Summary

• Conan O'Brien's writing credits on The Simpsons showcase his zany style and versatility with different characters, creating standout moments and leaving a lasting influence on the show.
• The episodes written by O'Brien, such as "New Kid on the Block" and "Marge vs. the Monorail," combine heartwarming storylines with outlandish humor, showcasing his comedic brilliance.
• O'Brien's final complete episode, "Homer Goes to College," highlights his talent for giving well-established characters like Mr. Burns some of their best moments, while also portraying Homer at his most immature in a hilarious way.

Though he found big success in front of the camera, several of The Simpsons episodes written by Conan O’Brien made for some of the show's classic moments. 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 into 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 as well as versatility with his focus on different characters. 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 funny side character Captain Horatio McCallister and his nickname ("Jub-Jub") for Patty Bouvier's pet iguana remained part of the show's mythos. Looking back on The Simpsons episodes written by Conan, it is a reminder of the brilliance of the series in its golden years.

"New Kid On The Block"

Season 4, Episode 8

The first Simpsons episode written by Conan O'Brien was season 4's "New Kid on the Block" which centers on Bart’s crush on his new neighbor, Laura Powers. When Homer and Marge go out on a dinner date, Bart convinces them to let Laura babysit. Despite feeling a connection, Bart learns that she’s dating one of Springfield’s bullies, Jimbo. Meanwhile, Homer and Marge’s date takes them to Captain Horatio McCallister's all-you-can-eat buffet. However, when Homer takes the promotion literally, it leads to a lawsuit against the restaurant for false advertising which sees the return of Phil Hartman's incompetent lawyer Lionel Hutz.

The episode is a surprising one from O'Brien as the storyline with Bart's early dealings with love is genuinely charming and paints the usually rebellious and unserious Bart in a more vulnerable way. The scene of him learning of Laura's relationship with Jimbo and imagining literally having his heart ripped out is especially memorable. However, the Homer and Marge subplot is the kind of outlandish humor O'Brien is best known for with the unexpected courtroom aspect matching his style. Marge's recounting of her date with Homer ending with him fishing to satisfy his seafood cravings embraces O'Brien's absurdist style perfectly.

"Marge Vs. The Monorail"

Season 4, Episode 12

"Marge vs. the Monorail" is the most famous of The Simpsons episodes written by Conan O'Brien and is one of the best Simpsons episodes of all time. 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. A con artist named Lyle Lanley convinces them to hire him to build a monorail only for Marge to discover his plans to take the town’s money and flee, allowing the unsafe monorail to destroy Springfield. Undermining Marge, Homer becomes the monorail's conductor.

The highlight of the episode is the catchy musical number inspired by The Music Man which is a clear sign of O'Brien's work on the episode. In fact, O'Brien did his own take on the same tune from the musical when he hosted in Emmy Awards in 2006. There are several other great O'Brien gags throughout the episode, including the Leonardo Nimoy cameo, Mr. Burns' over-the-top villainy, and the hilarious ending which reveals Springfield's other misguided purchases, like the "elevator to nowhere." Aside from the individual gags, the episode is an exciting and inventive storyline that mixes character work with outrageous situations, often pointed at as a peak moment for the series.

Where To Watch The Simpsons

"Homer Goes To College"

Season 5, Episode 3

The final complete Simpsons episode written by Conan O'Brien was the high-concept season 5 entry, "Homer Goes to College." When Homer fails an employee evaluation, Mr. Burns sends him to Springfield University where 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.

The episode once again sees O'Brien's talents for giving the well-established characters on the show some of their best moments, like Mr. Burns attempting to recreate Robert De Niro's baseball bat scene from The Untouchables only to be too weak to lift the bat. However, the real fun is seeing O'Brien play with Homer at his most immature. Seeing him trying to live the wild college life of movies like Animal House, only to be met with studious peers and a compassionate dean, makes him look all the more foolish. O'Brien got the job hosting Late Night while he was writing the episode and had to break his contract with The Simpsons to leave.

O'Brien guest-starred on The Simpsons in the season 5 episode "Bart Gets Famous" as himself, host of Late Night

Additional Writing For "Treehouse Of Horror" IV And Unproduced Episode

Season 5, Episode 5/Unaired

Aside from the episodes in which he received sole writing credit, O’Brien also contributed to the fourth installment of The Simpsons' “Treehouse of Horror” special. The anthology episode is a riff on classic horror series, Rod Serling’s Night Gallery with O'Brien writing the wraparound moments between the three stories which include Homer selling his sole for a donut, the gremlin on the side of a school bus, and Mr. Burns as a vampire.

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. Sadly, the story was never revisited and is rendered pointless following Prince's death in 2016. As a result, fans were only treated to three full episodes written by Conan O’Brien but each of them made an impact on the series while highlighting O'Brien's comedic brilliance. O'Brien and The Simpsons both feature unconventional, often satirical style, and seeing those two voices merge briefly in the 1990s was a thrill and provides some of the best episodes to revisit from the long-running series.

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  The Simpsons

  Cast:

  Tress MacNeille, Julie Kavner, Harry Shearer, Pamela Hayden, Nancy Cartwright, Hank Azaria, Dan Castellaneta, Yeardley Smith

  Genres:

  Animation, Comedy

  Seasons:

  35

  Story By:

  Matt Groening and James L. Brooks

  Writers:

  Matt Groening, James L. Brooks, Sam Simon

  Franchise(s):

  The Simpsons

  Directors:

  David Silverman, Jim Reardon, Mark Kirkland

  Showrunner:

  Al Jean

  Release Date:

  1989-12-17

  Network:

  FOX