After a late-summer break, The Late Show with Stephen Colbert stormed back onto TV screens on September 3, and Colbert wasted no time picking up where he left off: skewering President Donald Trump with sharp wit and razor-edged jokes.

The late-night host, who is now in the final season of his CBS show, didn’t just comment on headlines — he turned them into punchlines. From Trump’s plans to host the Kennedy Center Honors to his controversial remarks about Chicago, Colbert made it clear that he’s using his remaining months on The Late Show to go out swinging.

And perhaps the most biting joke of the night? A perfectly timed troll about Trump’s latest “comeback” gig that doubled as a sly nod to Colbert’s own show’s cancellation.

Trump’s Surprising Hosting Role

The biggest headline on Colbert’s radar was Trump’s announcement that he will serve as the host of the Kennedy Center Honors on December 7, 2025. The ceremony, traditionally a celebration of artistic excellence, has never been helmed by a sitting president. Trump’s decision to step into the role immediately sparked controversy — and gave Colbert the comedic opening he needed.

“Another sign that Trump has gone full autocrat,” Colbert told his audience, “he recently made himself the chair of the Kennedy Center and then, as chair, found the perfect host for this year’s Kennedy Center Honors: himself.”

The crowd booed at the mention of Trump’s decision, but Colbert turned it into a laugh. “You’re the most powerful man on Earth. What are you doing? You’re the most powerful man, and all you want is a hosting gig? Those don’t last as long as they used to, buddy!”

Then came the kicker: Colbert pointed to himself, referencing Paramount and Skydance’s merger and the resulting cancellation of his own show. The audience erupted in laughter and applause. It was the kind of self-aware, layered joke that has defined Colbert’s late-night run.

A Self-Aware Roast

The brilliance of Colbert’s joke wasn’t just in its punchline. By comparing Trump’s hunger for a “hosting gig” with his own soon-to-end tenure on CBS, Colbert managed to poke fun at both the president and himself.

It was a reminder that Colbert’s comedy often works best when he brings himself into the joke. In this case, the laugh wasn’t just about Trump’s ego — it was about the absurdity of power, fame, and the strange business of television itself.

And as Colbert enters his show’s final season, that willingness to poke fun at his own circumstances is making his monologues sharper, freer, and more unpredictable.

“I Was Begged”

Colbert also mocked Trump’s claim that he didn’t want to host the Kennedy Center Honors, but was “begged” to do it. A clip of Trump making the claim was played, where he insisted that people told him he would deliver “high ratings.”

It was vintage Trump — conflating leadership with television viewership — and Colbert seized on it. “High ratings as the president,” he scoffed, setting up the absurdity. After all, Colbert himself knows a thing or two about chasing ratings in the ever-shifting late-night landscape.

The moment captured one of Colbert’s greatest strengths: the ability to use Trump’s own words as comedy ammunition, exposing the irony without even needing to exaggerate.

Defending Chicago

But Colbert’s monologue wasn’t only about Trump’s hosting gig. He also addressed the president’s plan to deploy National Guard troops to Chicago, a decision Colbert described as “a hard right onto the fascism freeway.”

Trump had labeled Chicago a “hellhole” and, in a social media post, the “worst and most dangerous city in the World, by far” and “the murder capital of the world.” Colbert wasn’t having it.

“Two words: F— you,” Colbert shot back, defending the city.

Chicago holds special meaning for Colbert, who graduated from Northwestern University and cut his teeth in comedy at the legendary ImprovOlympic theater. To underline his connection, he capped his rant by taking a shot of Malört — the notoriously bitter Chicago liqueur that has become a badge of honor for locals.

It was a classic Colbert move: mixing sharp political critique with personal history and just enough theatricality to bring the house down.

The Health Rumors

Colbert also briefly touched on the swirling rumors about Trump’s health that spread across social media over Labor Day weekend. While he didn’t devote as much time to the speculation as he had to the Kennedy Center and Chicago stories, he couldn’t resist throwing in a few digs.

His framing was simple: in an age when conspiracy theories spread faster than facts, sometimes the only way to address them is to make the rumor itself the punchline.

Gloves Off in the Final Season

What made Colbert’s monologue especially fiery was the context. With The Late Show slated to end in mid-2026, Colbert no longer has to play it safe. Instead, he seems determined to use every remaining episode to speak his mind, sharpen his satire, and tackle the headlines without pulling punches.

For viewers, that makes his final season must-watch TV. Colbert isn’t coasting to the finish line — he’s leaning in, treating each episode like an opportunity to deliver the kind of biting comedy that made him a household name.

Why the Hosting Gig Joke Worked

Among all of Colbert’s jokes, the troll about Trump’s Kennedy Center role stood out because it worked on multiple levels:

It mocked Trump’s ego, highlighting how strange it is for a sitting president to chase a hosting gig.

It drew a parallel to Colbert’s own career, making the joke self-aware and layered.

It resonated with viewers, many of whom are still processing the end of The Late Show.

By weaving together personal commentary and political satire, Colbert delivered a monologue that felt both timely and timeless — a hallmark of his late-night style.

Looking Ahead

As Colbert’s final season rolls on, fans can expect more of the same: sharp humor, unflinching critiques, and a sense that the gloves are well and truly off.

With Trump continuing to dominate headlines, Swift and Kelce’s engagement sparking endless pop culture chatter, and late-night itself undergoing major shifts, Colbert has no shortage of material. And if his first show back is any indication, he’s ready to tackle it all with the same biting wit that’s defined his career.

The Last Word

“Hosting gigs don’t last as long as they used to, buddy,” Colbert said, looking straight at the camera after skewering Trump’s Kennedy Center announcement. It was a line that cut two ways — mocking Trump while slyly winking at his own situation.

That’s the magic of Colbert at his best: humor that’s funny in the moment but also laced with deeper resonance.

As he heads into his last season, Colbert seems determined to leave audiences laughing, thinking, and maybe even a little rattled. And with Trump back in the headlines, the punchlines aren’t going to stop anytime soon.