Jelly Roll took multiple shots at President Donald Trump while filling in as guest host on “Jimmy Kimmel Live” Monday, to the surprise of many of the country musician’s fans.
The singer, who is best known for “Save Me,” “Son of a Sinner” and “I Am Not Okay,” first made fun of how the president waved the green flag, getting the Freedom 250 Grand Prix race underway in Washington, D.C., on Sunday, TheWrap reported.
“Let’s talk about the main event of America this weekend. It was the big IndyCar race hosted by the president,” Jelly Roll said in the show’s opening monologue. “The cars drove through the streets of D.C., and there’s Donald Trump, who apparently has never held a flag before.”
“What a s*** job! How do you f*** up waving a flag?” he added.
Jelly likely did not write any of his own jokes, but the Kimmel show people who probably did, of course, had to trot out that favorite Democrat saw: Trump’s a racist.
The artist said, “The president seemed to enjoy the IndyCar race, which was a real switch-up for him because normally he only likes his own race,” to the delight of the audience.
WARNING: The following video clip contains vulgar language that some may find offensive.
[embedded content]
He continued: “Trump also drove around the track in his motorcade doing what they call the ‘lap of honor.’ Which sounds like a loyalty program at a strip club: 5 percent cash back in the champagne room for all Lap of Honor members.”
Jelly, who has had his own challenges in packing on the pounds over the years, then shifted into making fun of Trump’s weight.
“Sadly, those are the only laps Trump’s been doing lately. According to The Washington Post, a lot of doctors are worried about the president’s weight. After his last physical, we found out Trump gained 14 pounds, which means he’s now tipping the scales at almost 240,” he said.
“It’s crazy. Think about this, y’all. In the last few years, I’ve lost 300 lb. That means I’ve lost an entire Donald Trump,” Jelly pointed out. “And let’s be honest, based on his approval ratings, it seems like most of the country wants to do the same thing.”
He then showed past clips of Trump calling out others for being overweight, like New Jersey Gov. Chris Christie.
“Well, if that ain’t the pot calling the kettle fat,” Jelly Roll said. “Well, Mr. President, from one fat pig to another, take it from me that physical fitness is very important. And trust me, you’ll be happy to see your penis again.”
Pretty low-class stuff, and fans were not liking it.
One wrote in the comments on YouTube, “Wait, hold up. Isn’t Jelly Roll MAGA? I’m very confused right now.”
“Um wow I was not expecting him to trash talk trump,” someone else added.
Another posted on X, “I’ve been on this Rollercoaster with you for about 25 years. I worried when you went mainstream that you would forget where you come from. I see it didn’t take long for that to happen… smh. From a disappointed long time fan.”
@JellyRoll615 I’ve been on this Rollercoaster with you for about 25 years. I worried when you went mainstream that you would forget where you come from. I see it didn’t take long for that to happen… smh. From a disappointed long time fan. https://t.co/9vqxclpdvB
— Amanda (@Gigi54374) August 25, 2026
Still another said, “Jelly Roll should remember something: a massive part of country and Southern music’s audience is conservative. 🇺🇸 You’re free to criticize President Trump or disagree with his politics—but when you start insulting the people your audience includes, you risk alienating the very fans who buy your music, attend your concerts, and support your career.”
🚨🔥 JELLY ROLL MAY HAVE JUST MADE A HUGE MISTAKE!
Jelly Roll should remember something: a massive part of country and Southern music’s audience is conservative. 🇺🇸
You’re free to criticize President Trump or disagree with his politics—but when you start insulting the people… pic.twitter.com/wf72s5QAip
— Reverend Jordan Wells (@WellsJorda89710) August 25, 2026
Kimmel’s joke writers are caught in a left-coast bubble, and Jelly Roll is apparently too clueless to realize he should not be alienating Trump supporters, who no doubt make up a large swath of his fan base.
Advertise with The Western Journal and reach millions of highly engaged readers, while supporting our work. Advertise Today.
