Bob Costas, the renowned sportscaster, has recently reflected on his early impressions of Conan O’Brien during the comedian’s initial foray into late-night television. The two media figures shared a network in the early 1990s, with O’Brien succeeding David Letterman in NBC’s late-night slot in 1993, just before Costas began hosting his own show, “Later with Bob Costas,” later that same year.
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In a discussion on “The Friars Club Podcast,” which was reposted on Nostalgia Tonight, Costas candidly recounted his initial reservations regarding O’Brien’s potential success in the new role. The legendary broadcaster, now aged 74, admitted that he did not foresee O’Brien, now 63, becoming an iconic figure in late-night television at that time due to his lack of experience in front of the camera.
Costas had the opportunity to observe O’Brien’s transition from a talented comedy writer to a television host. He acknowledged that while O’Brien possessed a unique sense of humour and intelligence, it was evident during those early days that he struggled with the nuances of performing live. “There was no question that he was funny and there was no question that he was smart,” Costas remarked. However, he noted that O’Brien’s nervousness often shone through during his first performances.
The veteran broadcaster expressed gratitude that NBC had the patience to support O’Brien through this adjustment period. Costas cited this key decision as pivotal, suggesting that O’Brien’s distinct comedic style might have been lost if the network had chosen to end his show prematurely. “If NBC had not been patient with him, we would have lost out on one of the greatest ever in late night,” Costas explained, highlighting the importance of allowing creative individuals the space to grow into their roles.
Reflecting on O’Brien’s early performances, Costas conveyed that there were moments when he felt uncertain about the future of the show. “To be honest with you, I didn’t know how many more shows there would be,” he confessed, underscoring the challenges O’Brien faced as he found his footing. Over the years, however, O’Brien evolved and developed a unique style that resonated with audiences, ultimately becoming a staple in the world of late-night entertainment.
Conan O’Brien’s late-night career spanned nearly three decades, during which he hosted over 2,000 episodes of “Late Night with Conan O’Brien” from 1993 to 2009. Following this, he led “The Tonight Show with Conan O’Brien” for a brief period before moving to TBS, where he hosted “Conan” from 2010 to 2021.
Currently, O’Brien is entertaining audiences with his travel series, “Conan O’Brien Must Go,” which has recently returned for its third season on HBO Max. This new show serves as a spinoff from his podcast, “Conan O’Brien Needs a Friend,” further showcasing his adaptability and relevancy in the ever-evolving landscape of entertainment.
In a 2026 interview with The New Yorker’s David Remnick, O’Brien elaborated on the freedom he now enjoys to express himself creatively across various platforms. He remarked that the traditional late-night format is fading, giving way to innovative ways to connect with audiences. O’Brien noted, “There’s a lot of really beautiful opportunities,” embracing the diversity of formats that allow him to showcase his talent and sense of humour.
O’Brien’s journey from uncertain newcomer to a beloved figure in late-night television serves as a testament to the importance of resilience and support in the creative process. His evolution as a host continues to inspire a new generation of entertainers, as he navigates the ever-changing media landscape with wit and charm. As Costas observed, O’Brien’s unique comedic voice has left an indelible mark, solidifying his place among the greats in the history of late-night television.