Most of America is asleep.
But Donald Trump isn’t.
He’s in his private suite, TV blaring, thumbs flying across his phone as he rage-posts on Truth Social — because two late-night comedians just spent another night shredding his lies on national television.
Jimmy Kimmel. Stephen Colbert.
The two names that live rent free in Trump’s head.
He calls them “no-talent losers,” demands they be fired, hints they should be punished for “illegal campaign contributions” in the form of jokes. But every time he comes for them, they only get bigger, louder, and more dangerous — to him.
Because they’re not just telling jokes.
They’re building a record.
They’re archiving his lies, exposing his schemes, and turning his so-called “strongman” image into a punchline that millions of Americans share before bed.
The Night the Jokes Cut Deeper
On this particular night, everything collides at once.
Congress has just voted 427–1 to release the Jeffrey Epstein files — a landslide so huge, Jimmy Kimmel jokes that Trump might be able to “re-bury the files under it.” Trump had spent months trying to block that vote. Now he’s claiming he “always wanted maximum transparency” and that the bill only passed because he asked for it.
It’s classic Trump: lose, then pretend it was your plan all along.
Kimmel isn’t buying it. He calls out the shameless spin, the gaslighting, the way Trump threatens to starve poor Americans and gut healthcare subsidies while pretending he’s their savior. He runs down the list:
– ACA premiums set to jump by 26%
– Enhanced subsidies expiring
– Millions heading into the holidays with more debt and less coverage
Trump’s answer?
No real plan. Just vague promises and a demand for praise.
On Fox Business, Trump’s favorite “experts” scold Americans for complaining about grocery and gas prices. Kimmel mocks them as overpaid hedge-fund crybabies who lost money in a bull market and now want working families to “stop whining.”
The audience roars.
Trump seethes.
Colbert, the Prictator Slayer
Then there’s Stephen Colbert — the man who’s been poking Trump’s ego with a sharp stick for nearly a decade.
He was fearless before Trump ever ran for president. Back in 2006, he roasted George W. Bush to his face at the White House Correspondents’ Dinner while the room froze. But 2017 brought something else entirely.
When Trump insulted CBS host John Dickerson and called his show “Deface the Nation,” Colbert snapped. He went on air and unleashed one of the most infamous monologues in late-night history. He called Trump “the glutton with the button,” “Gorge Washington,” and said the only thing Trump’s mouth was good for was being “Vladimir Putin’s cockholster.”
The FCC opened an investigation. MAGA world demanded he be fired.
Colbert came back the next night and said, “I have jokes. He has the launch codes. It’s a fair fight.”
That’s the difference.
Trump threatens. Colbert doubles down.
Trump’s Revenge… and the Backfire
Fast forward to 2025.
Trump is back in power and using his office like a weapon. He pushes loyalists into key positions, pressures networks, and tries to punish his critics by targeting their employers.
When CBS agrees to pay Trump $16 million to settle a lawsuit over a 60 Minutes interview, Colbert calls it what everyone knows it is: a payoff. Shortly after, CBS cancels The Late Show.
Trump rushes to Truth Social, gloating:
“I absolutely love that Colbert got fired. His talent was even less than his ratings.”
But this time, the backlash doesn’t hit Colbert. It hits Trump.
Outside the Ed Sullivan Theater, protesters gather with “Colbert Stays, Trump Must Go” signs. Senator Elizabeth Warren calls for an investigation into whether the cancellation was politically motivated. The Writers Guild blasts it as corporate cowardice and a bribe for access.
Colbert goes on air, looks directly into what he calls “the eloquence cam,” and says one simple message to the president:
“Go [__] yourself.”
The crowd explodes.
And then, just to drive the point home, Colbert wins his first Emmy for Outstanding Talk Series.
Trump tried to erase him.
Instead, he upgraded his legacy.
Why Trump Can’t Stop Watching
This is why Trump stays up past midnight doom-scrolling Kimmel and Colbert clips.
Kimmel reads Trump’s unhinged manifestos about the Epstein files and responds with a simple “I do not have the time to read all that, bro.” He exposes the fake “Black Friday deals” where Trump charges supporters more than the website price. He mocks the “Trump time” watch grift and the endless begging emails: Do you love me? Take the poll. Send money.
Colbert, meanwhile, tears into Trump’s obsession with power, his fantasy that comedians should be prosecuted for “illegal donations,” and his pathetic attempts to turn late-night jokes into criminal offenses. He wears a fake mustache, laughs at being on Trump’s enemies list, and says, “There’s no guarantee I’ll be arrested, but it’s an honor just to be nominated.”
These two aren’t rivals. They’re allies.
They share group chats with other late-night hosts. They’ve joined forces on the Strikeforce 5 podcast to support staff during strikes. They defend each other publicly. When Colbert was canceled, Kimmel posted, “Love you, Stephen,” and told CBS exactly where they could shove that settlement.
Trump wanted to break them apart.
Instead, he forged the strongest alliance late night has ever seen — and handed his loudest critics a bigger audience, a clearer mission, and a permanent role in documenting his downfall… one punchline at a time.
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