Stephen Colbert’s return to The Late Show on Monday night marked not only the resumption of political satire but also an opportunity for him to address one of the most bizarre and viral revelations from the newly released Epstein files — and he did so with a joke so filthy, so unexpectedly bold, that it brought the entire studio to a standstill of laughter, cheers and groans. While much of late-night television has been focused on Donald Trump’s ongoing reactions to the documents, Colbert took aim at a single email, one line long, but potent enough to ignite a storm of commentary online. And he used it to craft a punchline that instantly entered the canon of his most outrageous jokes.

Colbert began by noting that Donald Trump’s name appeared roughly 1,600 times in the documents — a detail delivered with his signature deadpan, allowing the weight of the number to land on the audience. But the real material, Colbert said, came from a 2018 email written by Mark Epstein, brother of the late Jeffrey Epstein, containing a now-infamous line: “Ask him if Putin has the photos of Trump blowing Bubba.” Colbert paused, letting the sheer absurdity of the wording sink in, before raising the question that had been circulating online for days: “Who is this lucky Bubba?” His mock curiosity drew immediate laughter, playing on the crudeness of the phrase while opening the door to a more pointed joke.

Many, including political commentators and internet sleuths, quickly connected “Bubba” to former president Bill Clinton, who has long been associated with the nickname. But Colbert explained that Mark Epstein had since issued a formal statement denying the Clinton connection, calling the email “a humorous private exchange” and insisting that any attempt to link the line to Clinton “misrepresents both the purpose and the tone of the original correspondence.” Colbert couldn’t resist mocking the overly polished and self-serious clarification. He booed loudly on behalf of the audience, stretching the jeer for comedic effect. “Booo! Booo! Mark, let us have a silly one!” he shouted, embracing the collective sentiment that Epstein’s attempt to sanitize an already absurd email was unnecessary and humorless.

Colbert then acknowledged that The Late Show had unfortunately been off the air when the story first broke, meaning he never had the chance to take an immediate comedic swing at the viral moment. Monday night gave him his first opportunity — and he made sure it counted. He stepped forward, dramatically set up the punchline and delivered one of the filthiest, sharpest jokes of his career: “Now we know how Trump got a taste for politics.” The audience erupted. The reaction went on for nearly 15 seconds — a rare moment in late-night when a joke doesn’t just land, but detonates. Some people cheered, others laughed uncontrollably and plenty groaned loudly at the boldness of the line, proving Colbert had struck the exact balance he aimed for: shocking, smart and scandalously on topic.

The joke worked not only because it was risqué but because it tapped into the surreal public fascination with the Epstein emails, where political figures, speculation and dark humor have collided into a cultural flashpoint. Colbert’s delivery, full of mischievous confidence, allowed the audience to release days of pent-up reactions to the headline. He framed the moment as something absurd rather than purely scandalous — acknowledging the seriousness surrounding the Epstein files but also carving out space for comedy where the ridiculousness of the content demanded it.

Colbert’s ability to navigate such volatile material with comedic precision has long been one of his greatest strengths. In this case, he didn’t minimize the context or implications of the documents; instead, he zoomed in on a line so bizarre that treating it with pure seriousness would have made it even stranger. His laughter and the audience’s extended reaction spoke to a collective desire for levity in the midst of politically heavy headlines.

By the end of the segment, Colbert had accomplished something late-night hosts strive for: he managed to take a deeply controversial and troubling news event and carve a comedic moment that resonated widely, sparked conversation and showcased his trademark blend of wit and irreverence. The joke may have been filthy — arguably one of the filthiest he has told on The Late Show — but it also demonstrated his ability to capture the cultural mood with a single punchline. And in a news cycle dominated by scandal, speculation and political chaos, Colbert’s humor offered a momentary release, proving once again why he remains one of late-night television’s most compelling voices.