BS BULLETIN:
- Jelly Roll unloaded on President Trump while guest-hosting Jimmy Kimmel Live! Monday night.
- The country star mocked Trump’s weight, flag-waving and approval ratings.
- Quite a turn for the man who once defended respecting the president and insisted: “I’m not political!”
Well, that escalated quickly.
Country superstar Jelly Roll stepped behind Jimmy Kimmel’s desk Monday night and apparently decided the price of admission to late-night television was taking a few swings at Donald Trump.
The singer, whose real name is Jason DeFord, was filling in for Kimmel when his opening monologue turned into a sustained Trump roast — surprising viewers who remembered Jelly Roll’s very different comments after meeting Trump at UFC 309 in 2024.
He started with Trump’s appearance at Sunday’s Freedom 250 Grand Prix in Washington, D.C., mocking the president’s flag-waving before declaring, “What a shit job!” and asking how someone could mess up waving a flag. He then joked that Trump enjoyed the race because “normally he only likes his own race.”
Then came the weight jokes.
Jelly Roll, who has famously undergone a dramatic weight-loss transformation, told the audience he had lost roughly 300 pounds.
“That means I’ve lost an entire Donald Trump,” he joked, before adding a crack about the president’s approval ratings.
And then he went considerably lower.
Addressing Trump directly, Jelly Roll said, “from one fat pig to another,” physical fitness was important — before delivering an NSFW punchline about one of the benefits of losing weight.
He offered the president some very personal encouragement: “Trust me, you’ll be happy to see your penis again.” Then he took the joke even further, telling the audience that when he finally saw his own again after losing the weight, he was “surprised at how cute it was” — and cracked that it looked like “a little Labubu doll.” The audience roared, but for fans who remembered Jelly Roll preaching respect for the presidency not all that long ago, this was quite the transformation — and we’re not talking about the 300 pounds.
The studio audience laughed. Plenty of people watching elsewhere were scratching their heads.
Because this is the same Jelly Roll who sounded markedly different after he was criticized for enthusiastically greeting Trump at UFC 309 in Madison Square Garden shortly after the 2024 election.
At the time, Jelly Roll dismissed the backlash.
“There’s not a chance in hell that I’m not going to meet the president-elect,” he said, explaining that he would have done the same if Joe Biden invited him to meet. “I’m not political!”
More strikingly, Jelly Roll said his parents had taught him to respect the president because it was “the hardest job in the world.”
“Respect whoever has it,” he said.
And his verdict after meeting Trump? “Meeting President Trump was cool. Ultimately, I don’t really care [about] any blowback I get about it. The truth is: It was really cool to meet the president.”
Apparently “respect whoever has it” has an expiration date — or perhaps a guest-hosting gig at Jimmy Kimmel Live! comes with different instructions.
To be fair, Jelly Roll has always insisted he isn’t particularly political, and roasting politicians is certainly nothing new for late-night television. But when a guy goes from defending respect for the presidency to calling the sitting president a “fat pig” on national television, people are going to notice the tonal adjustment.
Especially when the desk says Jimmy Kimmel on it.
So unfortunate Jelly Roll decided to use his gig on Kimmel to attack President Trump. I’ve been a fan of his for years. While he touts his own weight loss, and calls out Trump for calling others fat, he refers to him as a fat pig. One fan lost.🤨 pic.twitter.com/4OZOAcVELz
— Plein Crazy (@PleinCrazy) August 25, 2026
MY QUICK TAKE
Jelly Roll once said he didn’t know enough about politics to pretend he knew what politicians stood for and that he was raised to respect the president.
Then he got to Hollywood and apparently somebody handed him the late-night starter kit.
Step one: Trump joke.
Step two: Trump fat joke.
Step three: Wait for applause.
Congratulations. You’re officially qualified for late night.
DBS WIRE SOURCES:
- Breitbart — Jelly Roll unleashes penis jokes, fat jokes on Trump in ‘Jimmy Kimmel Live!’ hosting return
- TV Insider — Jelly Roll shocks with Trump comments as he hosts ‘Jimmy Kimmel Live!’
- TheWrap — Jelly Roll stuns ‘Jimmy Kimmel Live’ audience with multiple jabs at Trump
- Fox News — Jelly Roll defends Donald Trump encounter, stresses importance of respecting the president
- New York Post — Jelly Roll defends Trump encounter at UFC event












