Conan O'Brien Was Warned Not To Pitch His Most Famous Simpsons Episode

33 years after it first aired, "Marge Vs. the Monorail" remains one of the best episodes of "The Simpsons." The story of Springfield being taken in by a charismatic conman was the brainchild of none other than Conan O'Brien, then a new writer on the show. Delivering such a strong episode helped establish him as a force to be reckoned with on the series, but he almost didn't even pitch it. Showrunners at the time, Al Jean and Mike Reiss, didn't think the idea for "Marge Vs. the Monorail" would fly with the show's co-boss, James L. Brooks, and told O'Brien to only pitch it if two of his other ideas didn't work. Ultimately, not only did Conan successfully pitch all three, Brooks absolutely loved the monorail idea.

Long before he became a late night legend, Conan O'Brien wrote for "The Simpsons" and produced some of the show's most beloved episodes. After leaving "Saturday Night Live," O'Brien received a call from Jean and Reiss, who asked him to join the animated comedy in its fourth season. The future "Late Night" host jumped at the opportunity and headed West. In a Vanity Fair Q&A, O'Brien recalled being incredibly nervous. "I was self-conscious," he said. "I was worried: 'Can I do it? Am I going to embarrass myself in front of these people?'"

He needn't have worried. According to Reiss, Conan successfully pitched three ideas during his first big staff meeting with Brooks, including the monorail idea which Reiss and Jean had previously dismissed as "too weird."

During its golden age, "The Simpsons" just couldn't miss. Even the "Simpsons" writers of today know they can't compete with classic-era episodes, so to create an instalment that stands out among such esteemed company is an especially remarkable achievement. That's exactly what Conan O'Brien did with "Marge vs. the Monorail."

The twelfth episode of season 4 saw sly salesman Lyle Lanley, voiced by the great Phil Hartman, descend upon Springfield just as the town came into a nice little windfall from Mr. Burns. After Lanley convinced everyone to invest in his monorail idea, the town was rejuvenated. But things very quickly went awry when the new transport system started to crumble due to Lanley's use of sub-par equipment. Also, Leonard Nimoy showed up for some reason and even teleported out of the episode in his final scene. It's an absolute classic, and likely the reason many a '90s kid grew up to call their pets "Bitey."

But the story behind one of the best episodes of "The Simpsons" begins with Conan almost being shut down before he could pitch it. In Vice's oral history of the show Mike Reiss spoke about the writers' annual retreat, where they would have "the undivided attention of [creator] Matt Groening and [co-developer/executive producer] James L. Brooks." As Reiss recalled, "We would prepare little pitches. Conan was brand new at the job and he came in with three ideas. He tested them on Al Jean and me first." Among these ideas was the monorail pitch, but the showrunners weren't sanguine about its chances of being greenlit. "When we heard about the monorail episode, we said, 'We don't think Jim Brooks is going to like this. We think it's too weird.'"

After hearing Conan O'Brien's monorail idea, Al Jean and Mike Reiss advised him to "put it in [his] back pocket" and not to pitch it unless he'd already tried his other two ideas. It was bad advice. Reiss continued, "It shows that we didn't know anything, because [James L.] Brooks loved the idea. Conan sold three script ideas at that meeting – his first meeting – and I don't think anyone had ever done that, before or since."

Actually penning the episode came fairly easy, with Conan's love of "The Music Man" helping him write "Marge vs. the Monorail." But another potential issue that turned out to be similarly easy to overcome soon arose. During a Vanity Fair interview, O'Brien recalled how Matt Groening was particular about "The Simpsons" following the rules of the real world as much as possible. As such, his idea to have Leonard Nimoy's teleport out of the episode initially caused concern:

"I remember there being a discussion with Matt [Groening], like, 'I don't think we can do this, 'cause this can't happen in the physical world.' I think Mike and Al had to pitch it to Matt or tell Matt, but Matt was okay with it, because [laughter] it was consistent with the 'Star Trek' reality. For whatever reason we got it, and I remember being happy about that."

Once again, Conan managed to pull off the unexpected with "Marge vs. the Monorail," which 33 years later still contains some of the funniest moments in "Simpsons" history.