The Simpsonsis one ofthe greatest animated sitcoms of all time, and it’s been around for so incredibly long now that the list of people who’ve written for the show is quite extensive. Some stayed on for many years, while others stayed on for only a short while. An extreme example would be the cartoon’s very first episode, “Simpsons Roasting on an Open Fire.” It was written byMimi Pond, and that would unfortunately be her only writing credit on the show (which we can apparently blame co-creatorSam Simonfor). Then there’s someone like talk-show legendConan O’Brien,whowrote forThe Simpsonsfor about two seasons. Specifically, the fourth and fifth seasons, which would place him on the staff in around 1992 and 1993. While working on season five, he was given the call to hostThe Late Show—and the rest is history.
Although he wasn’t on the writing team for very long, he nevertheless made an indelible mark on the show.The Simpsonshad a very democratic and collaborative writing process, and Conan has spoken about all the bits he would do to entertain his peers while they struggled to write in a surprisingly crummy writers' room. In terms of actual writing (or co-writing) credits, Conan has only four: the famous “Homer Goes to College,” the very famous “Marge vs. the Monorail,” the also-very-famous “Treehouse of Horror IV,” and the underappreciated “New Kid on the Block.“Below we rank these installments based on not just how good they are, but also on how much Conan participated in the writing process (a nuance that only applies to “Treehouse of Horror IV”).
The Simpsons
4"Treehouse of Horror IV”
Season 5, Episode 5
The Simpsons' fourth Halloween special undoubtedly has a few ofthe greatest Treehouse of Horror segmentsin the series' history, and Conan is credited as one of several writers here. This episode features the segment in which Mr. Burns (Harry Shearer) is a vampire who invites the Simpson family to his home, and it also boasts the one where Flanders (Shearer) plays the devil and takes Homer (Dan Castellaneta) to court. “Terror at 5 1/2 Feet” is another legendary one, but Conan actually wasn’t much involved with them. Since he was already set to become a late-night host, he apparently only had the time to write the in-between parts that introduce each segment. That’s still pretty cool, though, since this is the Treehouse of Horror in which Bart (Nancy Cartwright) takes us on an art gallery tour alaRod Serling’sNight Gallery.
Bart walks past parodies of works by legendary painters, including Vincent van Gogh, Salvador Dalí, and Edvard Munch. It’s charming when Marge (Julie Kavner) interrupts Bart’s introduction to let everyone know they may want to listen toOrson Welles' iconicWar of the Worldsbroadcast on NPR instead. She also hands Maggie to Bart, which humorously undercuts the macabre tone he’s going for while keeping a very Halloween-ish aesthetic. It’s also great when Bart says they had a story for the painting about dogs playing poker but couldn’t show it because it was too intense. Overall, Conan makes sure that the transitions from segment to segment are smooth enough to help make this arguably one ofthe bestSimpsonsepisodes of all time.
3"Homer Goes to College”
Season 5, Episode 3
“Homer Goes to College” is considered by some to be one ofthe funniest inThe Simpsons’canon. We all know that Homer shouldn’t have his job; he understands nothing about nuclear waste, and he never will. Rather than hire someone who knows what they’re doing, however, Mr. Burns would rather send this moron to college instead—an interesting move for someone who thinks so little of Homer that he tells him to keep watch on a bee during an essential nuclear inspection. Sure enough, the education experiment goes just about as well as you’d expect. Much worse, actually. Homer thinks that college is all about pulling pranks and goofing around, so he does some things that anyone other than the nicest dean in the world would crucify him for.
Luckily for Homer (and for us), Conan wrote the dean to be the coolest guy on campus. The man plays a mean bass, and he even knows what a pig fainting sounds like. Homer is a bit more obnoxious than funny here, and it’s a bit out of character for Marge to get so quickly annoyed by the “geeks” that Homer somehow befriends. But that’s okay; the rest of the episode is packed with enough jokes to keep the laughs coming. Especially good moments include missing cinderblocks, a melting van, Grandpa’s inability to leave the car, and one of the funniest questions ever uttered on the show: “Prank?”
2"New Kid on the Block"
Season 4, Episode 8
Bart is always up to something, but he intriguingly develops a crush in “New Kid on the Block.” We get to see the softer side of him, as his older babysitter Laura (voiced bySara Gilbert) is out of his age range and obviously doesn’t consider him a romantic prospect. Poor Bart must experience more than just unrequited love, though; he also finds out that Laura is going out with Jimbo, who’s one of the town’s bullies and amongthe most evil characters Springfield. That doesn’t sit well with him at all, and he goes to some pretty extreme lengths to show Laura that her new beau isn’t worthy of her. The episode ends with a nuanced spin on the recurring prank phone call gag, as well as just about as happy an ending as you could ask for.
Laura is one ofthe most relatable characters in the entire series, and so is her mother. Divorced, Ruth Powers (voiced byPamela Reed) asks Homer if he could set her up with any of his friends—but he’s the last person in the world you should ask for that. This episode may not be as famous as “Homer Goes to College,” but it’s very funny and has a lot more heart. It also introduces Ruth and Laura, who should have been used in many more episodes to come. Ruth is especially one of Conan’s greatest impacts on the show, as she would at least be used to terrific effect in one ofthe greatest episodes of all time: season five’s “Marge on the Lam.”
1"Marge vs. The Monorail"
Season 4, Episode 12
Season four’s “Marge vs. the Monorail” ranks amongMarge Simpson’s greatest episodes. Mr. Burns has been dumping nuclear waste bins into the local trees, a blatant and obvious offense that the Environmental Protection Agency catches wind of. They force him to pay a large sum to the Springfield government, and the citizens fail to use it in a productive way. Marge wanted to use the money to fix Main Street, which is in a comically atrocious condition, but this conman (voiced by the greatPhil Hartman) convinces everyone through the deceptive power of music that paying him to construct a monorail is somehow the superior option.
It turns out that the monorail is more than just unnecessary; it’s very poorly constructed. The break doesn’t work, and there’s a family of possums living inside. And who’s in charge of manning this deathtrap? None other than Homer Simpson, a hilariously arbitrary choice that may be the conman’s biggest blunder. It’s not hard to see why so many fans get a kick out of this one; it’s very much a spectacle, what with the monorail going haywire in a way that puts lots of people’s lives in danger. Marge also investigates the monorail salesman’s history outside of Springfield, which appeals to people who like a little bit of mystery in theirSimpsons. With his wife and son’s help, Homer has to dramatically save the day. Along with guest starLeonard Nimoy’s classic lines, this goes down as one ofseason four’s strongest entriesand arguably Conan O’Brien’s most significant contribution toThe Simpsons.
