During his summer vacation, Jimmy Kimmel has invited celebrity guest hosts to fill in for him on Jimmy Kimmel Live! Much to President Donald Trump’s dismay, Rosie O’Donnell hosted the show last week. Given that Trump and O’Donnell have been feuding for years now, no one was surprised that she used the gig to mock the president.
What people were not expecting, however, was for Jelly Roll to do the same thing. Jelly Roll’s guest-hosting gig started on August 24. That night, he surprised viewers by making jokes about Trump. Some of his fans were outraged and even threatened to stop listening to his music.
Jelly Roll’s previous comments (or lack thereof) about politics had both fans and critics convinced he was a Trump supporter.
🚨 JELLY ROLL EXPOSED AS A MASSIVE FRAUD
— Eric Daugherty (@EricLDaugh) August 26, 2026
He’s now attacking Trump, yet was previously ECSTATIC when he walked up to President Trump — acting like his biggest fan
Hollywood changes people for the worst! pic.twitter.com/nCxYiUuUUz
To be fair, Jelly Roll never claimed to support Trump. But people had their reasons for suspecting that. This year, at the Grammys, Jelly Roll declined to comment on politics. When asked about his beliefs, he acted like they should be irrelevant to people; no one should “care to hear (my) opinion,” he said.
He also called himself “a dumb redneck” and said he has “become so disconnected from what’s happening.”
But the fact that he wouldn’t actually speak out against Trump made a lot of people think that he supported him. They thought his apparent apathy spoke volumes.
At the time, Jelly Roll vowed to make his views known at a later date. “Everybody’s going to hear exactly what I have to say about it in the most loud and clear way I’ve ever spoken in my life,” he promised at the time. “So I look forward to it.”
He also met Trump in 2024.
😬 Jelly Roll roasts Trump's weight and says he can't see his penis.
— TMZ (@TMZ) August 25, 2026
Credit: ABC pic.twitter.com/lP2hC8TTts
He was spotted interacting with Trump at the UFC 309 event in November of that year. Again, people took the friendly interaction to mean that he actually liked Trump. He later addressed the backlash, claiming he just thought meeting the president seemed “cool.”
“Dude, there’s not a chance in hell that I’m not going to meet the president-elect,” he said at the time. “I don’t care. If I got a call to meet Joe Biden, I would have stopped at any point and (met) him. That’s the active president. I don’t care about what he thinks or I think about policies.”
And similar to what he said at the Grammys, he emphasized that he’s truly “not political” and is not “hiding behind” that or using it as an excuse. “Meeting President Trump was cool,” he said. “Ultimately, I don’t really care (about) any blowback I get about it. The truth is: it was really cool to meet the president.”
While he’s not the only person who has made an argument like this one, critics didn’t find it very convincing. Most critics of Trump would presumably not want to meet him and would not think seeing him at an event was “cool.”
So, the jokes he told on Kimmel’s show surprised people.
Perhaps in a good way or in a bad way, depending on who you ask. On Monday’s episode, Jelly Roll joked about Trump’s weight — and his approval ratings. He mentioned his own weight loss journey, noting that he’s lost more than 300 pounds.
“That means I’ve lost an entire Donald Trump,” he said. “And let’s be honest, based on his approval rating, it seems like most of the country wants to do the same thing.” Oof.
His Trump jokes sparked so much backlash that he actually addressed it during Tuesday’s episode. He actually felt compelled to explain the concept of late-night comedy to people: “It’s because I’m hosting a d— late-night show,” Jelly Roll explained. “That’s where you talk about the news, and you make jokes.”
He also seemed surprised by the outrage.
From his perspective, the fact that he made a few jokes about Trump is not exactly the most unusual or controversial thing about him. “I have to say, as a former felon, drug dealer who has lost 300 pounds, has tattoos all over his face, and won three Grammys, this is the weirdest thing I’ve ever done to stun people,” he said.
Again, he took a self-deprecating approach. “Some folks online were upset that I didn’t treat the president with reverence and dignity,” he said. “But I want to remind y’all that I go by the name Jelly Roll. I don’t even treat myself with reverence and dignity.”
Some fans have threatened to boycott his music because of his jokes, and he had a message for them as well: “I just want to say with conviction: go right ahead, ’cause I’m going to keep speaking my truth, or my name isn’t Post Malone.”
And he, too, seemed surprised that his Trump jokes seemingly bothered people more than the jokes O’Donnell made. “Who would’ve guessed I’d get in more trouble with the president than Rosie O’Donnell?” he added.
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