32 Years Later, ‘The Simpsons’ Officially Wrote This TV Twist Into Reality

If there's one thing The Simpsons is known for, other than being one of the longest-running animated series in history, it's the show predicting events before they happen. Whether it's Disney's acquisition of 20th Century Fox or the outcome of multiple different Super Bowls, The Simpsons' accuracy has led many to wonder if the show's writers are from the future. Considering that co-creator Matt Groening also helped develop Futurama, this might not be too off base. And with former writer Conan O'Brien set to host the Oscars on Sunday, March 15, that reputation feels especially fitting. One episode, in particular, now looks even more uncanny in hindsight.


This ‘Simpsons’ Episode Features Conan O’Brien as a Talk Show Host

O'Brien guest-starred in the Season 5 episode of The Simpsons, "Bart Gets Famous." When Bart (Nancy Cartwright) sneaks onto a TV set, he winds up becoming an assistant for his idol, Krusty the Clown (Dan Castellaneta). Eventually, Bart gets to be on The Krusty Show, but ends up knocking over a bunch of props. When confronted about this, he says, "I didn't do it," which catapults him into fame overnight. This eventually leads to an appearance on a talk show hosted by none other than Conan O'Brien, who asks him to say his line, which Bart is getting sick of. In true Simpsons fashion, this leads to a hilarious moment where Bart tries to dance along with O'Brien — only for O'Brien to admonish him: "Sit perfectly still. Only I may dance."


Conan O’Brien Was Auditioning for a Talk Show Host Job During ‘The Simpsons’

Though O'Brien's appearance on The Simpsons was meant to be satirical, he was actually auditioning for the role of a talk show host at the time. David Letterman had just left the Late Night show on NBC, and the network was scrambling to find a host. The Simpsons writers decided to insert O'Brien into "Bart Gets Famous" as a joke, not knowing if he'd get the job or not. “Even though the Conan O’Brien show did not exist yet, we decided to put (Bart) on the Conan O’Brien show and make Conan a character,” former Simpsons showrunner David Mirkin said on the commentary for "Bart Gets Famous." “But we were writing this before the information came in, so we actually wrote it in secret, not telling Conan that we had put him in the show, just in case. Although we were confident.”

That confidence paid off, as O'Brien would go on to host the late show until 2009. He'd actually recorded lines for "Bart Gets Famous" after the premiere of Late Night with Conan O'Brien, but didn't feel like he would last very long. "The (Late Night) show was on the air when I did the record, and I remember at the time thinking, ‘This is very optimistic of The Simpsons'. It was just after Chevy Chase had been canceled, and people thought I would last about eight weeks. I thought there’s a good chance I won’t be on the air when this airs, and it’ll just be this sad, ironic thing," O'Brien recollected.


Conan O’Brien Has a Long History With ‘The Simpsons’

Before his Late Night gig, Conan O'Brien wrote a handful of episodes for The Simpsons. His first credited episode was Season 4's "New Kid On The Block," which happened to be another Bart-centric episode. Bart grows a massive crush on his new neighbor, Laura (Sara Gilbert), only to find out she's dating one of his bullies, Jimbo Jones (Pamela Hayden). He'd also write the Season 5 episode "Homer Goes To College" and parts of the "Treehouse of Horror IV" special, which featured Bart in a parody of Rod Serling's Night Gallery. These episodes feature O'Brien's penchant for well-timed humor; Homer shouting "NERD!" at passersby in "Homer Goes To College" or going to court over an all-you-can-eat buffet in "New Kid On The Block" remain great Simpsons moments.

O'Brien's biggest contribution to The Simpsons is the Season 4 episode "Marge vs. the Monorail." "Marge vs. the Monorail" is often considered to be one of the episodes that make up the "Golden Age" of The Simpsons, due to several elements that O'Brien deploys throughout the episode. There's a strong focus on Marge (Julie Kavner), who has objections to the monorail project being launched in Springfield; in fact, this is one of the strongest episodes with the Simpsons matriarch at its center. There's the iconic "Monorail Song," where Lyle Lanley (Phil Hartman) manages to sway all of Springfield into supporting the monorail. And who could forget Leonard Nimoy's incredible cameo? In fact, it was this episode that clued the other Simpsons writers into O'Brien's gift for comedy. "Conan sold three script ideas at that meeting – his first meeting – and I don’t think anyone had ever done that, before or since," former Simpsons showrunner Mike Reiss said in an oral history of "Marge vs. the Monorail."

O'Brien would eventually return to the world of The Simpsons in a roundabout way during his exit interview for Conan, the talk show he hosted on TBS. That interview was animated and featured none other than Homer Simpson as the interviewer. In true Simpsons/O'Brien fashion, it's full of witty barbs as well as references to Conan's time writing for The Simpsons. But it also leads to a surprisingly emotional moment where Homer tells Conan he means the world to him — even if it's dinged slightly by him calling Conan "Conrad." Since The Simpsons was a large part of O'Brien finding his comedic voice, and eventually led to his career hosting late-night shows on NBC and TBS, it made sense that he'd return to Springfield one last time.