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“The Simpsons” is one of America’s finest institutions — and nowadays, one of its most reliable. Even after 36 seasons, the longest-running primetime television series continues to produce timeless half-hour episodes (and the occasional hour-long special) that show why it deserves to still be around after so long.
Of course, there is always the “this show used to be better in the ’90s” crowd that can’t dare to imagine newer episodes being anything but garbage. Still, they have a point. The earlier seasons of “The Simpsons” were not just meticulously written and impeccably timed, but they have great animation and phenomenal character writing. It’s why, despite there still being one modern episode, our list of the best “Simpsons” episodes ever is mostly comprised of episodes from seasons 4 to 6.
Among the best episodes, one common element that pops up a lot in that list (at least in the episode credits) is the name Conan O’Brien, America’s other most reliable institution. The comedian, host, actor, and writer hosted one of the most fun Oscar ceremonies in recent memory, and throughout many decades he has been a part of some incredibly well-made comedic projects, from his days writing for “Saturday Night Live” to his recent travel show “Conan O’Brien Must Go.”
Few things have had as big an impact on pop culture as “The Simpsons,” so Conan’s work on the show ranks rather high in terms of his legacy. Besides, these are all quite good episodes (and some all-time greats). Whether you’re at the stage in your “Simpsons” journey that you’re starting to specifically rewatch episodes based on writing or directing credits, or you’re on a Conan-high post-Oscars and want to revisit some of his best work, we’re ranking each episode of “The Simpsons” written by Conan O’Brien. Sadly, there’s one episode he’ll never get to make: a sequel to “Stark Raving Dad” that Conan did rewrites for and supposedly would be centered around Prince. But let’s dig into the episodes that we were fortunate enough to get from the comedian.
4. Treehouse of Horror IV (Season 5, Episode 5)
There is plenty to love about this episode. The segments are great, with “Homer vs The Devil” being the best one in all of “Treehouse of Horror,” and the references are hilarious and creative. Still, this episode ranks lowest simply because Conan O’Brien wasn’t that involved this time around. With the comedian already working on “Late Night on NBC,” O’Brien only wrote the wraparound segments in which Bart walks around a gallery of spooky paintings and introduces each new segment.
The wraparounds are funny, especially the first one where Marge scolds Bart for not warning people about the gruesome and gory nature of the stories they are about to watch. The visuals of the spooky paintings give the episode a unique look of endless imagination, and Bart as a serious Rod Serling-style host is quite fun to watch. Still, the best parts of the episode don’t really involve O’Brien, so this goes at the bottom of the list. Onto better things…
3. New Kid on the Block (Season 4, Episode 8)
Most of early “The Simpsons” treated Bart as a prankster, an often annoying kid that nevertheless stole America’s heart with his excess of attitude and one-liners. Later seasons began to reduce Bart to a spawn of Satan. Still, some of the best episodes of the show treat Bart as a flawed, vulnerable, eternally 10-year-old boy (at least until the eventual series finale) still learning about himself and the world. One such episode is “New Kid on the Block,” an episode that showcases both the rascal aspect of Bart and also his emotional side as writer Conan O’Brien plays with the audience’s heart in a story about Bart having a crush on his new funny bad girl next door, Laura.
Bart completely changes his attitude and behavior (temporarily and not very genuinely, of course) and shows some great emotional vulnerability when interacting with Laura. There’s even a great dance sequence where Bart and Laura turn into Fred Astaire and Ginger Rogers. Then, O’Brien pulls the rug from under the audience and rips out Bart’s little heart when Laura reveals she’s actually dating local bully Jimbo Jones. It’s a great episode that reminds audiences that Bart is still just a kid with a big heart.
Meanwhile, the funniest part of the episode involves Homer in classic “Simpsons” shenanigans that you can apply and quote in everyday situations. This time, Homer goes to an all-you-can-eat seafood joint and sues the restaurant for being kicked out while still hungry (after he devoured every single item in the restaurant). It is absurd, ridiculous, and completely hilarious.
2. Homer Goes to College (Season 5, Episode 3)
Like Bart, Homer has mostly been reduced to a single trait over the years. The man who was once a relatable middle-class father of three with flaws but a well-meaning heart eventually became just the dumbest guy around with little in terms of redeeming qualities. This makes episodes like “Homer Goes to College” all the more special, because they understand the fine balance between making Homer dumb but relatable rather than making him a completely useless fool.
When it becomes clear Homer is not qualified to do his nuclear safety inspecting job, he is forced to go to college to study nuclear physics. The episode sees Homer at his most childish and immature, as he spends most of the episode acting like John Belushi’s character in “Animal House,” shouting “Nerd!” at the first person he sees walking to campus, making pranks and disrespecting everyone.
And yet, even if Homer is quite literally the butt of many jokes (including being literally bit in the butt by a bee), he also has an emotional arc this episode as he genuinely comes to care about the nerds that are tutoring him, as well as the importance of education. Watching Homer go from believing his lived-in experience makes him better than younger academics to having his soul crushed at the first lecture is deeply relatable and heartfelt.
This is the last full episode Conan wrote, and he went out on a big high. Outside of the writing, this episode provides some peak Homer poses and expressions. From his smug face as he tells the class he’s a nuclear physics expert, to his changing “I am so smart” as the wall behind him burns down, there’s a lot of all-time hilarious “Simpsons” moments here.
1. Marge vs. the Monorail (Season 4, Episode 12)
This is it. This is the single best episode of “The Simpsons” ever, the episode Conan O’Brien himself has said will be the thing people remember him for the most — and with good reason. Originating from O’Brien’s love of “The Music Man,” the episode is part of a larger shift in “The Simpsons” going from a relatively grounded and simple satire of American life to a surreal world that takes full advantage of the medium of animation. Rules don’t apply here. and everything goes as long as its funny. A fantasy sequence where Skinner is cut in half by giant mechanical ants? You got it. Escalator to nowhere? Why not. Leonard Nimoy delivering a trippy speech? Sure.
This episode has it all, packing too many jokes and gags in a short runtime that’s impossible to cover them all here. What starts as a straight story of a con man (Phil Hartman delivering a pitch-perfect performance) who convinces the notoriously dumb people of Springfield into investing a fortune into an unnecessary monorail descends into chaos, first in the form of a phenomenal song, then into a “Speed” scenario and a cascade of great jokes. There’s the “Batman’s a scientist” bit, Homer becoming fond of a family of possums at the conductor’s car (“I call the big one Bitey”), and much more.
And yet, once again, Conan knows how to balance jokes with heart. Even if Homer is extremely dumb in this episode, there is something sincere and heartfelt about how happy Homer is about Bart being proud of his new job as a monorail conductor. That is the heart of “The Simpsons” and why it’s lasted so long. Under all the jokes, the surreal moments, the increasingly cartoonish reality, there’s a show about a family just trying their best.
