Stephen Colbert’s final night on the air is May 21, closing a run that made The Late Show With Stephen Colbert one of the defining political voices of late-night television. For years, Colbert has been the ferocious, incisive and witty critic of President Trump who sat at the center of a genre that increasingly behaved like an opposition party.
That is why he belongs on any hypothetical Mount Rushmore of late-night cultural impact, alongside Johnny Carson, David Letterman and Jon Stewart. Colbert and Stewart refined the art of comedy-as-commentary, and Colbert became the de facto leader of late-night’s opposition party during the Trump years.
The arc was already there long before Trump returned to the center of American politics. Colbert first became famous by playing a right-wing blowhard on Comedy Central’s The Colbert Report, a performance that let him skewer power by inhabiting it. By the time he inherited The Late Show, he had turned that instinct into something broader: a host who could turn a joke into an argument and a punch line into a kind of civic warning.
In 2008, on Election Night, he appeared to tear up when Stewart announced that Barack Obama had been elected. Eight years later, after Donald Trump’s stunning victory in 2016, Colbert showed a photo of the middle school where he had voted earlier that day and told viewers, “Regardless of the outcome of the election, this is still a beautiful place and a beautiful thing that happened today.” The next night, he was even more raw. “I’m not sure what to believe about anything anymore,” he said. “How’s everybody doing right now? How are you feeling? … I’m so glad to be with you tonight. I wouldn’t want to be alone right now.”
He also gave his audience a message that sounded less like a monologue than a plea for moral steadiness: tell children to work hard, be kind, care about other people, don’t be selfish, don’t grab them where they don’t want to be grabbed, and they’ll make the world a better place than Trump can. That line captured what made Colbert’s politics feel different from the usual late-night reflex. He punched up, never down, and his comedy was grounded in empathy, rooted in who he is and what he values.
There was another layer to that empathy. In 1974, when Colbert was 10, his father and two of his brothers were killed in a plane crash. In 2022, on Anderson Cooper’s podcast, he said he was eventually “grateful” for the grief he experienced. That history helps explain why his voice on television often felt less like a performance of outrage than an attempt to make sense of loss, fear and political absurdity without surrendering to any of them.
So when he signs off on May 21, the question is not whether late-night will keep going. It will. The real answer is that one of the era’s most consequential hosts is leaving after helping redefine what the format could be in an age when comedy and political opposition became almost indistinguishable.
