Where did this weird idea come from? The idea of a con man bilking Springfield out of millions of dollars seems like a fine idea for a “Simpsons” story, but why a monorail? “Marge vs. the Monorail” was also clearly inspired by “The Music Man.” Was Conan O’Brien a fan, or was he merely fond of the structure? According to showrunner Mike Reiss, O’Brien was still something of a “new kid” on the show, and the entire episode was his idea. Reiss and co-showrunner Al Jean heard O’Brien’s pitch (at a special writers’ retreat) but were concerned that show creator Matt Groening and executive producer James L. Brooks wouldn’t like it. They were wrong. Brooks loved it. Indeed, Reiss recalls that O’Brien successfully pitched three script ideas during the writer’s retreat.
Story editor Josh Weinstein recalled O’Brien as being energetic and “up” all the time. “Working with Conan was like watching a ten-hour episode of his show, every day, in the writers’ room,” he said. “All the other writers are hilarious, but most of them are quiet and thoughtful, whereas Conan’s just out there.”
As for the “Music Man” thing, that was all O’Brien. Producer Jeff Martin, in the Vice oral history, noted that O’Brien turned in the lyrics and his was his job to make it musical:
“Every single word of the monorail song was unchanged from Conan’s first draft, which is impressive. My niche on the show in those days was to actually write the tunes to the songs. I wrote a bunch of songs, so I was assigned to set the monorail song to music. It’s sort of like, ‘Bum, bum, bum, bum. I think I’m done!’ It’s barely a song. It’s just sort of a rhythm and ‘Monorail! Monorail! Monorail!'”
Mono– D’oh!