When people say that The Simpsons hasn't been funny in years, I always point them to this segment from "Treehouse of Horror XIX." It's an extended spoof of It's the Great Pumpkin, Charlie Brown, but in this case the Pumpkin actually shows up and begins eating people in town as revenge for all the suffering that pumpkins experience every year. The parody could not be more spot on.
"Citizen Kang" was part of the "Treehouse of Horror VII" and was inspired by that year's upcoming presidential election between Bill Clinton and Bob Dole. Though this makes the episode dated, its political satire is still perfect, with its spearing of the two party system and Manchurian Candidate-style plot.
3. Attack of the 50 Foot Eyesores
"Attack of the 50 Foot Eyesores" absolutely nails the tone of '50s monster movies and is hilarious because of it. Watching Chief Wiggum shoot the captain of the high school basketball team never gets old and neither does watching the Lard Lad punt a dog over the horizon.
Based off the classic "Living Doll" episode of the Twilight Zone, featuring a killer "Talky Tina" toy, "Clown Without Pity" takes the already creepy Krusty and turns up his anger to 11. The episode makes the cut on the basis of the "frogurt" scene alone, but it's chock full of jokes that will having you laughing nonstop.
A Nightmare on Elm Street-spoof, "Nightmare on Evergreen Terrace" sees Groundskeeper Willie stepping into the role of Freddy Krueger and terrorizing the kids of Springfield. This is a great episode that just begs for you to curl up around the fire and watch while you stay inside and avoid that lousy Smarch weather. Just try not to fall asleep.
Animating The Simpsons in the third dimension is something that could've come off as completely gimmicky, but it doesn't thanks to the geekiness of the staff. In Homer3, the physics-bending world that Homer accidentally falls into is full of ridiculously nerdy science jokes, animation jokes and pop culture references that still have people like me geeking out 20 years later.
Way before Rick and Morty, Homer Simpson was jumping between time and space and wrecking stuff thanks to his inability to fix a simple toaster. Every single parallel dimension is hilarious, but Homer killing the dinosaurs with a sneeze is one of the greatest gags ever put on film.
This Faustian tale is great, thanks to Homer's penchant for sloth, greed, envy, lust and gluttony, among other deadly sins, but what really makes it stand out is that Ned Flanders is the devil. It does not get better than that, or the "Ironic Punishment Division" of hell, which looks like the most hilarious place to work if you're a demon.
When ranking the best Simpson Halloween segments, every list invariably ends with "The Shinning," which is quite possibly the greatest parody of anything on any show ever, in the history of everything. It's pitch perfect and a loving tribute to The Shining, in every conceivable way. Homer Simpson speaks for every American when he refers to television as his "teacher, mother and secret lover." We'll close out with another quote which could be aptly described as the Sarcasm Society motto, "Go crazy? Don't mind if we do!"