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Few pieces of media from the 1990s are as revered or as widely known as The Simpsons. At the show’s peak, from 1991 to around 2003, some of the show’s best episodes were their Halloween specials, which were given the moniker: Treehouse of Horror. In honor of the spooky Halloween season, we will be counting down thirteen of the best segments from these specials—one for each season of The Simpsons worth watching. 

13. “The Raven”

The first few seasons of The Simpsons tend to be hit or miss. It is easy to tell that Matt Groening and the writers of the show are still figuring out the comedic and artistic style that would define its best seasons. This segment, “The Raven,” from the first Treehouse of Horror special and the show’s second season is among the most interesting things to come from its early years. Adapted from Poe and full of artistic flourishes and the booming voice of James Earl Jones, it really is a sight to behold.

Image from GIPHY

12. “Clown Without Pity”

This segment from the fourth season begins with Homer forgetting to get Bart a present for his birthday. As the dutiful father Homer has proven himself to be time and time again, he immediately turns to the House of Evils, “Your One Stop Evil Shop,” to get Bart something he will truly cherish. Homer, of course, chooses a cursed Krusty the Clown doll for his son. 

Treehouse of Horror segments tend to vary between being either sardonically ironic or surprisingly horrifying in how they make the audience feel dissociated from reality. This episode lands firmly on the lighter end of this spectrum.

Image from Tumblr

11. “Hungry are the Damned”

Appearing right before “The Raven,” this segment sees the Simpson family beamed up into a flying saucer piloted by the aliens Kang and Kodos. Of the segments in the first Treehouse of Horror, this one is by far the funniest to watch. While entertaining in its own right, it is probably best known as the segment that introduced Kang and Kodos to the show’s canon.

Image from GIPHY

10. “Island of Doctor Hibbert”

“Think what Shakespeare might have accomplished if he’d had the eyes of an eagle, or could spray stink on his critics!” Oh what might have been. The second segment on this list to be adapted from another work, this one adapts “The Island of Doctor Moreau” by H. G. Wells. The Doctor Moreau, in this case, is the show’s favorite cackling doctor, Dr. Hibbert. It is probably one of his best moments in the show. Plus, you get to see Homer as an anthropomorphic walrus, so win, win.

Image from MakeAGIF

9. “Fly Vs. Fly”

Clearly inspired by David Cronenberg’s 1986 remake of The Fly, this segment sees Bart exclaim “I’d be stupid not to do this!” before splicing his DNA with an insect. This, of course, does not produce a Bart with the best of both himself and his insect compadre, but instead plants Bart’s head onto the tiny body of a fly. This ironic turn of events is, supposedly, what happens when someone trifles with primal forces of nature. Who knew?

Image from Tumblr

8. “The Thing and I”

“…So we did the only humane thing.”

“We chained Hugo up in the attic like an animal and fed him a bucket of fish heads once a week.”

Oh Homer, the most loving and caring of all parents. This segment contains the reveal that Bart has a conjoined twin separated at birth: the supposedly evil, Hugo. Except, actually, Bart is the evil twin. Like “The Island of Dr. Hibbert” before it, this segment features a highlight performance by the cackling and careless Doctor Hibbert, who is always a delight when he appears in these specials. 

Image from Imgur

7. “The Devil and Homer Simpson”

This segment sees Homer make the informed and wise decision to sell his soul for a donut. This inevitably ends up in a trial for Homer’s soul. Some highlights of this episode include seeing Flanders as the Devil, complete with red cape, horns, and the feet of a Satyr. He has Homer’s face metamorphosized into a donut—which he, of course, cannot resist eating. 

Image from GIPHY

6. “Night of the Dolphin”

“Bottlenose bruises, blowhole burns, flipper prints; this looks like the work of ratty teens. Lou cancel the Prom!”

This segment sees the town of Springfield invaded by an army of killer dolphins. Treehouse of Horror sees The Simpsons at perhaps their most creative and artistic, possibly leading to several of their best written episodes. The next five segments in particular contain many of the best and most memorable moments of the show. This segment, however, is not one of these. This episode is purely dumb fun. A ridiculous idea taken to a ridiculous extent. There is something endlessly entertaining about watching a dolphin body slam Apu Nahasapeemapetilon to the ground and slap him with its muscular cetacean flipper. “Help!” Apu screams, but there is no help. The dolphins are here, and they’ve already won.

Image from Tumblr

5. “Nightmare Cafeteria”

This segment is a great representative of these specials as a whole. Like many of the best episodes of this show, it features Bart and Lisa Simpson discovering something truly terrifying. In this case, their teachers have begun to cook and eat their students. This, of course, raises no alarm from their mother, who tells them: “March right back to that school, look at them straight in the eye, and say, ‘Don’t eat me.’” One must wonder if that trick would’ve worked for that guard who gets tongue bit off by Hannibal Lecter in Silence of the Lambs.

Image from SYFY

4. “The Genesis Tub”

“Oh boy, mold! That’s Science Fair pay dirt!”

In this segment, Lisa accidentally creates life while conducting a science experiment to prove the dangers of soft drinks on our teeth. These little lifeforms eventually develop enough to beam Lisa down to see their little world, where she learns that they see her as their God. One really must wonder whether Matt Groening imagines this a lot since this segment is incredibly similar to the excellent Futurama episode: “Godfellas.”

Image from FandomFactory

3. “Homer³” (“Homer Cubed”)

Okay, here’s the deal: this segment is absolutely terrifying. It brings to mind the kind of horror that permeates the Spongebob Squarepants episode “SB-129,” where Squidward goes so far into the future that nothing exists but an empty realm of words and thoughts that he can’t escape. In this segment, Homer finds himself in a very similar “Third Dimension,” full of abstract shapes and objects. Homer can be heard in his home, but they are nearly powerless in being able to help him, leaving him isolated in this uncaring and strange reality. There are other Treehouse of Horror segments that scared me as a child, but nothing really comes close to this. 

Image from Simpsons Wiki

2. “Time and Punishment”

This segment begins with Homer jamming his hand in the family toaster not once, but twice. He is then sent hurling back in time to the Mesozoic era, the time of the dinosaurs.  Homer remembers the helpful advice his father gave him on his wedding day: “If you ever travel back in time, don’t step on anything! Because even the tiniest change can alter the future in ways you can’t imagine!” Homer then proceeds to immediately squash a bug and alter the future.

This segment is amazing in the sheer variety of different locales it contains. One minute Homer is in a future where Flanders has become the overlord of the world and forces his subjects to get lobotomies and submit to his will, and the next Homer is in a future where it rains donuts from the sky instead of rain.

Image from GIFER

1. “The Shinning”

Ah, here it is. The proud and “shining” achievement of the Treehouse of Horror. It probably isn’t possible for there to be a better and more iconic parody of Stanley Kubrick’s The Shining. Almost every scene and beat from this segment is endlessly quotable. It’s even mildly unnerving, though without the same existential dread as “Homer Cubed.” The comedy of “The Shinning” is the real highlight here. It moves at an excellent pace, with virtually no time wasted. Even though it follows Stanley Kubrick’s film almost beat for beat, the comedic delivery is timeless enough that having seen the original film is not a requirement.  This is quite possibly the best The Simpsons ever was, both as a show satirizing pop culture and as a comedy in its own right.

Image from Tumblr

Well, there it is folks. These specials were the best The Simpsons ever was, and certainly better than anything it ever will be again. Have a goofy and spooky Halloween!

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Sources: GIPHY, Tumblr, MakeAGIF, Imgur, SYFY, FandomFactory, Simpsons Wiki, GIFER

Images: GIPHY, Tumblr, MakeAGIF, Imgur, SYFY, FandomFactory, Simpsons Wiki, GIFER

Featured Image: Simpsons Wiki

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