If you thought late-night TV was in trouble this year – with Colbert’s Late Show axed by CBS in July and Kimmel yanked off ABC for a week in September over that infamous Charlie Kirk bit – think again. Last Tuesday, September 30, 2025, Jimmy Kimmel and Stephen Colbert pulled off the roast of the century: a simultaneous crossover where they invaded each other’s shows, live from New York, and turned Donald Trump into their shared piñata. The result? A barrage of zingers so sharp they could slice through Mar-a-Lago’s gold-plated doors, covering everything from government shutdowns to Epstein file signings, Trump’s “snowflake” meltdowns, and yes, even his spray-tan empire. By midnight, Trump was rage-tweeting from the White House, calling them “two total losers” with “horrible ratings.” Spoiler: the only thing with horrible ratings that night was Trump’s approval poll.
It started innocently enough – or as innocent as these two get when plotting against a president. Kimmel, in Brooklyn for his “Brooklyn Week” special, welcomed Colbert to Jimmy Kimmel Live! with a bear hug and a cocktail. “I am so honored to be here with my fellow no-talent, late-night loser,” Kimmel quipped, winking at Trump’s favorite slur for them both. The crowd – a mix of New Yorkers who’d lined up at 4 a.m. – erupted into chants of “Lock him up!” as Colbert raised his glass: “To surviving cancellation… and making sure Don doesn’t.”
But this wasn’t just banter; it was a full-on assault, timed perfectly amid the October 1 government shutdown – the first since 2019, courtesy of Trump’s MAGA holdouts in Congress. Colbert, ever the edgelord, kicked off with a supercut of Trump signing executive orders “off-camera” like a guilty kid hiding report cards. “He signed the Epstein files bill after issuing a ‘photo lid’ – that’s White House speak for ‘I’m hiding from the press.’ Trump avoiding cameras? That’s like the Pillsbury Doughboy dodging a bakery. And get this: he’ll sign anything on camera – sneakers, walls, lady parts – but not this? Suspicious much?”
Kimmel piled on, flashing a chyron reading “Moments Away from Shutdown: Thanks, Don!” “We’re about to furlough 800,000 federal workers because Trump can’t stop golfing long enough to negotiate. It’s like if your uncle ruined Thanksgiving by demanding everyone salute his bald eagle tattoo.” The duo toasted to “driving the president nuts,” with Colbert adding, “We thought it’d be fun to swap shows – you know, like how Trump swaps mistresses, but with better hair.”
Two hours later, the roles reversed at the Ed Sullivan Theater. Kimmel strolled onto The Late Show to a standing ovation and “Jimmy! Jimmy!” chants that drowned out the band. Trump-watchers knew this was war: just days earlier, on November 20, Kimmel had solo-roasted Trump over the Epstein signing, calling him “the Suntan Kid” who “flips out every five weeks wanting me fired. Talk about a snowflake!” Now, with Colbert’s crowd roaring, Kimmel doubled down: “I’ll go when you go, Don. We’ll ride off into the sunset like Butch Cassidy and the guy who can’t keep his racism straight.”
The roasts spanned the year’s lowlights like a greatest-hits album from hell. Colbert dusted off Trump’s first 100 days (back in April), mocking a Fox News poll showing majority disapproval: “Even Fox says you’re tanking, Don. And when Stephen Miller says ‘fire the pollster,’ it’s like Trump University giving refunds – pure fantasy.” Kimmel, not one to be outdone, replayed Trump’s Truth Social tirade from after Kimmel’s suspension: “‘Jimmy and Seth, two total losers on Fake News NBC.’ Don, if we’re losers, why are your rallies half-empty? Oh right, because people finally read the fine print on those red hats: ‘Warning: May cause spontaneous combustion.'”
They didn’t spare the scandals. On the Epstein files – signed begrudgingly off-camera amid bipartisan pressure – Colbert quipped, “Trump’s so desperate to bury it, he’s probably gluing the docs under his toupee. Remember that wind video? His hair filed for asylum before the files did.” Kimmel followed with a deepfake of Trump in a sombrero yelling at Hakeem Jeffries, tying it to Trump’s “can’t even keep his racism straight” gaffes. And the shutdown? “Trump’s celebrating Americans losing jobs like it’s his third divorce,” Kimmel said. “Shocking for a president who’s basically a walking ‘You’re Fired’ sign.”
The audience? Electric. Phones lit up like fireflies as clips went viral – 23 million views on TikTok by 11 p.m., #LateNightRevenge topping trends. One viewer tweeted: “Kimmel and Colbert just turned Trump into a human stress ball. Popcorn emoji x100.” Even Seth Meyers jumped in from NBC, posting a photo of himself in a red hat: “Solidarity, brothers. Don, your move – cancel us all?”
Trump’s response? A 2 a.m. Truth Social screed that read like a fever dream: “Why does ABC keep the no-talent Kimmel? And CBS with that fat fraud Colbert? Their ratings are TERRIBLE! Do it NBC!!! President DJT.” By morning, it had 4.2 million likes from MAGA diehards, but the replies were a bloodbath: “Ratings terrible? Kimmel beat your election watch party by 3 mil viewers, Don.” Karoline Leavitt, Trump’s press secretary, went on Fox to “explode” about the “disrespect,” but it only fueled more memes – her face Photoshopped onto a melting snowflake.
This wasn’t isolated; it’s the culmination of a brutal 2025. Colbert’s July cancellation came after he slammed CBS for a $16 million Trump settlement – “martyr status achieved,” he joked. Kimmel’s September suspension? Blamed on FCC threats post his Kirk monologue, where he quipped about the commentator’s death: “Charlie who? Oh, the guy Trump wishes was his VP.” Disney caved briefly, but ratings soared 40% upon return, proving America loves a fighter.
The crossover? A masterstroke of unity. As Kimmel told People, “We swapped to show late-night’s not dead – it’s just got better aim.” Colbert echoed on The Economic Times: “Shocking that a president celebrates job losses. But hey, Don – we’re still here, and you’re still orange.”
By week’s end, petitions hit 120,000 signatures demanding “Protect Late Night from Trump.” Merch flew: “No-Talent Loser” tees outsold MAGA hats on Etsy. And Trump? Radio silent since, probably plotting his next “fire them all” rant.
Jimmy and Stephen didn’t just roast Trump – they barbecued him, served him with a side of schadenfreude, and watched the fireworks light up the resistance. In a year of shutdowns and scandals, this was the reminder: comedy’s the ultimate check on power. And Trump? He really, really doesn’t like it. Tune in tonight – the tag-team’s just warming up.
