Trump wanted to cancel a comedian. Instead, two comedians started canceling his legacy in real time.

Jimmy Kimmel says he was just in bed when it started. His wife walked out of the bathroom, phone in hand, and told him the President of the United States had just tweeted, “You should be fired again.” Not about a war. Not about policy. About a late-night host. At 12:49 a.m.

From there, the meltdown basically wrote itself.

Kimmel pulled up the post for his audience: Trump raging about “ABC fake news,” calling him talentless with “very poor ratings,” demanding networks “get the bum off the air.” Kimmel deadpanned: “I’m the bum.” Then pointed out the detail that hit hardest—Trump was watching the show live and celebrating his unemployment, along with hundreds of staff who lost their jobs in the temporary shutdown. A president gleeful about Americans being out of work. That, Kimmel said, is the exact opposite of what a leader should be.

Then Stephen Colbert picked up the baton. As the federal government officially shut down, he looked into the camera and delivered one of the most brutal lines of the night: “The Late Show has outlasted the United States federal government. We’re still open and they’re done.” The audience roared, but the point was deadly serious. Republicans blamed Democrats. Colbert spelled out the catch—the bill they wanted would strip health insurance protections and spike premiums for millions. It was like being forced to eat poisoned lasagna, he joked, then getting blamed for refusing dinner.

Together, Kimmel and Colbert turned Trump’s “businessman president” myth into a running gag. He said he’d run America like one of his companies—and suddenly you had a shutdown, threats to withhold SNAP benefits, and infrastructure funding used like a personal punishment weapon against New York City. Colbert mocked Trump’s plan to freeze billions in rail and subway projects just to strong-arm Democrats, calling it what it was: abuse of power dressed up as policy.

Visually, they put his taste and priorities on blast too. Viewers saw a before-and-after of the Oval Office—Biden’s simple, traditional setup versus Trump’s gold-soaked remake. Colbert compared it to Scrooge McDuck on bath salts. Trump bragged about “24 karat” additions and “world leaders freaking out” over the décor. The comedians flipped the script: no one was impressed. It looked less like the seat of a nation and more like a themed casino lobby with nuclear codes.

Kimmel then took aim at Trump’s obsession with applause and adoration. He replayed Trump whining that military leaders didn’t clap enough during his speeches, practically begging them to “do whatever you want” and leave the room if they didn’t like him. It was supposed to show strength, but under Kimmel’s lens, it screamed insecurity—a man who needs constant validation in rooms where respect is supposed to be earned, not demanded.

The takedown only got sharper when they touched his social media habits. Trump posted a racist video—a Black man in a sombrero with mariachi music—and called it comedy. Kimmel and Colbert shredded it as proof he can’t even keep his bigotry straight. It wasn’t just offensive. It was lazy, confused, and completely disconnected from the role of a president who’s supposed to represent everyone.

From there, they zoomed out and framed the bigger picture: a presidency that looks less like leadership and more like a never-ending open mic night. Trump bragging about “genius,” while stumbling through sentences. Declaring himself the greatest negotiator, while shutting down his own government. Claiming historic greatness, while picking fights over TV ratings, crowd sizes, and gold trim.

Kimmel’s verdict: Trump isn’t running a country—he’s hosting a show. Colbert’s add-on: and it’s a bad one. The plot lines repeat. The drama is recycled. The star is fragile and furious, but the audience has seen it all before.

The most devastating part of their joint roast isn’t the punchlines. It’s the pattern they expose. Trump wants monuments, airports, and history books to remember his “strength.” What he’s getting instead is something he can’t control: a growing archive of clips, monologues, and jokes that freeze his presidency in time as spectacle.

Kimmel and Colbert aren’t just mocking him for laughs. They’re writing the commentary history will play back. A president who wanted to look larger than life, slowly shrinking into the role he fears most—a joke everyone understands before he does.

And every time he tweets at them again, the script practically writes itself.