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27. Starship Poopers (October 25, 1998 – “Treehouse of Horror IX”)

So, Maggie’s real dad is Kang—the alien? Wild premise, right? Marge having a “moment” with him? Kinda funny at first. But then it turns into a Jerry Springer parody. Let’s be real—Springer was huge then, but now? It’s like finding an old pair of platform shoes in your closet. You remember why you loved ’em, but they don’t fit quite right. Homer and Kang bickering? That’s the good stuff. But it’s missing that clever, heartfelt twist the best “Treehouse” bits have.

26. The HΩmega Man (October 26, 1997 – “Treehouse of Horror VIII”)

Homer as the last man on Earth? That should be comedy gold. Imagine it—him raiding the grocery store, sitting on the couch with no one to tell him to turn down the TV. And yeah, there are funny bits (him dancing alone to old records? Relatable). But then the mutated Springfield folks show up as bad guys, and it feels… rushed. Like they had a great idea but didn’t have time to cook it all the way. It needed more room to breathe.

25. Fly vs. Fly (October 26, 1997 – “Treehouse of Horror VIII”)

This one’s a straight-up parody of The Fly. Homer buys a transporter, Bart messes with it (because of course he does), and boom—Bart’s tiny head on a fly’s body. That image? Stuck in my brain forever. But the story itself? Kinda one-note. Gross-out fun, which fits “Treehouse” to a T… but it doesn’t stick with you like the bigger, bolder segments.

24. Hell Toupée (October 25, 1998 – “Treehouse of Horror IX”)

Homer gets a hair transplant from Snake—the executed criminal. Cue him getting possessed by Snake’s ghost. First off: Homer with a full head of luscious hair? Chef’s kiss. The murder spree (played for laughs, obviously) is goofy. But compared to the heavy hitters we’re gonna get to? It’s just… light. Like a donut with no sprinkles—still good, but missing something.

23. Easy-Bake Coven (October 26, 1997 – “Treehouse of Horror VIII”)

Set in 1649, Puritan Springfield. Marge gets accused of witchcraft. Smart take on the Salem witch trials—they make fun of how absurd those accusations were (like, “She turned my broom into a mop! Witch!”). The best part? Finding out Marge is a witch. Fun origin story for Halloween… but I’ll be honest, I forget it sometimes when I’m listing my faves.

22. Attack of the 50-Foot Eyesores (October 29, 1995 - “Treehouse of Horror VI.”)

A weird ionic storm hit Springfield. It made the town’s huge advertising mascots come alive. Then those mascots started causing trouble.

Seeing the giant Lard Lad donut boy going wild? That’s a classic “Treehouse of Horror” image.

The way it ends is clever. The townspeople just stop looking at the monsters to beat them. That’s a little comment on society. But the segment itself doesn’t have many moments you’ll remember.

21. King Homer (October 29, 1992 – “Treehouse of Horror III”)

Black-and-white parody of the 1933 King Kong. They nailed the old-movie vibe—details, music, everything. Homer as the giant ape? Perfect. His little moments with Marge? Actually sweet. But here’s the thing: it’s more of a loving tribute than a laugh-out-loud bit. Still good, just not as funny as the rest.

20. Bad Dream House (October 25, 1990 – “Treehouse of Horror”)

The first ever “Treehouse” segment. It set the stage for everything. The Simpsons move into a house built on an Indian burial ground. Walls bleed, objects fly, a voice yells “GET OUT!” It’s the perfect intro to their spooky-silly Halloween style. But compared to the weirder, more ambitious segments later? It’s pretty straightforward. Still, I’ll always have a soft spot for it—my first “Treehouse” memory.

19. If I Only Had a Brain (October 31, 1991 – “Treehouse of Horror II”)

Frankenstein vibes here. Mr. Burns tries to make the perfect employee by putting a human brain into a giant robot. Guess whose brain he picks? Homer’s. So now you’ve got a robot that’s lazy, loves donuts, and can’t do anything right. The visual gags? Great—robot Homer tripping over his own feet, forgetting how to use a stapler. Solid, funny, and plays to exactly why we love Homer.

18. Hungry Are the Damned (October 25, 1990 – “Treehouse of Horror”)

This is how we met Kang and Kodos—those lovable, always-hungry aliens. They abduct the Simpsons and feed ’em fancy meals. Lisa gets suspicious: “Wait, are you fattening us up to eat?” The twist? Their cookbook, How to Cook for Forty Humans, was a misinterpretation. They just wanted to feed them, not feast on them. Classic Simpsons move—taking a horror trope and flipping it. Charming, funny, and gave us two of the show’s best recurring characters. My friend still quotes Kang’s line about “delicious Earth snacks.”dc

17. The Bart Zone (October 31, 1991 – “Treehouse of Horror II”)

This one parodies The Twilight Zone’s “It’s a Good Life.” Bart has godlike powers. He can read minds. He can change reality. Whatever he wants, really. Springfield’s scared to make him mad. The best part? Homer turns into a jack-in-the-box. When I was a kid, that made me laugh so hard I snorted soda out my nose. True story. It shows Bart’s mischief perfectly. Chaotic. Funny. And just a little creepy.

16. The Genesis Tub (October 27, 1996 – “Treehouse of Horror VII”)

Lisa’s science fair project: a tooth and some soda. Accidentally creates a tiny civilization. Those little people evolve super fast—they worship Lisa as a god and think Bart’s the devil (fair). It’s clever, imaginative… and the ending’s surprisingly sad. Lisa loses her tiny world, and you kinda feel for her. Not just a funny bit—has a little heart, too.

15. The Thing and I (October 27, 1996 – “Treehouse of Horror VII”)

Bart finds out he has an evil twin, Hugo, locked in the attic. Evil twin trope? Done a million times. But this one? They twist it—turns out Bart was the evil one all along. Genius. It’s funny, a little spooky, and exactly the kind of “wait, what?!” moment that makes “Treehouse” great. I still bring this up when my sister and I argue about who’s the “good twin.”

14. Nightmare Cafeteria (October 30, 1994 – “Treehouse of Horror V”)

Springfield Elementary has a budget crisis and too many kids. Solution? Principal Skinner and the teachers start eating the students. Dark? Oh yeah. But so funny—they lean into the absurdity. “Sloppy Jimbos” (gross, but hilarious), and that final reveal about the fog that turns people inside out? I still get a little grossed out thinking about it… in a good way.

13. The Terror of Tiny Toon (October 25, 1998 – “Treehouse of Horror IX”)

Bart and Lisa get zapped into their TV—trapped in The Itchy & Scratchy Show. If you grew up watching cartoons, this hits. The parody of cartoon violence? Brilliant. And that live-action bit on Live with Regis and Kathie Lee? So weird, so random… so Simpsons. I remember rewinding that part on my VHS tape (yes, VHS) just to watch it again.

12. The Raven (October 25, 1990 – “Treehouse of Horror”)

They adapted Edgar Allan Poe’s The Raven—and did it right. Homer’s the narrator, Bart’s the raven. The animation’s beautiful, and James Earl Jones’s narration? Chills. It’s not just funny—it’s a love letter to classic literature. I even remember my English teacher showing this in class once. (Thanks, Ms. Smith—you get it.) It’s smart, it’s spooky, and it works for both kids and adults.

11. Bart Simpson’s Dracula (October 28, 1993 – “Treehouse of Horror IV”)

The Simpsons go to Mr. Burns’s castle in Pennsylvania… and he’s a vampire. Parody of Coppola’s Dracula, and they nail every detail. The twist? Marge is the head vampire. And that final scene—parodying A Charlie Brown Christmas? So surreal, so sweet. I still quote Mr. Burns’s “I vant to suck your… lemonade?” line. (Okay, maybe I made that up, but it’s close.)

10. Homer³ (October 29, 1995 – “Treehouse of Horror VI”)

Homer hides from Patty and Selma (relatable) and stumbles into a 3D world. Back in 1995, that CGI was groundbreaking. It looked so cool—like nothing we’d seen on The Simpsons before. The story’s fun, too—Homer wandering this weird, blocky world. And the ending? Him getting transported to the real world? Mind-blowing for a kid. I still think about that 3D Homer sometimes.

9. Time and Punishment (October 30, 1994 – “Treehouse of Horror V”)

Homer turns his toaster into a time machine. Every trip to the past messes up the future. Parody of Ray Bradbury’s “A Sound of Thunder,” but with Simpsons chaos. One future: Ned Flanders is the ruler (scary). Another: it rains donuts (heaven). Each alternate reality is funnier than the last. I could watch Homer bumble through time all day.

8. Clown Without Pity (October 29, 1992 – “Treehouse of Horror III”)

Homer buys Bart a Krusty the Clown doll for his birthday. Turns out, it’s cursed and wants to kill Homer. Parody of Child’s Play, and it’s hilarious. The doll’s little evil quips? Perfect. And the twist? The doll has a switch—“evil” or “good.” Homer just flipped the wrong one. Classic Simpsons—taking a horror trope and making it silly. I refused to get a talking doll for years after this. (No regrets.)

7. Nightmare on Evergreen Terrace (October 29, 1995 – “Treehouse of Horror VI”)

A Nightmare on Elm Street parody. Groundskeeper Willie is Freddy Krueger, terrorizing Springfield’s kids in their dreams. The dream sequences? So clever—like Willie coming out of a chalkboard. And Willie’s one-liners? Perfect. The final fight between Willie and the Simpson kids? Thrilling and funny. I still think Willie’s a little scary in this… but in a good way.

6. Terror at 5½ Feet (October 28, 1993 – “Treehouse of Horror IV”)

Another Twilight Zone parody—“Nightmare at 20,000 Feet.” Bart’s the only one who sees a gremlin taking apart the school bus. The paranoia? So real. You’re yelling at the screen, “Believe him!” And the ending? The gremlin’s real… but Bart still gets sent to a mental institution. Dark, funny, and exactly why I love these segments—they don’t pull punches.

5. Dial “Z” for Zombies (October 29, 1992 – “Treehouse of Horror III”)

Bart tries to bring back the family cat… and accidentally raises the dead. Zombie apocalypse in Springfield! It’s a love letter to classic zombie movies. The best part? Homer going, “I’m a zombie?” like it’s no big deal. And the ending—family safe on the couch, zombies outside? Darkly perfect. I used to pretend my stuffed animals were zombies after watching this. (Sorry, Teddy.)

4. Citizen Kang (October 27, 1996 – “Treehouse of Horror VII”)

Kang and Kodos abduct Bill Clinton and Bob Dole, then impersonate them for the 1996 election. The political satire? Sharp. The lines? Iconic. (“Abortions for some, miniature American flags for others!”) The ending—Americans have to choose between two aliens—so cynical, so funny, and honestly? Still kinda true. This one’s smart, it’s timely (even now), and it’s one of the most quotable segments ever.

3. The Monkey’s Paw (October 31, 1991 – “Treehouse of Horror II”)

The Simpsons get a cursed monkey’s paw that grants four wishes. Every wish backfires. Wish for world peace? Aliens invade (since there’s no war to stop them). Wish for a turkey sandwich? It’s too dry. Classic cautionary tale, but with Simpsons humor. It’s a masterclass in irony—funny, clever, and makes you think twice about wishing for things. I still joke about “dry turkey sandwiches” when someone complains about a bad wish.

2. The Devil and Homer Simpson (October 28, 1993 – “Treehouse of Horror IV”)

Homer sells his soul to the devil… who’s Ned Flanders. For a single donut. Let that sink in. The trial for Homer’s soul? “Jury of the damned” (including Hitler and Richard Nixon—yikes). Him escaping hell by eating the donut (which was part of the deal)? Genius. And the ending—Homer’s head turns into a donut? Iconic. I’ve seen this segment a hundred times, and I still laugh at Ned as the devil. “Hi-diddly-ho, sinner!”

1. The Shinning (October 30, 1994 – “Treehouse of Horror V”)

C’mon. You knew this had to be number one. Parody of Kubrick’s The Shining, and it’s perfect. “No TV and no beer make Homer go crazy” scrawled on the walls? I quoted that so much my mom threatened to hide the remote. Ghostly Moe telling Homer to kill his family? Chilling, but funny. It’s a love letter to the original movie, but it’s also 100% Simpsons. Spooky, silly, and the absolute best of the golden age. I watch this every Halloween—no exceptions.

Okay, so that’s our list. But let’s be real—you’re already disagreeing. And that’s the magic of these old “Treehouse” segments. We all have that one we’d fight for. Maybe you think “Hungry Are the Damned” should be top 5. Maybe you’re mad “The Raven” isn’t higher. Or maybe you’re a weirdo who loves “Starship Poopers” (no judgment).

Either way, let’s hear it. What’s your all-time favorite? Which one did we totally rank too low? Spill in the comments—this conversation’s just getting started.