The Simpsons is one of the longest-running TV shows in history, and while the animated FOX series has always tried to shake things up, it does keep one tradition alive: a yearly Halloween episode. But while these tend to be some of the funniest episodes each season, some segments are better than others. So we decided to pick out our favourite 13 (because it’s a creepy number or whatever) and highlight the best “Treehouse of Horror” segments in the show’s entire history.
One episode that won’t be on this list — even though it’s one of the best Simpsons episodes of the last 15 years — is “Halloween of Horror.” While it is a Halloween-themed episode of The Simpsons, it’s not a traditional multi-segment Treehouse of Horror special. So it doesn’t count.
Anyway, with that out of the way, here are the 13 best Simpsons Treehouse of Horror segments in no particular order.
King Homer (Season 4, “Treehouse of Horror III”)
I always love when The Simpsons swings for the fences with its parodies and ideas, even better if it hits a home run. And King Homer is indeed a homer. (Get it?) Anyway, making a condensed black-and-white parody of the original King Kong starring Homer as the ape and Marge as his human crush is funny, clever, and a perfect translation of these two characters. And let’s not forget how funny Mr. Burns is in this.
Easy-Bake Coven (Season 9, “Treehouse of Horror VIII”)
Many of the best Treehouse of Horror segments aren’t directly connected to Halloween, oddly enough. But “Easy-Bake Coven” is a great example of how the show and its writers can take classic trappings of Halloween, like witches, and twist them into comedy gold. It also helps that this episode is hilarious, with some very good jokes, like Wiggum becoming a giant hamster or the bit involving the Flanders’ sexless marriage.
Bart Simpson’s Dracula (Season 5, “Treehouse of Horror IV”)
It almost feels like cheating to reward The Simpsons’ writers for turning Mr. Burns into Dracula. It’s such an obvious idea. And yet, it works and leads to one funniest (and weirdest) Treehouse segments ever. I mean this segment has the Dracula cape joke, Homer saying “Pennsylvaniaaaaaaa,” and the intercom joke where Burns inadvertently reveals his whole nefarious plan because he accidentally held a button down. And all of that just in the first 90 seconds.
Citizen Kang (Season 8, “Treehouse of Horror VII”)
Ask anyone in the U.S.: American politics are truly terrifying. So it makes perfect sense for the show to use the 1996 presidential election as fodder for a fantastically funny Halloween segment featuring aliens, abductions, and jokes about our two-party system. And if you have a problem seeing this segment on the list, don’t yell at me; I voted for Kodos.
The Shinning (Season 6, “Treehouse of Horror V”)
Raise your hand if, as a kid, this was your first exposure to The Shining, rather than the iconic Kubrick film or the original Stephen King book. Don’t worry, you’re not alone. I know a lot of people, myself included, who saw this segment first. And it’s a testament to how funny and well-written this short is that it still works perfectly even if you’ve never seen the source material.
A haunted elevator pouring out a giant wave of blood on the wrong floor and Mr. Burns commenting on how odd that is, “Usually the blood gets off at the second floor”? Still funny, even if you’ve never glimpsed the original scene.
The Devil and Homer Simpson (Season 5, “Treehouse of Horror IV”)
Technically this is all unranked, but if I were ranking them, “The Devil and Homer Simpson” would likely be at the top. Homer selling his soul to the devil — who knows Bart personally and looks like Flanders — is a great concept, and the writers perfectly wring out every drop of humour. I quote this segment more often than I care to admit and the bit with Homer chomping away on endless doughnuts in Hell is one of the funniest visual gags in the show’s history. All that, plus a heartwarming ending and a wild twist with a killer final joke! What a segment!
Time and Punishment (Season 6, “Treehouse of Horror V”)
Homer Simpson travelling through time and seeing alternate futures is very funny. Some stand-out bits include the part where we see a parallel world where Flanders is in control of everything and another where the only difference is that doughnuts fall from the sky like rain. (But only after Homer has already left.) However, I also must mention the opening of this segment featuring Homer and a toaster. It’s one of the most random moments in the show’s history, and his screams always make me laugh. A perfect way to kick things off.
It’s the Grand Pumpkin, Milhouse (Season 20, “Treehouse of Horror XIX”)
Yes, a Season 20 episode made the cut. Modern Treehouse of Horror segments often feel like lazy parodies, or move too fast to stick with you. But this one — a wonderfully animated parody of Charlie Brown cartoons — is the exception to the usual meh Treehouses of the show’s later years. Millhouse is the perfect stand-in for Linus. Then having the Grand Pumpkin show up, only to become filled with homicidal rage over all the pumpkins we butcher in October, is a silly and murderous twist on Charlie Brown that makes me laugh every time I watch it.
Clown Without Pity (Season 4, “Treehouse of Horror III”)
A Krusty the Clown doll becoming evil and then trying to kill Homer is both actually a bit scary, especially as a younger viewer, and also a very funny setup for a short Halloween segment. However, most people remember this episode for a very different reason: the bit between Homer and a mysterious salesman who sells forbidden objects from places men fear to tread, and also offers frozen yogurt. (He calls it “frogurt.”)
Homer3 (Season 7, “Treehouse of Horror VI”)
It may not be the funniest or scariest Treehouse of Horror segment in Simpsons history, but this short still deserves praise because of its incredible 3D animation. Yes, today it looks very primitive, but at the time it was groundbreaking stuff, especially for a TV show. And because the CGI company that handled it was so desperate for more Hollywood work, it reportedly ended up doing the job for only $US6,000 ($8,329).
Terror at 5½ Feet (Season 5, “Treehouse of Horror IV”)
Oh hey look, it’s another segment from Season 5’s Treehouse of Horror, meaning all three segments made my faves. Impressive! Anyway, it’s not surprising that what is considered to be one of the best seasons of the show produced a great Treehouse of Horror special.
And “Terror At 5½ Feet” is a wonderful way to open the episode, with Bart recreating the classic Twilight Zone episode as he panics about a creepy creature lurking on the outside of the school bus. As a kid, I remember this segment genuinely making me a bit scared, especially that twist (and shocking) ending.
Nightmare on Evergreen Terrace (Season 7, “Treehouse of Horror VI”)
Groundskeeper Willie being twisted into Freddy Kruger is such a perfect use of the character that it seems wild it took the show seven seasons to finally do it. This episode is also surprisingly brutal, with kids like Martin getting violently murdered onscreen as Willie enters dreams and hunts down the kids whose parents let him burn during a PTA meeting. But in the parents’ defence: They all wanted to get out of there fast because it was a terrible, nasty Smarch evening.
Nightmare Cafeteria (Season 6, “Treehouse of Horror V”)
And here’s the third and final segment from season 6’s Treehouse of Horror episode, which means that it — like season 5’s Halloween special — is an all-time classic. What I appreciate about “Nightmare Cafeteria” is that it feels creepy and disturbing. It also has some great jokes, like Skinner’s “Isn’t there a little Uter in all of us?” and Willie trying to save the kids, but failing and dying for the third time in the half-hour.
And then, after Milhouse bites it in a giant blender, the segment ends and reveals it was all a dream. There was nothing to fear, well, except for that fog that turns people inside-out. Luckily, the Simpsons have high-quality windows, and…wait, I’m being handed a message. Oh no.
Of course, narrowing my picks down to just 13 great Halloween Simpsons segments means I had to cut some other great ones. And odds are at least some of you have a favourite that didn’t make the cut. If so, let me know which Simpsons Treehouse of Horror short is your favourite in the comments below.
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