In a revealing discussion on the MeSsy podcast with hosts Christina Applegate and Jamie-Lynn Sigler, former late-night comedian Conan O’Brien revisited a challenging chapter in his career. The episode, released in May 2025, focused on O’Brien’s emotional journey following his departure from The Tonight Show in 2010, which he described as a pivotal low point.
“I had no regrets about giving [The Tonight Show] a shot. And when, for all these complicated reasons, it blew up, I was deeply upset. I thought, ‘I’m in real trouble and this could be the end of my career [at 46],'”Conan shared on the podcast.
Despite the adversity he faced during this time, O’Brien highlighted the unexpected encouragement he received from a younger demographic on social media, which played a critical role in his recovery. Until that moment, he had not fully understood the extent of his influence on a generation raised on his comedic style.
Young Fans Rise to the Occasion — A Digital Groundswell
Conan O’Brien expressed gratitude for the spontaneous support that emerged from young fans during the fallout of his The Tonight Show exit. The comedian remarked:
“Lo and behold, this thing called the internet rose up, and I got this huge groundswell of love and appreciation that I didn’t expect,”he said.
Reflecting on his long tenure with Late Night, O’Brien likened it to “submarine duty,”admitting he hadn’t fully grasped the deep connection he had forged with viewers under 30. He articulated his surprise at the level of engagement online from a generation that had always been adept at utilizing digital platforms.
“You don’t get a chance to understand fully that there’s a generation of people out there that have been watching, they’re younger than me, and they all knew how to use the internet,” he noted.
This surge of online activity was dubbed a “wired army” by The New York Times, rallying behind O’Brien during his contentious negotiations with NBC over time slots. The personal and professional impact of such digital support profoundly influenced his understanding of audience engagement and internet culture, especially during a period when he feared that his television career was at an end.
Embracing Change—The Key to Resilience
During his conversation on the podcast, O’Brien discussed how his inherent restlessness and willingness to adapt significantly contributed to his comeback from the challenges faced at The Tonight Show.
“The one thing that saved me is I’m very restless, and I’m willing to change it up,” he explained.
Instead of committing to a decade-spanning career in late-night television, Conan O’Brien chose to pursue creative reinvention. He expressed his distaste for the conventional path in television:
“The idea of doing one thing for 35 years in television and getting a gold watch and leaving just sounded awful to me and still does,” he said.
With a chuckle, he added, “Although a gold watch would be great.” This mindset facilitated his ventures into varied formats, including his show on TBS, Conan, his travel specials, and his acclaimed podcast, Conan O’Brien Needs a Friend. Throughout these transformations, he embraced the challenge of engaging audiences through innovative approaches.
As the podcast progressed, O’Brien reminisced about his initial career milestones—from his days as a writer on Saturday Night Live and The Simpsons to taking up the hosting mantle from David Letterman. Each phase presented its own risks, but O’Brien recognized that embracing change and evolution has always been instrumental in his career trajectory.
Looking ahead, fans can catch the latest episodes of SNL, available for streaming on Peacock.