Stephen Colbert Celebrates 10 Years of The Late Show with Jokes About Trump, Epstein, and a Cowboy Sex Scandal

Stephen Colbert marked the 10th anniversary of The Late Show with exactly what fans expected — razor-sharp humor, savage political jabs, and a little bit of chaos.

“Welcome one and all to The Late Show,” Colbert began, before reminding the audience that they weren’t just watching another Monday night episode. “Tonight is the 10th anniversary of The Late Show. Of course, every anniversary has its traditional gift. First anniversary is paper, the fifth is wood, and the 10th anniversary… is cancellation.”

It was classic Colbert: self-deprecating, quick-witted, and just a little bit cheeky. “It doesn’t feel like 10 years,” he said. “Except for how I feel and how I look.” He even compared a photo of himself from 2015 to now, joking about the “toll time takes.”

But Colbert didn’t linger on nostalgia for long — the rest of the monologue was all about the wild state of the world, Donald Trump’s latest antics, and even a bizarre scandal involving cowboy-themed erotica.

Trump’s “Department of War” Rebrand

Colbert’s first target of the night was former President Donald Trump, who signed an executive order rebranding the Department of Defense as the “Department of War.”

“Trump explained his reasoning,” Colbert said. “He claims we ‘went woke’ when we changed the name during the Truman administration. You know, that famously woke era — the same one that dropped the atomic bomb.”

Colbert pointed out that Trump can’t technically rename the department without congressional approval, so the new title is really just a secondary nickname. “Government agencies can’t have nicknames,” Colbert quipped. “Remember when NASA tried to get everyone to call them Big Dog? No one wants to hear ‘Big Dog, we have a problem.’”

He also mocked Trump’s online posts celebrating the change, including one where Trump portrayed himself as a character from Apocalypse Now. “Check out Colonel Bone Spurs,” Colbert joked, suggesting the image was AI-generated because “if Trump ever crouched like that, his cankles would pop like water balloons.”

Jeffrey Epstein’s “Birthday Book”

From there, Colbert pivoted to the resurfacing of Jeffrey Epstein-related revelations. Congressional investigators reportedly obtained Epstein’s “birthday book,” which included well-wishes from high-profile friends — and even a controversial letter allegedly from Trump.

Colbert reminded viewers that earlier reports suggested Trump had drawn a crude image of a naked woman and signed it in a very questionable way. Trump denied the allegation at the time, insisting, “I don’t do drawings of women.”

“That’s interesting,” Colbert deadpanned, “because he didn’t just deny it — he sued Rupert Murdoch and the Wall Street Journal for $10 billion. Well, now Murdoch must be laughing up in heaven — wait, what? Does he know that?”

The audience roared as Colbert compared the situation to the theme song of Friends: “So no one told you you were on a pervert’s plane — oh wait, they told you, and you still got on his plane.”

Nantucket’s Cocaine Problem

In one of the night’s strangest pivots, Colbert brought up a report claiming that Nantucket’s sewage showed cocaine levels 50% above the U.S. average.

“Of course,” Colbert joked, “we all know the famous limerick: There once was a man from Nantucket who bought his cocaine by the bucket…”

The crowd erupted as he continued with a ridiculous rhyme about DJs, skydiving, and losing track of the cocaine.

The X-Rated Cowboy Story Scandal

The monologue ended with a story that sounded like it came straight out of late-night fiction: a Trump administration appointee is under fire for writing a sexually explicit cowboy romance.

“This isn’t some cute romcom,” Colbert said, before describing the book’s graphic scenes and imagining how awkward it must have been when the author shared the story with colleagues.

“How do you respond when your coworker shares his cowboy porn with you?” Colbert asked, before delivering one of the night’s best punchlines: “Feels like the campfire orgy scene could have been an email. Hope this finds you in HR.”

A Decade of The Late Show

Colbert closed by teasing more anniversary surprises, promising a look back at “the last 10,000 years of The Late Show” and welcoming guests Cillian Murphy and Lady Gaga.

Ten years in, Colbert is still delivering what made him a household name: smart political satire, pop culture riffs, and just enough absurdity to keep things unpredictable.