The start of the spooky Halloween season is a great time to be a fan of The Simpsonsand it’s the best time to go back through some of its major classics released over the decades. Each season of the show (after the very first) has helped to celebrate Halloween over the years with a special episode set outside of the main continuity. These specials ratchet up the stakes as characters can die, new horrors arrive at every turn, movies are parodied, and most importantly there are tons of laugh to be had throughout it all with this wacky family.
The Simpsons kicked off their soon to be annual tradition of launching a new Halloween special during the second season, and through this initial “The Simpsons Halloween Special” era (before they took on their full Treehouse of Horror nickname in the years after) fans got to see some of the strongest holiday specials the show has ever offered. It’s going to be tough to rank them all on a whole as there are lots of splitting hairs to separate the weakest from the strongest (as some segments are stronger than others), but read on for our choices of the strongest from the first ten seasons of Treehouse of Horror episodes.
9). Treehouse of Horror IX
Coming during the tenth season, Treehouse of Horror IX felt like the start of a different era for The Simpsons. Its three segments were still strong by Treehouse of Horror specials as “Hell Toupee” gave Homer a fun and murderous makeover (and was jam packed with gags), and “The Terror of Tiny Toon” brought Bart and Lisa into the world of Itchy and Scratchy. But “Starship Poopers” was a the first sign of a decline of that larger focus on Horror for a while. This third segment has fun ideas of its own (“Maggie lost her baby legs!”), but its reliance on the Jerry Springer cameo and full tribute segment really does unfortunately date it compared to some of the other classics on this list.
On top of the other specials not being as full of darker Horror elements as some of the others on this list, Treehouse of Horror IX unfortunately lands at the bottom. But it’s nothing to scoff at either as this is a strong line up competing for places here.
8). Treehouse of Horror VII
There are quite a few fun character jokes to be found in this year’s edition, and that’s the case with both “The Thing and I” (which introduces Bart’s secret twin Hugo) and “The Genesis Tub” (which sees Lisa creating a tiny world). These two shorts are nowhere near as strong as “Citizen Kang” when it comes to their central premises and jokes, however, so you kind of have to judge Treehouse of Horror VII on the strength of its best short. Unfortunately, timelessness is a key factor to any truly great Treehouse of Horror special, and that’s going to be the biggest factor holding this one back.
“Citizen Kang” approaches a sense of timelessness with its idea of space aliens replacing politicians and taking over the United States, but because so much of it anchors on the knowledge of then current presidential candidates Bill Clinton and Bob Dole, it stays within the 1990s. Not even the strength of those jokes can compare to some of the other specials that can still hit hard no matter what year or context you watch them in.
7). Treehouse of Horror II
The Simpsons’ second ever Halloween special kept experimenting with the way the show told its stories, and so it’s fairly unique when stacked against the others. Deciding to instead follow Lisa, Bart and Homer as they have bad nightmares after eating too much candy, it leads to some rather fun segments. Lisa dreams of a monkey’s paw, Bart has a Twilight Zone-esque dream where he has the powers to bend reality, and Homer’s turns him into a robot. While none of the segments are downright “scary” compared to even the first special or everything that came after, what ultimately holds this one back is that it feels kind of dry.
It’s still got a ton of jokes that you’ll be surprised to hear for the first time here (like “He’s got a board with a nail in it”), and it’s got a timelessness to its ideas that still make it stand out from the pack. But it also seems fairly subdued in just how far it’s willing to go with its ideas. It almost seems tame with its terror compared to what we had seen before (and what we’ll seem after), and thus just feels slower than most.
6). Treehouse of Horror VIII
Treehouse of Horror VIII starts off with a bang in comparison as the show pokes fun at censors of its violent content by brutally killing a censor on screen. Then the episode follows through on that promise with “The Homega Man” (which is a parody of the horror classic, “The Omega Man”) that sees Homer surviving alone in a nuclear apocalypse, “Fly vs. Fly” that fuses Bart to a fly’s body, and “Easy-Bake Coven” which turns Marge into a witch. Not only does this special pack tons of ghoulish imagery, but it’s definitely packed with memorable scenes and jokes.
“Fly vs. Fly” alone has everything with the teleporter, “The Homega Man’s” initial Homer reaction to the world being destroyed (as “Little Marge” strikes out at baseball), and “Easy-Bake Coven” is the story of the very first caramel cod, after all. These jokes and parodies aged very well in retrospect, and even work when you don’t know the source material. It’s all bangers.
5). Treehouse of Horror III
Treehouse of Horror III continued with the early Halloween specials’ trend of finding a fun story to unite its anthology, and is set during a Halloween party that goes wrong. It not only has lots of fun sight gags as we get to see everyone’s costumes, but it leads to some fun set ups for each of the stories too. “Clown Without Pity” is the surprising origin of Homer’s “That’s Good!,” and also sets a trend for the episode where we’ll see hilarious hearts and a different tone from the other Halloween specials.
“King Homer” is just a straight King Kong parody, but really makes the most out of the idea with how willing it is to kill off fan-favorite characters for quick gags. But it’s “Dial Z for Zombies” that really stands out after all this time. This short alone is worth the price of admission, and is honestly one of the best aged shorts in The Simpsons‘ long history of Horror. It’s just one hilarious moment after another (“He was a zombie?” “John Smith, 1882?”), and filled with genuine terror as many people die before it comes to an end.
4). Treehouse of Horror VI
This is probably going to be the most controversial choice here, but there’s really no way you can argue against the strength of “Homer3” Treehouse of Horror VI had a lot of fun jokes with “Attack of the 50 Foot Eyesores” (like Paul Anka’s guest spot saving the day), and had a truly scary parody of A Nightmare on Elm Street with “Nightmare on Evergreen Terrace” (as Groundskeeper Willie’s burning skeleton is legitimately a gruesome moment), but “Homer3” is likely going to be what fans remember the most as it was The Simpsons first foray into the third dimension.
Inspired by the classic The Twilight Zone episode “Little Girl Lost,” this segment saw Homer escaping into a wild CG animated world and introduced a whole generation of animation fans to the then popular technology at the time. This was the first special in a long time that felt like a true event for The Simpsons as it offered something you weren’t going to get in a regular week. The quality of that animation itself may or may not have aged well depending on who you ask, but it was mind blowing at the time.
3). Treehouse of Horror IV
Treehouse of Horror IV is both strong when it comes to its Horror elements, but also incredible when it comes to its comedy. “The Devil and Homer Simpson” gives fans Ned Flanders as the devil and that incredible sequence of Homer being sent to Hell (which is filled with tons of gruesome yet hilarious imagery), “Terror at 5 1/2 Feet” has that brutal beheading of Ned, and then of course, “Bart Simpson’s Dracula” is just peak Halloween special. It’s got everything you want from a Treehouse of Horror episode.
Three segments that might parody other movies or shows, but you don’t need knowledge of them to enjoy it. Each one stands on its own, and are further enhanced if you know the references. Even without them, it’s got some very high stakes for every character as death is pretty much imminent throughout each segment. And it all ends with a bang as “Bart Simpson’s Dracula” is so jam-packed with jokes in such a short runtime that you can look at any minute long section of it and find multiple hits.
2). Treehouse of Horror
To this day, however, The Simpsons can rest easy knowing that their very first Halloween special continues to be one of the best. Not only does it have parodies of other Horror or science fiction media, but it remains timeless without any of the risk of being dry like some of the earlier segments can have. There’s just an incredible creative energy here on full display from everything around it. As Bart and Lisa tell scary stories in the treehouse, fans are treated to three different notably terrifying tales.
“Bad Dream House” takes on haunted house films, “Hungry are the Damned” took on the famous “To Serve Man” sci-fi story, and “The Raven” was a full retelling of Edgar Allen Poe’s famous poem with James Earl Jones popping up throughout the special’s segments before bringing the poem to life. It’s a special that has aged incredibly well, and even brings a level of understanding to The Raven that would bridge the gap between generations. It launched a yearly tradition for a reason.
1). Treehouse of Horror V
Even with all of this competition, however, Treehouse of Horror V is the greatest overall special of these first ten seasons. It’s got the timelessness you crave with its stories, it has a movie parody, a science fiction story, and a nightmare inducing one, and it all comes together in one of the strongest full packages of this era. It starts incredibly strong with “The Shinning” (a parody of Stephen King’s The Shining) that is really non-stop jokes as soon as Homer starts to lose his mind (“No TV and no beer make Homer something something”).
Then it continues with the gags seen in “Time and Punishment” (“Donut? What’s a donut?” and then “Nightmare Cafeteria” went truly dark and scary by killing off the show’s children in gruesome ways. This year was almost a response to complaints seen before as all of these dark and violent elements had been ratcheted up, and it’s got some images that are downright gross in that best Horror way. It ends with the family dog eyeing Bart’s intestine after all, so there’s nothing more you can ask from a Simpsons Halloween special of this first era.
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