavily on the plot, which means that there aren’t many grand jokes or parodies. Speaking of, as this isn’t a parody of anything, most of the jokes are quite simple, but a handful of them still got a giggle out of me. It’s certainly not making any remarkable satirical statements about gun violence, but I don’t think it needed to either, The Simpsons’ has covered that topic far better elsewhere.
The Island of Dr Hibbert is one of those segments that always stuck out in my mind growing up, but no-one else seemed to remember all that fondly. What I find funniest about this is how deliberately oblivious they play all of the characters, especially Homer. It might be pretty obvious writing, but I still find it funny that all of this clearly suspicious stuff is going on around then and Homer seems to meet it with willful ignorance, asking instead about timeshares. The animal thing is a bit of a weird gimmick, but they get some good jokes out of it and know when to call it quits. It rounds out an episode that might not be totally incredible but is definitely worth a rewatch.
9 – Treehouse of Horror VIII
Original Airdate: 26th October 1997
Segments: The HΩmega Man; Fly vs Fly; Easy-Bake Coven
The HΩmega Man is definitely the best segment of this episode. The set-up is dumb, but they throw in enough good jokes along the way that I’m willing to overlook the problems. Sure, Homer becomes a selfish arsehole the moment he realised he’s the last man alive, but let’s be honest here, you would, wouldn’t you? I know I would. They even managed to make Homer grieving over his family funny with the baseball bat joke. Overall, a super memorable segment that you should definitely seek out.
Fly vs Fly is just as funny, if a little less memorable. The yard-sale at the start was a good way to cram some quickfire jokes into minimal space, all of which land. I’d even argue this is the funniest Professor Frink has ever been. The transporter opens the door for another round of quickfire jokes which are even funnier than the first set. Marge telling Homer off for using it to pee will always make me giggle. The stuff with Bart and the fly is the weakest part of it, but even that has some good jokes, leading up to the final joke of Homer chasing Bart with the axe, which I think may be the funniest joke in the whole thing.
Easy-Bake Coven is a lot weaker in my eyes, but the strength of the other two segments is what keeps the episode on the list. There are some funny jokes at the start about the Salem witch trials, but it loses me after that. It’s not a bad segment by any stretch of the imagination, I just don’t think the ‘candy instead of children’ punchline is all that interesting. You should still go back and watch this episode, but maybe skip this last segment if you’re short on time.
8 – Treehouse of Horror I
Original Airdate: 25th October 1990
Segments: Bad Dream House; Hungry are the Damned; The Raven
Bad Dream House is a segment that seems to have been largely forgotten compared to the other two, but it’s definitely still a very good segment. It has fewer out-right jokes than we’re used to in these episodes, instead choosing some subtle warpings of the ‘haunted house’ formula to bring the laughs, something it does to great success. Something like Marge scolding the house like it was a misbehaving child is just a really funny joke that plays to the strength of the characters.
Hungry are the Damned is far and away the funniest segment of the episode, with a whole bunch of iconic jokes thrown in there. Homer needing two tractor beams to pull him up, the ominous double-talk of the aliens, the bit with the space dust on the ‘How to Cook Humans’ book, all of them are hilarious jokes that don’t lose any of their sting on a rewatch. Given that after this, the aliens would be mostly relegated to cameo roles, this is a solid segment to introduce them in. It understands the stereotypes and how to subvert them perfectly to great comedic effect.
The Raven is an odd one. I wouldn’t say it’s at all funny, which is what I want from a Treehouse of Horror episode, but it’s undeniably iconic. Sure, it’s essentially just an animatic of an Edgar Alan Poe poem, but A) It’s the only reason I ever learnt of the poem in the first place and B) It’s really good. While it does throw in comedic tones with Bart complaining about how unscary it seems in the modern-day, the animation used to tell the story is quite beautiful. It’s able to capture the dark and ominous mood of the poem, while still throwing in some comedic beats with how Homer and the raven move and act. It’s an oddity compared to everything else in this series, but it’s quite a pleasant one.
7 – Treehouse of Horror IX
Original Airdate: 29th October 1998
Segments: Hell Toupée; The Terror of Tiny Toon; Starship Poopers
Hell Toupée is the kind of segment that I never remember, but always enjoy whenever I see it. Snake is a character with so much untapped comedic potential. Even his spotlight episode(s) don’t really make the most of what this character has to offer, and I think this is the closest her ever got. We get some classic Chief Wiggum jokes right at the start, alongside the world’s double-standard when it comes to smoking. From there it’s a lot of murder-humour and visual gags, which aren’t my favourite, but I still find them funny here. I don’t know why it doesn’t stick in my mind very much, but it’s still worth seeking out.
The Terror of Tiny Toon, to the contrary, is one of the most memorable segments the show has ever done. Despite being a cartoon, The Simpsons odes it’s best to stick to fairly realistic rules (at least during this era of the show), so removing those restraints was a great move. The writers have used Itchy & Scratchy to take the piss out of kids cartoons before, but this was a step up. Actually taking us into that world, we see not only a deep understanding of what made cartoons like Tom & Jerry funny, but also a clear love from the animators for their style. It comes across as a love letter to those old cartoons, and it really funny to boot.
Starship Poopers is a bit of weird segment because, by all rights, I feel like it shouldn’t work, but it just does. Homer is what makes it to me. The alien stuff is funny, but it’s been done better before or since. Homer’s initial obliviousness to the situations (“Maggie lost her baby legs!”) followed by his righteous indignation is excellent stuff. The Jerry Springer scene is definitely the highlight, he plays a ridiculous kind of straight man that gives a good parody of those types of shows. You could argue those jokes have long since been played out, but I still get something out of them.
6 – Treehouse of Horror XX
Original Airdate: 18th October 2009
Segments: Dial ‘M’ for Murder or Press ‘#’ to Return to Main Menu; Don’t Have a Cow, Mankind; There’s No Business Like Moe Business
As the most recent entry on this list, it’s rare to see such brilliant episodes come out of the later seasons. Yet, for this one, they managed to nail it.
Dial ‘M’ for Murder or Press’#’ to Return to Main Menu, is an excellent parody of Hitchcock films (even if I don’t know a huge amount about them) while still standing up as a funny segment, even if you don’t know anything about the source material. The “Criss-Cross” joke might be a bit simplistic, but it gets a giggle out of me every time. The tenseness in the music compared to the juvenile actions on the screen give the whole thing a wonderfully comedic tone, and even the way Lisa ends up killing Bart is funny.
Don’t Have a Cow, Mankind, is a segment that has remained fresh in my mind ever since I first saw, and I’m not entirely sure why. The Simpsons have done zombie parodies before, but they made sure to do this one differently to before. It feels like they’re breaking out to tread new ground rather than imitating their greatest hits. The idea of the burger-squared is so stupid that I can’t help but laugh, and there’s something ironically funny about what it does to people. It’s definitely not very smart humour, but it’s still done in a way that I find funny. Just about everything Apu does, for example, gets a giggle out of me, even though they are fairly obvious jokes.
There’s No Business Like Moe Business is utter genius writing. Not only does it have a strong sense of plot where jokes are crammed in at every opportunity, but it expands the scope to that of a stage play, and makes a bunch of meta-jokes about theatre, all of which are brilliant. Stuff like Homer’s makeup not being ready in time, so Moe has to stall; the set being incredibly janky or anything any of the audience members had to say was laugh-out-loud funny. Then, of course, there are the musical pieces which give the whole thing a fun tone that translates so well with the jokes being told. It’s one of those segments that I firmly believe that had it been in one of the early seasons, would be seen today as an all-time classic.
5 – Treehouse of Horror VI
Original Airdate: 29th October 1995
Segments: Attack of the 50-Foot Eyesores; Nightmare on Evergreen Terrace; Homer³
Attack of the 50-Foot Eyesores is one of the weaker segments on this list. It’s very plot-heavy, and many of the jokes are visual gags of the monsters destroying stuff, which is fine, but it’s not really for me. There is still a bunch of funny stuff in there though. Homer’s non-reaction to the whole situation is out of character for him in one of the funniest ways possible. At the same time, the solution of creating a catchy jingle is a surprisingly intelligent and accurate takedown of the advertisement industry. This is a good segment, but it’s definitely not the main reason to watch this one.
Nightmare on Evergreen Terrace is most certainly one of the main reasons to watch this episode. As easily one of the show’s most easily comedic characters, Willie is a great villain in this one. He’s violent and savage-looking enough for it to be believable, while his character comes with an inherent patheticness that makes so many of his jokes work. The backstory scene is easily the highlight here. We’ve got “Do not touch Willie”, the Smarch joke and the taking turns to speak joke. The fight at the end isn’t all that interesting, but they still throw in a bunch of jokes to keep us going until the end, even managing to take the piss out of the ‘killer isn’t actually dead’ trope of horror films.
Homer³ is easily the most memorable segment on this list, purely because of how different it looks. Even before the 3D stuff happens, we get some brilliant jokes as Homer make a mad dash to find a hiding spot. Then, we get to the 3D world and hilarity ensues. Homer’s reaction to seeing his ass in 3D for the first time is brilliant, and the meta-joke about how expensive the 3D area is one of my favourites. We get a quick cascade of secondary characters in to try and solve the problem, and finally, we top the whole thing off with a trip to the real world. It’s got plenty of amusing moments throughout, along with being a genuinely iconic moment in Simpsons’ history.
4 – Treehouse of Horror IV
Original Airdate: 28th October 1993
Segments: The Devil and Homer Simpson; Terror at 5 & 1/2 Feet; Bart Simpson’s Dracula
The Devil and Homer Simpson is one of the all-time great segments. Flanders as a cheery version of the devil is utterly hilarious, and Homer’s interaction with him is perfect. It’s the kind of segment where all I can really do to describe it’s greatness is list jokes. Jokes such as: Homer claiming to be smarter than the devil; Homer eating all the doughnuts in the world; THE TRIAL SCENE. It’s a Treehouse of Horror segment with Lionel Hutz in it for God sake, it’s just brilliant. It doesn’t try to do anything overcomplicated, it just creates a simple premise and stuffs it to the brim with hilarious jokes.
Terror at 5 & 1/2 Feet, on the other hand, is one of those segments I never really got. There still some great jokes in there, don’t get me wrong, pretty much anything Skinner has to say is worth watching the whole thing, but other than that, I just find it a bit uncomfortable. I don’t know why, because I’ve never been in this situation, but the idea of desperately pleading with someone to believe you, only for everyone to think you’re crazy is just quite distressing to me. I still enjoy this segment, but it comes with a bit of baggage I can never cast from my mind.
Bart Simpson’s Dracula is another one of the greats. Burns being evil is always comedy gold, and now we get to throw some vampire humour over the top of it. Once again, the family’s complete obliviousness of the danger of the situation is an extremely fertile ground for jokes, and it’s used to its full potential. Other than that, once again, it’s just a list of hilarious jokes. Grampa wanting to kill the boy; the super happy fun slide, and the fact that the whole thing ends on a Christmas carol. I know they’d pull this joke out too many times in the later seasons, but this was the first time they did it, and it was still funny.
3 – Treehouse of Horror VII
Original Airdate: 27th October 1996
Segments: The Thing and I; The Genesis Tub; Citizen Kang
The Thing and I is prime Simpsons’ Halloween material. It gives us an actual mystery that feels like it pays off, before turning into a tense action scene and shoving as many funny jokes as possible along the way. Homer & Marge’s suspicious acting is ripe for comedy and the kid’s insistence on knowing what’s going on plays of it great. The over-curiousness that we all know children can have is played for laughs in an amusing way that still serves the further the mystery. The resolution & ending is classic stuff too. The “left twin” always being evil, the revelation that it was actually Bart the whole time, and then the flipping of the scenario to end things off. It’s tense, it’s funny, and it’s an absolute classic.
The Genesis Tub was the segment I always remember liking the most as a kid. I don’t know why, but something about the premise really appealed to my child-self. We get plenty of funny interactions between Bart & Lisa, with Lisa eventually having the kind of funny moments we don’t often get from her. Her delight at creating Lutherans, or the indignation with which she treats Bart. They even manage to squeeze in a completely irrelevant joke about a waffle iron and make it hilarious. Lisa very rarely gets a chance to shine in the Halloween segments, her character doesn’t really fit with their tone, but this was the perfect way to make use of her.
Citizen Kang is another all-time classic. Homer rules the roost in this one, and he shines like you wouldn’t believe. His determined, but utterly incompetent, drive to stop the aliens makes for all kinds of hilarious moments, and this is where the aliens get all the chance in the world to shine. Their misunderstanding of Earth culture and the ease with which they sway the masses is funny in a way that feels oddly more relevant in the modern-day. Then, the final gag about it being a two-party system is some really on-the-nose satire that is as funny as it is depressing. Then, of course, we cap things off with the iconic line “Don’t blame me, I voted for Kodos,” which sums up politics better than years of satirical cartoons ever could.
2 – Treehouse of Horror III
Original Airdate: 29th October 1992
Segments: Clown Without Pity; King Homer; Dial ‘Z’ for Zombie
Clown Without Pity brings the laughs in all the right places. Homer at the evil store is a hilarious scene, featuring the “That’s good, that’s bad” bit, which is genuinely one of the most well-structured jokes I’ve ever heard. The rest of the segment isn’t quite as funny, but they still get a lot of good jokes from the doll trying to kill Homer, and Homer trying not to die. Then, the thing wraps up in another great joke with the doll’s switch being set to evil.
King Homer is the second-best film parody the show has ever done. As where the Godzilla parody that I talked about in the ‘worst’ list took the easy way out with its jokes – taking some outdated shots about Japanese films & then swerving into a Hollywood satire – this one is a lot more clever with what it does. For one thing, it’s a lot more faithful to the source material and actually commits to the bit. For another, instead of making wide-stretching jokes about the film industry, it relies on the characters to do the heavy lifting. Things like Smithers saying that “women and sea-men don’t mix” or Marge finding King Homer’s oafishness weirdly attractive is the kind of character-based humour that the show is brilliant at and should always be at the core of the writing.
Dial ‘Z’ for Zombie is just a 7-minute long list of great jokes. There’s technically a plot, but after about 2 minutes it ceases to matter and is just a vehicle to get the characters to places where we can make jokes. Sure, it’s not a super-strong segment, but when you’ve got jokes like Homer shooting Flanders, Zombie Shakespear and anything Bart does, who cares? It’s hilarious, and that’s all that matters.
1 – Treehouse of Horror V
Original Airdate: 30th October 1994
Segments: The Shinning; Time and Punishment; Nightmare Cafeteria
Let’s be honest, there was never any question as to number 1.
The Shinning is not only the single best Treehouse of Horror segment, but it may also be the best thing The Simpsons have ever produced. For one thing, I really like The Shining, and this absolutely nails the parody aspects. So many of the jokes in this are absolutely iconic. The “all work and no play” bit, the “urge to kill bit” and anything Burns & Smithers have to say to one another. Ultimately, Homer is the star of the show in this one, and he’s perfect as the Nicholson character that slowly goes crazy, with just the right amount of Homer oafishness mixed in. However, the other characters are on great form too. Marge, Burns, Smithers, Willie, even Chief Wiggum all have some of their best jokes in this segment. It really is an all-time classic.
Time and Punishment takes us from the best segment of all time to the second-best. Homer once again dominates the segment and brings an endless string of laughs. The pacing is excellent and makes the 7-minute long segment feel like a fully fleshed out episode of the show. Homer’s visits to the past serve not only to break up the action but also give us a brief insight into Homer’s deteriorating mental state. Then, the alternate dimensions that Homer visits all have something hilarious to offer us. The longer sections like the Flanders’ universe and the perfect universe are broken up by quick little looks into ones like the giant universe, or the one where Willie knows. It makes the most of its concept and packs it with as many jokes as possible, leaving it to stick in the mind forever.
Nightmare Cafeteria is the weakest segment of this episode, but it’s still top 5 of all-time levels. Firstly, it’s genuinely quite creepy. The glee with which the teachers seem to consume the segments is disturbing, especially when combined with how weird they look as fat-slobs. While this is technically a segment about the kids, Skinner is undoubtedly the MVP when it comes to bringing the funny, with how calmly he tells the teacher about cooking Jimbo, or the big rant about Uter. Outside of that, we get the payoff to the running joke of all three segments, with Willie failing to save the day. Then the whole episode wraps up with that inside-out gas segment which I find really uncomfortable to watch, but it’s still funny in that kind of way.
To put it simply, Treehouse of Horror V is the only instalment in the series that I think is flawless and easily ranks as one of the best Simpsons episodes of all time.
And there you have it! Thank you very much for taking the time to read this. Please, let me know what your favourite Treehouse of Horror episodes/segments are, either in the comments below or on Twitter @10ryawoo. Finally, make sure you come back here this time next Friday, where I’ll be covering AEW’s Full Gear Pay-Per-View!