I could go on endlessly about my deep love and appreciation for The Simpsons. It’s been said countless times that the show’s golden age, usually considered to be seasons 2-8, features probably the best comedy writing of all time. They contain some of the smartest joke-writing and satire, without sacrificing character, heart, and storytelling. The Simpsons is a an animated series so relatable and quotable, I’ve annoyed many people with how often I’ve used the phrase “This is like that episode of The Simpsons where…”

Now with the year’s most sacred of holidays, Halloween, approaching, I thought it’d be fun to sit back and reflect on my favorite Treehouse of Horror segments out of the shows 30+ seasons. It was hard to narrow down just five; however, after thinking about which episodes left the biggest impact, either by how clever or memorable they are, or how they literally made me laugh out loud every time I watch them, I think I can safely say that the following choices are easily my top five favorite episodes. 

Treehouse of Horror – Top 5 Picks

Voice Cast: Bart (Nancy Cartwright), Lisa (Yeardley Smith), Homer (Dan Castellaneta), Marge (Julia Kavner)

5) “The Thing and I” from Treehouse of Horror VII 

In this episode from season eight, Bart and Lisa hear strange noises coming from the attic. The pair soon find out Bart’s evil conjoined twin Hugo who was separated at birth is the source of all the ruckus. Bart and Lisa also discover that Homer and Marge have kept Hugo locked in the attic, feeding him fish heads once a week. “It saved our marriage,” Marge explains to them proudly. Soon, Hugo escapes and we learn of his true intentions — to rejoin himself with Bart.

Doing the most with a clichéd story, “The Thing and I” is a non-stop barrage of sight and sound gags that constantly top each other. From Hugo’s bizarre experiments, like the unforgettable “pigeon-rat” to a quick gag involving the unsold copies of Homer’s autobiographies. This episode is perfect for Halloween fun.

4) “The Raven” from Treehouse of Horror I This episode from the second season showcases The Simpsons’ ability to pay loving tribute to classic literature with startling accurate degree.

The plot of “The Raven” is straight-forward: it’s an adaptation of Edgar Allen Poe’s poem The Raven with James Earl Jones lending his incomparable voice as the narrator; Homer takes on the role as the poem’s protagonist; and Bart as the titular raven. 

What makes this segment so special is that it’s surprisingly one of the best adaptations of Poe’s most famous work. There’s no deviation as the episode follows the tale beat for beat, mixing it with some genuinely beautiful animation. The episode became unexpectedly chilling for The Simpsons due in large part to Jones’s excellent narration as well as Castellaneta’s somber performance as Homer.

While light on quips, “The Raven” goes to show how The Simpsons’  Treehouse of Horror can be more than just comedy and, when needed, can bring the horror and tension. If you’re a fan of the original poem, you owe it to yourself to seek this out and watch.

3) “The Devil and Homer Simpson” from Treehouse of Horror IV

What would happen if Homer sold his soul for a donut? Well, the results are comedy gold as shown in this segment from the fifth season Halloween special.

Desperate to get a donut, Homer offers to sell his soul to the devil, who is secretly Ned Flanders (voiced by Harry Shearer) this entire time. Homer soon regrets the exchange and tries to fight for his soul which leads to a courtroom battle; Homer as the defendant and the devil as the plaintiff. 

The premise itself is already funny, the visual of Ned as the devil alone leaves me in hysterics, but the segment finds a variety of ways to up the ante in humor. Some examples include Homer in hell being forced to eat all the donuts in the world as a form of punishment (which hilariously backfires); the late Phil Hartman guest-voicing as Lionel Hutz who is the worst attorney you can imagine; and finally, everything culminating in a resolution that’s befitting as well as gut-bustingly hilarious.

2) “Homer³” from Treehouse of Horror VI

Another Homer centric episode from the seventh season special, “Homer³”finds its namesake discovering a portal in the living room that takes him to the third dimension resulting in the show going to 3-D animation for the first time.

While “Homer³” can be written off as a gimmick to showcase CGI animation, this episode is one of the first mainstream uses of computer generated imaging, even predating Toy Story by a month. This episode is iconic as well as hilarious. With jokes poking fun of the high-production costs to Homer finally being able to see how overweight he is in 3-D; “Homer³” finds ways to be self-aware of the animation but never to an annoying degree. The final scene is probably one of the best, although I shan’t spoil it here for those who haven’t seen it yet.

“Homer³” easily could be considered the best segment for some; however, there is one better.

1) “The Shinning, “Time and Punishment, and Nightmare Cafeteria” from Treehouse of Horror V

It may seem like cheating to use all three segments from the season six special as the number one pick but, if I were to split them up, half the Top 5 list would be segments from this one episode. Besides, each one of these segments are so hilarious and tense-filled and, unlike most of the Halloween specials, they’re loosely connected to each other which makes it difficult enough to pick just one.

This special starts off with “The Shinning,” a brilliant parody of Stanley Kubrick’s The Shining, that’s equal amount tribute and satire to the iconic horror film and begins the special with a bang. The next is “Time and Punishment” which finds Homer traveling back to the past in an effort to fix the future only to mess things up even worse. It’s probably the best adaptation of the short story, A Sound of Thunder by Ray Bradbury. The opening to “Time and Punishment” features probably one of the funniest scenes in The Simpsons’ history. And to round things out, the final segment, “Nightmare Cafeteria” finds Bart and Lisa having to defend themselves after discovering the teachers at their school are killing kids to serve as lunch. This one is darkly hilarious, genuinely suspenseful, and ends on a note that’ll leave you in stitches as well as reeling in disgust.

Each of these segments are so good, I could write an entire essay about how the writers’ pull off comedy genius while never sacrificing the tension and horror that comes with the subject matter of their plots. If you were to watch only one Halloween special this season, I highly urge you to make it this Treehouse of Horror V. Every segment hits the ground running and never lets up. 

While we could debate endlessly about the show’s quality or which season was the last good one, I think we can all agree that the annual Treehouse of Horror special is always something to look forward to. These may be my favorites but with the show seemingly never going to end, there’s always a possibility that a future one could end up being a classic. Even when a segment misses the mark, it always has something creative about its plot or at least one memorable joke. 

Have a fun socially distant Halloween and be sure to check these picks out if you can! If there’s one you think should have made the list or have a list of favorites of your own be sure to comment. Happy Halloween.

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