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.
