43. Terror of Tiny Toon

• Treehouse of Horror: IX
• Year: 1998
• Synopsis: Bart and Lisa are sucked into an Itchy and Scratchy cartoon
• Rating: ★★★☆☆
• Best Gag: Lisa: “Characters in a cartoon. How humiliating.”

This segment is fine –not great, but not bad– but it does feel like a shift. It’s the first one with an egregious guest star appearance, and maybe the first one where that particular gag is the crux of the bit. Sure, there’s some meta humour in it too, but this feels like the first big step in the wrong direction.

42. Wiz Kids

• Treehouse of Horror: XII
• Year: 2001
• Synopsis: Bart and Lisa attend a school of witchcraft and wizardry
• Rating: ★★★☆☆
• Best Gag: Slithers, as he slowly eats lord Monty-mort: “In death, we shall be together always!”

A solid parody of Harry Potter at the height of Potter-mania. Bart’s toad-prince is simultaneously the best and worst thing about the story, being both instantly iconic and entirely reliant on the shock and gross-out value.

41. Untitled Robot Parody

• Treehouse of Horror:
• Year: 2008
• Synopsis: It’s transformers.
• Rating: ★★★☆☆
• Best Gag: One of the transformers is called “Bestimus Mucho” and I find this unreasonably hilarious

A Malibu Stacy convertible given as a gift turns out to be a transformer and starts turning all the other tech in town into transformers. It’s kind of like Michael Bay’s Transformers but intentionally funny.

Also, this episode opens with a super dark gag in which Grandpa Simpson wants to go outside and play with his new oxygen supply and then dies in the background.

40. Don’t Have A Cow, Mankind

• Treehouse of Horror: XX
• Year: 2009
• Synopsis: Krusty Burger makes a hamburger patty out of cows that have eaten other cows and they turn people into zombies.
• Rating: ★★★☆☆
• Best Gag: Apu, surviving the zombie apocalypse: “As a vegetarian, I did not consume any tainted meat.  As a convenience store owner, I am armed to the teeth.“

A riff on 28 Days Later and I Am Legend and a good one at that. Lots of solid gags, and I love the cause of the zombie apocalypse being Krusty Burgers “Burger²“, which is made from cows that have been fed other cows. Honestly, that sounds like something a soulless fast-food chain have probably already tried.

39. Frinkenstein

• Treehouse of Horror: XIV
• Year: 2003
• Synopsis: Professor Frink re-animates his dead father, played by Jerry Lewis, who becomes an organ harvesting monster.
• Rating: ★★★☆☆
• Best Gag: Frink winning the Nobel Prize for inventing a hammer with a screwdriver on the other side

Another one that isn’t bad but relies too much on the fact that they got Jerry Lewis to be the voice of Frink’s father. Bonus points, too, for She Blinded Me With Science playing when Frink walks on stage to accept his Nobel Prize.

38. Mmm… Homer

• Treehouse of Horror: XXVIII
• Year: 2017
• Synopsis: Homer develops a taste for himself.
• Rating: ★★★☆☆
• Best Gag: Homer: “I can’t eat my finger, it’s unholy. Also, it’s not done.“

Homer being left to his own devices and then resorting to self-cannibalism when he runs out of food (except a fridge full of vegetables) is just the kind of bonkers I like from this show. The segment never goes off the rails and into weird, unexpected places; it’s just a nice little self-contained thing.

37. Heck House

• Treehouse of Horror: XVIII
• Year: 2007
• Synopsis: Bart, Lisa, Nelson, and Milhouse start playing tricks instead of asking for treats.
• Rating: ★★★☆☆
• Best Gag: Bart: “Trick or treat isn’t just some phrase you chant mindlessly like the lord’s prayer, it’s an oral contract!”

Heck House seems like it’s going to be boring until Flanders is transformed into The Devil and takes everyone to hell, where ironic punishments for the seven deadly sins abound.

Look, I like ironic punishments, ok?

36. Bad Dream House

• Treehouse of Horror: I
• Year: 1990
• Synopsis: In the first-ever segment of the first-ever Treehouse of Horror, The Simpsons move into a haunted house.
• Rating: ★★★☆☆
• Best Gag: Lisa: “It destroyed itself rather than live with us. You can’t help but feel a little slighted”

This is the lowest-ranked of the original three segments, and while there’s nothing wrong with it. Bart chiding the house into bleeding is pretty good, but unlike the other segments in this episode, something is lacking compared to the other two it accompanies.

Do make sure to keep an ear out for the James Earl Jones cameo!

35. Homer’s Nightmare

• Treehouse of Horror: II
• Year: 1991
• Synopsis: Br Burns puts Homer’s brain a robot.
• Rating: ★★★☆☆
• Best Gag: Mr Burns to Smithers: “He is alive, I guess I owe you a coke!”

A fun riff on Frankenstein that might be a classic if it weren’t quite so overstuffed and fast-paced. Casting Mr Burns as a mad scientist is a stroke of genius, and Robot Homer going straight for the doughnuts is, well, of course, he does.

34. Bart’s Nightmare

• Treehouse of Horror: II
• Year: 1991
• Synopsis: Bart can alter reality with his mind and terrorizes his family with said power.
• Rating: ★★★☆☆
• Best Gag: Bart waking up in terror when he realizes Homer loves him.

This is another one that feels like it could have been a classic if it just had a little more going for it. The parody is good, and the visuals are good, but it’s decidedly short on laughs.

33. Desperately Xeeking Xena

• Treehouse of Horror: X
• Year: 1999
• Synopsis: Bart and Lisa are imbued with superpowers, and meet Lucy Lawless
• Rating: ★★★☆☆
• Best Gag: The Collector to Lucy Lawless: “You will be sealed in this mylar bag, forever remaining in … mmmm near mint condition.”

The tenth Halloween Special was an early example of the show going for big guest stars, and this original story delivers a few great gags and more than a few iconic Comic Book Guy lines.

32. E.T., Go Home

• Treehouse of Horror: XVIII
• Year: 2007
• Synopsis: Bart finds a lone Kodos in the butane storage shed.
• Rating: ★★★☆☆
• Best Gag: Kodos: “My friend and I came in peace to find your vulnerabilities… and shore them up with more peace”

It starts all E.T. and then ends with an alien invasion and attack helicopters. The whole section in the middle where they have to escape the military and Kodos kills several soldiers and agents is hilarious, and the revelation that it is good to judge a book by its cover is perfect.

31. In the Belly of the Boss

• Treehouse of Horror: XV
• Year: 2004
• Synopsis: Mr Burns swallows a pill that contains a shrunken Maggie, and the family shrinks down to go after her.
• Rating: ★★★☆☆
• Best Gag: Mr Burns: “While you’re in there grab as much cancer as you can”

Another bit of strong source material to riff on, and it mostly succeeds. Belly of the Boss also has some great Frink lines (“let the commencement beginulate!”) and references (listen carefully, the ship sounds are all Star Trek sounds) but doesn’t quite make the cut for all-time great segments.

30. Into the Homerverse

• Treehouse of Horror: XXXI
• Year: 2020
• Synopsis: Multiple Homers are pulled from various universes to Homers.
• Rating: ★★★☆☆
• Best Gag: “This case is going to be like Homer’s skull, hard to crack and not much inside.“

Into the Homerverse is a pretty spot-on play on Into the Spider-Verse, right down to the kinds of Homers that we meet, all of whom are funny. Marge struggling to feed them all is also a hilarious moment, but as in the film, it’s Noir Homer who ends up stealing the show even if Anime Homer has one of the best gags. Plus, the reveal at the end is gold.

29. Wanted: Dead, Then Alive

• Treehouse of Horror: XXVI
• Year: 2015
• Synopsis: Sideshow Bob finally manages to kill Bart.
• Rating: ★★★☆☆
• Best Gag: Sideshow Bob: “24 years of trying to kill a 10-year-old finally paid off!”

A dog chasing a car wouldn’t actually know what to do if it caught the damned thing, and Sideshow Bob’s life becoming unfulfilling once he accomplished his goal is hilarious. Bob building a re-animation machine to kill Bart over and over is funny every time (plus the montage of gathering the pieces for the machine is great, too).

28. G-G-Ghost D-D-Dad

• Treehouse of Horror: XI
• Year: 2000
• Synopsis: Homer dies but hasn’t done enough good deeds to get into heaven.
• Rating: ★★★☆☆
• Best Gag: Homer: “I thought you people could see everything?” St Peter: “No you’re thinking of Santa Claus”

This one is rated as high as it is based almost entirely on the opening few minutes: Homer’s horoscope lets him know an attractive coworker might compliment him, and he perks up when he thinks it might be Lenny. Then when it also tells him he’s going to die, and he starts waving it around, mocking it for trying to scare him, and then he accidentally cuts his wrist with it.

That and almost everything St Peter says.

27. Moefinger

• Treehouse of Horror: XXVII
• Year: 2016
• Synopsis: Bart is recruited to a secret intelligence agency to avenge the death of his father.
• Rating: ★★★☆☆
• Best Gag: Homer: “I suppose you’re wondering why I cornered the world beer supply.  I’ve created a lava machine that will force the world to surrender to me and I want all the beer to celebrate.”

A mix of Kingsman: The Secret Service and James Bond, Moefinger is right up my alley. There are some fun fight scenes, the send-up of the church fight from Kingsman, in particular, is fun, and Homer has a couple of absolutely killer lines.

Also, as this was the 600th episode of The Simpson’s, they wrote a James Bond-style song for the end credits that is just excellent.

26. The Others

• Treehouse of Horror: XXV
• Year: 2014
• Synopsis: A past incarnation of themselves haunts the Simpson’s.
• Rating: ★★★☆☆
• Best Gag: Homer, as the ghost of past Marge levitates the bed: “I demand you put me down right after the sex!”

It’s easy to forget sometimes how far The Simpson’s have come just from a character design point of view. The voice work by the whole cast recreating the old voices alongside the new is fun, and the big reveal at the end of the infinite incarnations of the characters is also a fun moment to watch.