25. Toy Gory

• Treehouse of Horror: XXXI
• Year: 2020
• Synopsis: Barts Toys are alive, and they want revenge.
• Rating: ★★★☆☆
• Best Gag: Krusty Doll: “Even you hate him gift-that-was-never-unwrapped? Wow, so much anger. I always thought you were just a sweater.”

Imagine the movie Toy Story but make the creepy mean kid from next door the protagonist, and that’s basically what we’re talking about, and the story jumps right to the toys revenge. This whole episode is 3D animated, and it looks amazing, in addition to being fun and funny.

24. Hell Toupée

• Treehouse of Horror: IX
• Year: 1998
• Synopsis: Homer gets a hair transplant from Snake, who possess him.
• Rating: ★★★☆☆
• Best Gag: As Lisa starts to explain that Snakes hair must be possessing Homer, Marge saying “Please Lisa everyone’s already figured that out”

Another solid entry with some genuinely great moments. Snake is pretty much always great and him taking over Homer is pretty fun. Plus, the moment when Chief Wiggum says, “you’ll never harm another person with second-hand smoke!” and then everyone starts coughing due to the smoke from Snake being electrocuted is pretty great.

23. The Thing and I

• Treehouse of Horror: VII
• Year: 1996
• Synopsis: Bart has a twin brother whom Homer and Marge have been keeping in the attic.
• Rating: ★★★☆☆
• Best Gag: Doctor Hibbert describing Hugo as “Too crazy for Boystown, too much boy for Crazytown”

Admit it; you knew the big reveal at the end was coming even the first time you saw this one.

This is a stand out Doctor Hibbert episode, with nearly everything he says being solid gold. The “I bet you have never even seen your own face in a mirror” gag is a classic.

22. Be Nine, Rewind

• Treehouse of Horror: XXXI
• Year: 2020
• Synopsis: Lisa is caught in a time loop on her birthday
• Rating: ★★★☆☆
• Best Gag: Comic Book Guy: “The time loop is simultaneously the most ambitious and laziest of science fiction tropes”

The time loop really is the most ambitious and laziest of all tropes, but it’s one of the best when it’s executed well. This riff on Russian Doll with Lisa and Nelson stuck in the loop together is pitch-perfect, fun, and funny.

Being the highest-rated of this year’s segments, it’s also proof that the Simpson’s is still good when they want to be.

21. Night of the Dolphin

• Treehouse of Horror: XI
• Year: 2000
• Synopsis: Lisa frees a dolphin from captivity who turns out to be the dolphin monarch, which then leads a campaign of revenge against the humans of Springfield.
• Rating: ★★★☆☆
• Best Gag: Chief Wiggum: “Bottlenose bruises, blowhole burns, flipper prints, this looks like the work of rowdy teens! Lou cancel the prom!”

This is one of the more ridiculous segments, and I kind of love it for that. It’s nuts, but it has at least one great death and a lot of great lines along with a super weird premise.

20. The HΩmega Man

• Treehouse of Horror: VII
• Year: 1997
• Synopsis: Homer is the last man on earth.
• Rating: ★★★☆☆
• Best Gag: “This baby can take a six megaton blast. No more, no less.”

This parody of 1970s classic Charlton Heston film The Omega Man is one of the better parodies to date at this point. The scenes of Homer doing whatever he wants after he figures out he can do whatever he wants is pretty great.

19. The Devil and Homer Simpson

• Treehouse of Horror: IV
• Year: 1993
• Synopsis: Homer sells his soul to the devil, Ned Flanders, for a doughnut
• Rating: ★★★☆☆
• Best Gag: Homer, reading a note he has left to himself: “Dear homer I owe you one emergency doughnut.  Bastard, he’s always one step ahead!”

This one being only three stars and rated as low as it is one that I expect some backlash on, but while it has a few good gags (I especially like the “ironic punishment department” in hell), it really didn’t hold up as well as expected for me. Still, “Mmmmmm, forbidden doughnut…” might be one of the most quotable lines in the whole series.

18. Clown Without Pity

• Treehouse of Horror: III
• Year: 1992
• Synopsis: Bart’s new Krusty The Clown doll is evil.
• Rating: ★★★☆☆
• Best Gag: The entire frozen yoghurt exchange

Here’s another from the classic early days that didn’t resonate with me as much as I thought it would, but this episode secures its spot in this ranking and Simpson’s history for Homer’s exchange with the proprietor of the cursed items shop about the Krusty doll being cursed, which is bad, but it comes with frozen yoghurt, which is good. It might be one of the funniest things they ever did.

17. When Hairy Met Slimy

• Treehouse of Horror: XXX
• Year: 2019
• Synopsis: Selma falls in love with Kang, a la The Shape of Water
• Rating: ★★★★☆
• Best Gag: Selma: “My sister says you just wanna eat me, or for a green card, or for a human zoo.”  Kang: “Two of those are ridiculous” 

The Shape of Water is a good movie, and it turns out that if you parody it, then you will end up with a good segment, too. It’s also quite funny, with Homer’s version of stalling being a moment I am sure I’ll be quoting for ages.

16. Tweenlight

• Treehouse of Horror: XXI
• Year: 2010
• Synopsis: Lisa falls in love with a local boy who turns out to be a vampire
• Rating: ★★★★☆
• Best Gag: Homer: “Pretty ironic, a cross being used to kill someone!”

This Twilight parody is funny from start to finish, and Daniel Radcliffe has some great line deliveries as Edmund. Homer eventually putting himself in harm’s way and killing the vampires with his cholesterol is also a pretty funny payoff at the end.

15. Reaper Madness

• Treehouse of Horror: XIV
• Year: 2003
• Synopsis: Homer becomes death.
• Rating: ★★★★☆
• Best Gag: Homer: “Death! Death! We miss you so much! You were a busboy in the restaurant of life. Clearing away the oldies and the sickies and the junkies. And you made NASCAR racing exciting!”

Season 15 is solidly out of what many consider to be the golden age of The Simpsons, but this segment is funny from start to finish, and it starts with a Benny Hill-style scene of death chasing the family throughout the house.

Once Homer becomes death things ramp up, but the resolution and the final lines from God really hammer this one home for me.

14. House of Whacks

• Treehouse of Horror: XII
• Year: 2001
• Synopsis: The Simpson’s buy a cybernetic smart home with Pierce Brosnan for a voice.
• Rating: ★★★★☆
• Best Gag: Brosnan: “Don’t take out my British charm unit! Without that, I’m nothing but a boorish American clod!” “Aaaah thanks a lot, ass wipe!”

One of the better examples of an egregious guest star, with a solid premise and a lot of good laughs, but part of me can’t help but wonder if this one had been a more direct parody of Demon Seed than it is of 2001: A Space Odyssey.

13. Homer³

• Treehouse of Horror: VI
• Year: 1995
• Synopsis: Homer ends up trapped in the hypothetical “third dimension”
• Rating: ★★★★☆
• Best Gag: Homer: “This place looks expensive. I feel like I’m wasting a fortune just standing here. ” <belch>

This might be one of the more memorable segments just because it was the early days of CG animation. Remember, when this episode premiered in October 1995, Toy Story (the first feature-length CG animated film) was still a month away.

The animation holds up well today; you can tell they weren’t going for “real”, and it works. The episode is filled with good laughs, including one of my favourite jokes in the whole episode, which is when Homer is disappeared, and they call Flanders “because he has a ladder,” and in the next scene, Flanders is in the living room standing at the top of his ladder. It’s exactly the kind of nonsense that I love.

12. Dial “Z” for Zombies

• Treehouse of Horror: III
• Year: 1992
• Synopsis: Bart accidentally raises the dead.
• Rating: ★★★★☆
• Best Gag: Homer: “Glad we didn’t turn into zombies! Mmmmm. TV.”

Dial Z for Zombies isn’t a parody of any specific zombie film, but it doesn’t need to be; the tropes were well-worn even in 1992. This segment is filled with so many good minor jokes (such as all the bookshelves in the library’s occult section being #666, or the book title “selling your soul in a buyers market”, plus a lot of classic Homer lines.

11. Nightmare on Evergreen Terrace

• Treehouse of Horror: VI
• Year: 1995
• Synopsis: Groundskeeper Will returns from the dead to take revenge on the children of Springfield
• Rating: ★★★★☆
• Best Gag: Skinner: “Next vote, $2 for doorknob repair.” Everyone in attendance: “Nay.”

Honestly, this one might rank as high as it does because Willie makes some excellent puns as he stalks the children in their dreams, but also for gags like it being the 13th day of the 13th month and the PTA meeting to discuss the misprinted calendars the school had bought.

Plus, all of the nightmares are good. I am particularly fond of Willie as a giant bagpipes spider.