Rise to Fame
His SNL audition was a celebrity impressions walk-a-thon that apparently made Lorne Michaels laugh, which people who've sat through auditions will tell you almost never happens. Tina Fey called him one of two people she'd seen who arrived completely ready. He co-hosted Weekend Update with Fey, became known for breaking character mid-sketch (notably in 'More Cowbell'), and left in 2004 for a film career that didn't click. NBC handed him Late Night in 2009 anyway, and the key move was pairing him with The Roots as his house band, which gave the show a hip-hop credibility that most late-night hosts never tried.
In the Spotlight
The Rolling Stone report in September 2023 gave the clearest picture of how the show actually operates. Sixteen staffers described 'good Jimmy days' and 'bad Jimmy days,' with moods volatile enough that employees started calling certain dressing rooms 'crying rooms.' Nine showrunners have cycled through since 2014. The ratings tell the rest: Colbert overtook him in 2017 and hasn't given the lead back, and the show now runs four nights a week. His 2016 hair-tousle interview with Trump is still the moment most people point to when explaining the slide.
Side Notes
Before SNL, he had one semester of college left and dropped out to move to LA for comedy. He'd also seriously considered becoming a Catholic priest. Neither path is as strange as what he's done with his downtime: seven children's books, a production company called Electric Hot Dog that produces That's My Jam and the Password reboot, and a New York real estate portfolio that started with a single apartment in 2002 on Lorne Michaels' advice and eventually became a 6-bedroom, 5,000-square-foot unit he listed for $15 million in 2021.