Stephen Colbert is set to bid farewell to his tenure on CBS’s *The Late Show* on May 21, 2026, marking the conclusion of an era that has spanned over ten successful seasons. As the host prepares to wrap up, he is reflecting on his journey, including the challenges faced during his inaugural episode in 2015 when he took over from the long-serving David Letterman.
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In a recent Q&A session shared on his YouTube channel, Colbert recounted the chaotic moments from that first show. He admitted that the transition from hosting *The Colbert Report* on Comedy Central to the far more complex environment of *The Late Show* was not without its hiccups. “Things were a little rough at first,” he recalled, noting that his team underestimated the intricacies involved in the CBS format.
Colbert vividly described a particularly trying moment in the editing suite where he found himself faced with a major technical glitch. Just minutes before airtime, the show was unable to export from the editing machine at a critical point during the opening monologue. “Every time we tried, it crashed at exactly 1:30,” he explained, highlighting the rising panic as the clock ticked down to the 11:35 p.m. start time.
As the minutes slipped away, Colbert felt the weight of the situation. “I’m thinking, ‘S—, somebody should tell the network,’” he shared, realising he was responsible for the show’s delivery. Despite assurances from the technical team that it would all work out, he could not shake the anxiety of potentially having the “shortest late-night career” in history.
With his family gathered for a watch party in New York City while he remained stuck in the seventh-floor editing suite, the pressure mounted. It was only when his editor, Jason Baker, proposed a quick solution—exporting directly to the broadcast centre—that a glimmer of hope emerged. Colbert, eager to ensure the show would reach its audience, made a dramatic move by kicking open a door to the accounting office in an effort to expedite the process.
Reflecting on this moment, Colbert described how a bottle of Old Forester bourbon was ceremoniously shared once the show successfully passed the critical 1:30 mark. “That moment is one of my fondest memories and also one of the most terrifying,” he said, recalling the tension leading up to that first broadcast moment. “I thought, ‘I might have the shortest late-night career,’ and indeed, I wasn’t sure if they’d let us do a second show if things went south on the first.”
Since that nerve-wracking debut on September 8, 2015, Colbert has hosted *The Late Show* for 11 seasons, becoming a prominent figure in late-night television. In July 2025, he announced that CBS had decided to cancel the show, a decision that the network described as a result of financial considerations amid a challenging landscape for late-night programming. Colbert expressed gratitude for the opportunity to host in such a “beautiful theatre.”
The cancellation of *The Late Show* was met with notable controversy, especially after Colbert spoke out against CBS’s parent company, Paramount, regarding a substantial settlement paid to former President Donald Trump. His criticisms highlighted the complicated relationships and dynamics within the media landscape.
As Colbert prepares for his final episode, he remains a beloved figure known for his quick wit and incisive commentary. The farewell broadcast is slated for Thursday, May 21, airing at 11:35 p.m. ET on CBS. Fans of the show are expected to tune in in droves to witness the conclusion of Colbert’s run, reflecting on the impact and legacy he leaves behind in late-night television.
In the coming weeks, Colbert’s departure will resonate not only with his dedicated fan base but also within the broader television community, as many reflect on the significant contributions he and his show have made to the genre. As he looks back on the journey, Colbert’s mix of humour and sincerity continues to resonate, ensuring his lasting impact long after the final credits roll.