Entertainment
Conan O’Brien Still Won’t Watch the Moment His ‘Tonight Show’ Era Ended
When most people think about late-night talk shows, chances are they think of hilarious celebrity moments, funny maybe even cringe-worthy segments and a host that’s both entertaining and naturally charismatic. But while that might be true for these shows most of the time, late-night talk shows have also generated some major drama between their hosts. Most notably, things quickly soured between Jay Leno and Conan O’Brien in 2009 after O’Brien’s sudden exit from NBC.
It all began when, after hosting The Tonight Show for 17 years, Leno moved to an earlier timeslot and O’Brien finally became the host of The Tonight Show, a role he’d worked so hard and long for. O’Brien’s tenure on the seat, however, didn’t last long. After only seven months, ratings of his show and Leno’s were worrying NBC, and they pushed for a new schedule that had O’Brien’s show to 12:05 a.m. O’Brien objected to the after-midnight time slot, and NBC reached a settlement with him to end his contract. The decision was heartbreaking to O’Brien and his longtime fans. Not only did he just reach a major career milestone he worked so hard for, but it seems he never got the chance to fully give it a go. To this day, it’s still a sore subject for the host.
The End of His Talk Show Still Hits a Nerve
In a May 2025 interview with O’Brien on the Today Show, Jacob Soboroff sat down with O’Brien and asked if he ever saw his sendoff from The Tonight Show, which aired on February 20, 2009. “No, I can’t do it,” O’Brien said simply. “I’m proud of it, but I can’t. It was just a lot.” He then reflected on where his mindset was at the time. “That was a moment where I really did think, ‘Maybe it’s over for me,’” he said. At the time, O’Brien wasn’t shy about his grievances. “It was my mistaken belief that, like my predecessor, I would have the benefit of some time and, just as important, some degree of ratings support from the prime-time schedule,” O’Brien said in a statement, per CBS News. “But sadly, we were never given that chance.” After O’Brien’s departure as host, Leno resumed his hosting duties on The Tonight Show, a role he continued until 2014. Therefore, not only was the dream of hosting the prestige timeslot swiftly taken from O’Brien, but it was clear that NBC chose Leno over O’Brien, which ignited a feud and left fans up in arms.
At the time, fans immediately reacted to the host change-up. Fans cheering for “Team Conan” made it a major Twitter trend, and the “I’m With Coco” image went viral, and more than a million people joined the two major Facebook groups supporting him. Fans took their outrage to the streets too, with “I’m With Coco” rallies in Los Angeles, New York, Chicago and Seattle, many wearing orange in honor of O’Brien’s hair. At the Los Angeles rally, O’Brien himself even showed up and spoke with the crowd. In 2010, Leno also added fuel to the fire by admitting to his role in the situation. Speaking about the best prank he’s ever pulled on The Tonight Show with Jimmy Kimmel, he said, “I told a guy that five years from now I’m going to give you my show, and then when the five years came, I gave it to him, and then I took it back almost instantly.”
Of course, while O’Brien’s departure, and Leno’s attitude towards the situation, angered fans, O’Brien’s show wasn’t perfect either. After all, in the years prior to his time on The Tonight Show, O’Brien stood out because he was openly weird, self-deprecating, and often deliberately anti-polished. Unlike traditional late-night hosts in the past, O’Brien was kooky, different, and unapologetically himself. But, when he moved to NBC’s most prestigious late-night institution, his unique form of comedy was tested. The ratings expectations changed, the audience for the show changed, and, in turn, ratings started to dwindle. Seven months later, NBC pulled the plug.
O’Brien Has Been Reinventing Himself Ever Since
But while O’Brien’s departure from The Tonight Show had him questioning his career, he’s been producing great content and growing his fanbase ever since. His next step after leaving NBC was hosting Conan on TBS, and ran for an impressive 11 years. In the meantime, he also stepped outside his desk and hosted the Emmy-winning Conan Without Borders travel specials and his hugely successful podcast, Conan O’Brien Needs a Friend. Soon enough, Team Coco grew into a larger digital comedy brand before being acquired by SiriusXM in 2022, and the podcast has since surpassed 660 million downloads.
His career reinvention continued to pay off when he hosted Conan O’Brien Must Go, a travel series that turned the Without Borders concept into a full-fledged hit and is now in its third season. O’Brien also made his major awards show host debut at the 2025 Oscars, bringing in 19.69 million viewers, its highest audience in five years. He returned to host again in 2026, and is already set to return for the 99th Academy Awards on March 14, 2027. He was also inducted into the Television Academy Hall of Fame in 2025.
Ultimately, while perhaps no career success could make up for the heartbreak that was losing The Tonight Show in 2009, Conan O’Brien has been steadily making a name for himself outside the scandal ever since. While his departure was painful, his more untraditional career path became a remarkably successful second act, one that guaranteed he always had the freedom to be himself.
- Release Date
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April 18, 2024
- Network
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HBO, Max
- Directors
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Mike Sweeney
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