Stephen Colbert’s Last Laugh: CBS’s Late-Night Star Turns His Wit on His New Boss and the Network That’s Letting Him Go

In an era when late-night comedy doubles as public commentary, Stephen Colbert still knows how to turn resignation into a punchline.

On Thursday’s Late Show, the CBS host—whose run is set to end next May—used his monologue to deliver a well-timed roast of his new boss, David Ellison, marking National Boss’s Day with a wink that managed to be both hilarious and hauntingly self-aware.

“I want to take a moment to celebrate my new boss, Paramount CEO David Ellison,” Colbert said, peering into what he called his ‘David Ellison Appreciation Cam.’
“Mr. Ellison, I love you.”
Then came the wink: “That oughta buy us a couple more months.”

The audience erupted. Beneath the laughter, though, was an unmistakable sting.

A Comedian Without a Company

Colbert’s jab came just weeks after CBS announced it would end The Late Show at the conclusion of the 2025–26 season, citing “financial restructuring” following Paramount’s merger with Skydance Media, Ellison’s entertainment empire.

For the Emmy-winning host, the timing is almost poetic. A fixture of late-night since his Colbert Report days, he now finds himself adrift in the same corporate tide that’s reshaping the industry he’s spent decades satirizing.

Ellison, the son of billionaire Oracle founder Larry Ellison, became CEO of the newly formed Paramount Skydance after finalizing the merger in August. The deal—valued in the billions—gave the 41-year-old producer unprecedented influence over some of America’s most storied entertainment brands: Paramount Pictures, CBS, Nickelodeon, and MTV among them.

But it also came at a cost.

The Price of a Merger

The merger closed only a month after Paramount reportedly paid $16 million to settle a lawsuit from former President Donald Trump, stemming from his claim that CBS’s 60 Minutes “rigged” a 2024 interview with then–Vice President Kamala Harris. The case, legally dubious but politically potent, hung like a cloud over the company’s attempt to secure regulatory approval for the Skydance deal.

When the settlement hit the news, Colbert didn’t mince words—turning his monologue into a rare act of on-air insubordination.

“I believe this kind of complicated financial sentiment with a sitting government official has a technical name in legal circles,” Colbert quipped.
“It’s big fat bribe.”

The audience gasped, then laughed, then applauded. But the point was clear: Colbert was accusing his own network of bending to political pressure.

Behind the humor was a genuine critique—one that many media observers shared. “It’s not often you see a late-night host publicly implicate their employer,” said media analyst Joseph Alvarado. “It’s a testament to how unsettled things are at CBS, and how much Colbert feels he has nothing left to lose.”

David Ellison and the Battle for CBS

For Ellison, inheriting CBS means inheriting its turmoil. The merger that made him one of Hollywood’s youngest moguls also left him in charge of a news division and a late-night institution now accused of caving to political and corporate pressure.

And the controversy hasn’t stopped there. Earlier this month, Paramount Skydance purchased the independent outlet The Free Press and appointed its founder, Bari Weiss, as the new editor-in-chief of CBS News—a move that sent shockwaves through both journalism and entertainment circles.

Critics on the left decried the appointment as another step in the consolidation of corporate media power under ideological banners. Supporters praised it as a shake-up for an industry they say has grown too homogenous. Either way, Colbert’s jokes landed in a moment when CBS’s identity—and integrity—seem up for grabs.

The End of an Era in Late-Night

The end of The Late Show with Stephen Colbert marks more than a programming change; it symbolizes a shift in the cultural center of gravity for American comedy. Colbert’s show, with its blend of satire and sincerity, has served as one of the last bastions of politically literate late-night television in an era increasingly driven by streaming, short clips, and algorithmic engagement.

“Colbert is part of the old guard,” said television historian Marisa Trent. “He came from a world where television was still the hearth of the nation—where you could make fun of politics and still believe politics could matter.”

Now, the landscape is splintered. Viewership is down across the board. Attention spans are shorter. Late-night’s once-sharp political edge has dulled against the endless scroll of social media outrage.

In that context, Colbert’s humor feels almost defiant—an act of resistance from a performer who understands both his audience’s cynicism and his own obsolescence. When he looked into the camera Thursday night and professed mock love for Ellison, the joke wasn’t just about sucking up to the boss. It was about the absurdity of pretending sincerity can survive inside a corporate machine that rewards conformity.

A Laugh That Echoes

Colbert’s gift has always been his ability to use comedy as camouflage—to wrap truth in absurdity, to make confrontation sound like charm. That skill has never been more necessary. As CBS pivots toward consolidation and cost-cutting, his monologue doubled as an epitaph for the version of television he represents: intelligent, human, and unafraid to bite the hand that feeds it.

His parting wink—“That oughta buy us a couple more months”—was more than a throwaway punchline. It was an elegy for late-night independence, delivered with the poise of a man who’s seen this story before and knows exactly how it ends.

The Future According to Colbert

There’s a certain irony in watching one of America’s most incisive satirists go out under the leadership of a studio head known for action franchises and blockbuster ambition. But if Colbert’s final season becomes his swan song, it may also be his most liberated.

Freed from the need to please advertisers or appease executives, he can afford to tell the truth—as only a comedian can.

“Colbert’s humor has always come from moral clarity,” said Trent. “He’s the rare comic who makes you laugh and think at the same time. If this really is the end, he’s going out the way he came in: fearless, sharp, and with the last laugh.”

And so, as CBS’s late-night era draws to a close, one thing is certain: Stephen Colbert may be losing his stage, but he’s keeping his voice. And for now, that voice still cuts through the noise—with a wink, a smirk, and one perfectly timed line.