Before he was a late night television host, Conan O'Brien wrote several episodes of the classic animated show, including a few of its best.

In the early days of The Simpsons late-night talk show host Conan O’Brien was one of the show's writers. O’Brien was a writer on Saturday Night Live until 1991, when he wrote a television pilot for former Batman, Adam West; NBC passed on the show, leaving O’Brien unemployed until he was brought in to The Simpsons' writers room later that year. During O'Brien's two years with The Simpsons, he created some of the show's best episodes before succeeding David Letterman and hosting The Late Show.

O'Brien's three writing credits on The Simpsons, in addition to some material in the Halloween special and an unproduced episode, feature the combination of his signature zany style and the age-old Simpsons formula. O'Brien also proves his versatility as a writer as each one of the three episodes focuses on a different character.

Though his time on the writing staff was relatively short, O'Brien was nevertheless responsible for some standout moments, and his influence on The Simpsons remains. He created the character Captain Horatio McCallister for his first episode, and his nickname ("Jub-Jub") for Marge's sister's, Patty Bouvier, pet iguana remained part of the show's mythos. These are the Simpsons episodes written by Conan O’Brien.

“New Kid on the Block”

Season 4, episode 8, "New Kid on the Block" is one of The Simpsons' best, and O'Brien's script centers on Bart’s crush on new neighbor, Laura Powers. When Homer and Marge go out on a dinner date, Bart convinces them to let Laura babysit. Despite eating and dancing with Laura, Bart learns that she’s dating one of Springfield’s bullies, Jimbo, and Bart splits them up by making one of his classic prank calls to Moe’s, in which he pretends to be the cigarette-smoking skater.

Homer and Marge’s date provides the introduction to Captain Horatio McCallister, who pitches a restaurant's all-you-can-eat buffet. But things go awry when Homer takes the promotion literally and tries to consume everything on the menu. Homer sues the restaurant, and they eventually settle: the restaurant will allow Homer to eat everything he can if he’ll do it in front of the other patrons for cheap entertainment.

“Marge vs. the Monorail”

Season 4, episode 12, "Marge vs. the Monorail" is Conan O'Brien's favorite of the episodes he penned. After Mr. Burns is busted by the EPA for dumping toxic waste in the playground, Springfield receives a $3 million windfall that they must decide how to spend. However, while Marge wants to put the money into fixing up the town's roads, a con artist named Lyle Lanley, who sings his pitch to the town reminiscent of "Ya Got Trouble" from The Music Man,  suggests hiring him to build a monorail. Lanley wins over Springfield, but Marge uncovers his real motivation: he plans to take the town’s money and flee, allowing the unsafe monorail to destroy Springfield. Undermining Marge, Homer becomes the monorail's conductor, and when the monorail malfunctions on his first day at the job Homer uses an improvised anchor to stop the train. The episode includes a cameo by Leonard Nimoy as one of the monorail's riders and another classic film reference: the man who suggests using an anchor to stop the train looks like Dr. Strangelove.

“Homer Goes to College”

When Homer fails an employee evaluation, Mr. Burns sends him to college. At Springfield University, he befriends a group of nerdy students. He hopes to give them a real college experience, but instead gets them expelled when their plan to steal a rival mascot, Sir Oinks-A-Lot, backfires. Homer’s confession to his involvement - after another failed prank - convinces the dean to accept the nerds back into school. After cramming for and failing his exam, Homer finds the determination to achieve his diploma.

Wraparounds and Unproduced Episode

O’Brien also contributed to the episode “Treehouse of Horror IV,” writing the interstitial parts of the anthology, which included a riff on classic horror series, Rod Serling’s Night Gallery. He wrote one unproduced episode of The Simpsons, as well, which was meant to be a sequel to season 3’s “Stark Raving Dad.” Rather than center on Michael Jackson, O'Brien's unproduced episode would feature Prince.

Conan O’Brien and The Simpsons both feature unconventional, often satirical style, and when the two merged briefly in the early 1990’s, the long-running show produced some of its best work.

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