In a 2020 interview with Staff Coco, O’Brien mentioned how he’d been introduced the anticipation to be the 3rd actor to play games conman Harold Hill within the 2000 Broadway revival. The function was once in the beginning taken up by way of Craig Bierko (“he was absolutely pitch perfect,” O’Brien famous) and nearest changed by way of Robert Sean Leonard in 2001. Someday in a while later this (O’Brien wasn’t sunlit at the precise timeline), O’Brien was once introduced the function.
“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 appeared much more disappointed concerning the ignored alternative, announcing, “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.”
At the dazzling facet, O’Brien did get to (form of) reach his dream in 2006, when he sang every other parody of “Ya Got Trouble” on the Emmys. This generation, rather of taking part in a man swindling a little the city, the music was once elevating consciousness concerning the many, many issues within the TV trade that might manage to a immense hit now not lengthy later on. O’Brien additionally were given to tick off every other bucket record merchandise in 2014 when he gave a are living live performance efficiency of “The Monorail Song.” It’s now not relatively the similar as attending to megastar in an entire Broadway display, however so far as a amusing full-circle day for O’Brien is going, it was once nonetheless good-looking cool.