Country singer Jason “Jelly Roll” DeFord, 41, has been open about his weight-loss journey. He dropped nearly 300 pounds after tipping the scales at over 540 pounds.
The Grammy Award winner sported his slimmed-down look on “Jimmy Kimmel Live!” this week. He began his stint at the helm by roasting President Donald Trump, who has put on more than a few pounds recently.
The “Need a Favor” hitmaker used his opening monologue to offer the heavyset POTUS some much-needed advice.
Trump’s nemesis, Jimmy Kimmel, might be on vacation, but his show’s temporary hosts have gladly taken on the mission of lambasting Trump on a nightly basis.
The television personality, who has been feuding with the president for years, tapped celebrities such as actor Anthony Anderson and comedian Rosie O’Donnell to fill in for him throughout the summer.
After mocking Trump’s weird flag-waving movements at Sunday’s Freedom 250 Grand Prix in Washington, Jelly Roll resumed his comedic onslaught.
“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,” Jelly Roll told the audience on Aug. 24.
The Tennessee native said, “Sadly, those are the only laps Trump’s been doing lately.” His joke garnered both laughs and groans from the live studio crowd.
Jelly Roll then focused on reports that suggest Trump gained only 14 pounds between 2025 and his 2026 medical exam. The president’s physician listed him at 6 feet 3, 238 pounds in May.
“It’s crazy. Think about this, y’all. In the last few years, I’ve lost 300 pounds… That means I’ve lost an entire Donald Trump,” he quipped.
Jelly Roll: A lot of doctors are worried about Trump's weight. He's now tipping the scales at 240. I've lost 300 pounds—I've lost an entire Donald Trump. And based on his approval ratings, it seems like most of the country wants to do the same thing. pic.twitter.com/1k3xA29TVB
— FactPost (@factpostnews) August 25, 2026
Jelly Roll turned sarcastic, saying, “We shouldn’t be making fun of the president for his weight.” He added that Trump “would never do that to other people.”
The show backed up the joke with footage of Trump mocking political rivals.
In the clip, the former reality television star insults Montana Democratic Sen. Jon Tester for having “the biggest stomach” he has ever seen.
Another flashback shows Trump calling Democratic Illinois Gov. JB Pritzker a “fat slob” played too. The montage also featured the outwardly obese grandfather repeatedly saying “fat pig.”
Jelly Roll’s takedown of the MAGA chief picked up again. Standing with his hands crossed in front of him, he emphasized, “Well, if that ain’t the pot calling the kettle fat.”
The deadpan Southerner accented his roasting session of Trump by issuing a low blow against the notoriously thin-skinned commander in chief.
“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,” Jelly Roll suggested.
Jelly Roll’s NFSW jab at Trump has not garnered a response from the president, as of this writing.
But people on social media predict that the flagrant keyboard warrior will likely have a vicious comeback in the near future.
“Donny is about to be mad,” one person wrote in the comment section of the “Jimmy Kimmel Live!” Instagram page. One reply read, “Big mad!!!”
Another individual wrote, “Whaaaaaat, I was not expecting this from Jelly. What a nice surprise.”
Not all the responses praised the “Beautifully Broken” album creator. Some fans were disappointed that O’Donnell’s turn as guest host had ended.
An entertained Instagram user posted, “What the hell happened to Rosie O’Donnell? I’m just kidding, this is great.” However, that supporter’s feelings were not universal.
Another exclaimed, “Waaaah!? What a downer after Rosie. We don’t get it.”
Jelly Roll was also called out for his past friendly association with Trump. An annoyed Instagram poster commented, “Nahhhhh, don’t care how you paint it… not falling for it. Go lick their boots back where you came from.”
Back in November 2024, cameras captured Jelly Roll greeting Trump with a wide smile at the UFC 309 event in New York City.
Following the intense backlash over his joyful encounter with the then-presidential-elect, Jelly Roll defended his cordial experience with the polarizing conservative firebrand.
“Y’all couldn’t feel what we were feeling,” he told the New York Post in reaction to complaints about the “goofy smile” on his face while meeting Trump. “Like that room was palpitating.”
The part-time WWE wrestler said, “There’s not a chance in hell I’m not going to meet the president-elect.”
Nevertheless, his attempt to distance himself from politics two years later raised more eyebrows.
Jelly Roll’s huge night at the 68th Annual Grammy Awards in February was partially overshadowed by his backstage statements on American politics.
When asked by a reporter to share his thoughts on the state of the country under Trump’s leadership, Jelly Roll leaned into his Southern heritage to shield him from speaking on current affairs of state.
“I’m glad somebody asked, because I love talking about this stuff, and people care to hear my opinion, but so I can tell you that people shouldn’t care to hear my opinion,” Jelly Roll responded.
The father of two said he didn’t have access to news coverage. He expounded, “I’m a dumb redneck. I haven’t watched enough. I didn’t have a phone for 18 months. … I’m so disconnected from what’s happening.”
