Broadway Almost Brought A Beloved Simpsons Episode Full Circle For Conan O'Brien
A fun thing about getting into old musicals after watching "The Simpsons" your whole life is that you'll find yourself experiencing a never-ending string of realizations like, "Oh, so this is where that 'Simpsons' scene came from." Such is the case for "The Music Man," the 1962 musical about a conman who goes into a naive small town, stirs up a moral panic, and then uses said panic to sell them band instruments. This is all encapsulated in the musical number "Ya Got Trouble," where main character Harold Hill (Robert Preston) uses his charisma to get the town fully on board with his money-making scheme.
To a "Simpsons" fan, the song's tone, meaning, and rhythm should quickly feel familiar. That's because it's the same basic song Lyle Lanley (voiced by Phil Hartman) sings to the town of Springfield to get them to invest in a monorail they don't need. It's this song that kicks off the main plot of "Marge vs. The Monorail," and much like the town in "The Music Man," the Springfield residents prove themselves to be just as easy rubes as the conman's previous victims.
Although "Marge vs. The Monorail" was criticized at the time for being a little too random and silly, it's since earned a reputation as one of the best episodes in the whole show. The episode's writer, Conan O'Brien, is famous for it. Sure, most people know him as a late night host, but the word "monorail" is typically the first thing to come to mind whenever a "Simpsons" fan hears his name. That's why, when Broadway decided to revive the "Music Man" musical that the "Monorail" episode was based on, it's not a huge surprise that they asked O'Brien to star in it.
Not quite a fit, sadly
In a 2020 interview with Team Coco, O'Brien talked about how he'd been offered the chance to be the third actor to play conman Harold Hill in the 2000 Broadway revival. The role was originally taken up by Craig Bierko ("he was absolutely pitch perfect," O'Brien noted) and then replaced by Robert Sean Leonard in 2001. Sometime shortly after this (O'Brien wasn't clear on the exact timeline), O'Brien was offered the role.
"I found out that I couldn't do that and 'The Late Night Show' at the same time," he lamented, "So I was kind of heartbroken." In a 2022 interview with Adweek, he seemed even more upset about the missed opportunity, saying, "Man, if there's a world where I could come out, tag in and do the 'Trouble' song — I'm not sure I'm built for the whole musical — that would be my dream."
On the bright side, O'Brien did get to (sort of) achieve his dream in 2006, when he sang another parody of "Ya Got Trouble" at the Emmys. This time, instead of playing a guy swindling a small town, the song was raising awareness about the many, many problems in the TV industry that would lead to a massive strike not long afterward. O'Brien also got to tick off another bucket list item in 2014 when he gave a live concert performance of "The Monorail Song." It's not quite the same as getting to star in a whole Broadway show, but as far as a fun full-circle moment for O'Brien goes, it was still pretty cool.