Few people have cast as large a shadow over the history of late-night television as Conan O'Brien. First bursting into the public eye as David Letterman's successor on "Late Night" in 1993, O'Brien hit pay dirt when he was tapped to replace Jay Leno as host of "The Tonight Show" in 2009. O'Brien's stint, though, was short-lived, marred by low ratings and NBC's ultimate decision to bring back Leno as host. O'Brien's final episode as "Tonight Show" host took place Jan. 22, 2010. He remained gracious and eloquent while signing off. "Please do not be cynical," hetold hisstudioaudience and viewersas he closed that final show. "I hate cynicism. For the record, it's my least favorite quality. It doesn't lead anywhere. Nobody in life gets exactly what they thought they were going to get. But if you work really hard and you're kind, amazing things will happen." Years later, he can look back and appreciate what he said. "I believe that still. Yeah. I think, man, who was that guy? That guy was smart," he joked to TODAY's Jacob Soboroff in a story that aired May 14. As wise as he may think those words were, O'Brien said he hasn't actually sat down and watched the clip. "No, never have," he said. "No. I can't do it," he continued. "It's too — I'm proud of it. But I can't — I don't — it was just a lot. It was a lot. And that was a moment where I really did think, 'I don't know. Maybe it's over for me.' I really did, you know?" O'Brien had an unusual route to fame. He worked as a writer on "Saturday Night Live" and "The Simpsons," but he was hardly a household name when he was chosen to take over for Letterman as host of "Late Night" when Letterman moved to CBS to host "Late Show." After initially struggling, O'Brien's "Late Night" became a fan favorite and ratings winner. O'Brien would remain with the program until 2009, when he took over for Leno as host of "The Tonight Show." O'Brien didn't last eight months on "The Tonight Show" and left following a messy, public split with NBC, but he would be just fine. In 2010, he returned as host of TBS' new late-night show, "Conan," which would run until 2021. He also went on to host the Emmy-winning shows "Conan Without Borders" and "Conan O'Brien Must Go," as well as his podcast, "Conan O'Brien Needs a Friend." In addition, he had a sort of full-circle moment when hereturned to "The Tonight Show"— now hosted by Jimmy Fallon — as a guest in 2024, hisfirst time on the programsince his exit almost 15 years earlier. Known for his trademark self-deprecating style, O'Brien in Marchreceived the Mark Twain Prize for American Humor, considered one of the most prestigious honors in comedy. Letterman presented him with the award. "I don't know that I'll have a more meaningful night in my career than I did at the Twain Award. It just had so much meaning for me," he said. "I'm so grateful to all those amazingly talented people that came. And it meant a lot to me that David Letterman was there. It meant the world to me," he added. O'Brien's career in comedy has been scrutinized, maligned and beloved. Still, he's grateful for how it all panned out. "I wouldn't change a thing, honestly. I know people say that, but I wouldn't change a thing," he said. "I've been insanely blessed. ... I've had all my dreams come true 75,000 times over. And even the dark moments have had gifts in them." It's all in line with who O'Brien is. "I like to make people laugh. I get a lot of joy out of making people laugh. And if, when we wrap this up and go and get coffee next door, if I can make the person at the counter laugh, I'm happy," he said. This article was originally published onTODAY.com
