Jelly Roll stepped in as guest host of Jimmy Kimmel Live this week and used his opening monologue to go after Donald Trump’s weight and the president’s habit of mocking people for how they look. The country star said it was the first time he had ever worn a suit and tie, then turned the spotlight on himself and Trump in the same breath.
“I didn’t wear one to the Grammys,” he said. “I didn’t wear one to court. I didn’t wear one to my father’s funeral. But I look alright, don’t I?”
The appearance matters because Jelly Roll is not just filling time on a late-night desk. He is using it to say something pointed in front of a national audience, and he is doing it while leaning into the image that made the moment land: a performer who said he has lost 300 pounds over the past few years now standing in a suit and tie for the first time. “That means I’ve lost an entire Donald Trump,” he said.
The monologue came during a four-night run on Jimmy Kimmel Live, a stretch that keeps Jelly Roll in the spotlight while the show’s regular host is away. Last year, he first stepped in as guest host, and this week he brought the same loose, confrontational style to a subject that has followed him for months: how to talk about body image after his own weight loss without softening the insult when he aimed it at someone else.
Jelly Roll framed Trump’s weekend trip to Washington, D.C., around the IndyCar race as “the main event in America this weekend,” then joked that Trump “only likes his own race.” He said Trump drove around the track in his motorcade doing the “lap of honor,” a phrase he said sounded like a loyalty program at a strip club. He added that Trump had been doing only those laps lately, said Trump had gained 14 pounds after his last physical, and said he was now “tipping the scales of almost 240.”
That is where the joke turns sharp. Jelly Roll used the same stage to criticize Trump for making fun of fat people while using the kind of language he was condemning. He said the late-night show played clips of Trump mocking people based on size and appearance, then told him, “Well Mr. President, from one fat pig to another, take it from me that physical fitness is very important.” He followed that with another line that pushed the monologue even further: “And trust me, you’ll be happy to see your penis again.”
The contradiction is part of what gave the segment its charge. Jelly Roll presented himself as someone who knows the subject from the inside — he said he had lost 300 pounds, and he has also said he planned to speak out “in the most loud and clear way” at the Grammys earlier this year. On Sunday night, he won Best Contemporary Country Album for Beautifully Broken at the Grammy Awards, which added another layer to a week that has already put him in front of a huge audience twice over.
He has also talked before about how far removed he once was from public life. In an interview with Rolling Stone, he said he became so disconnected from what was happening that he did not even know politics were real until his mid-twenties in jail. He said he grew up in a house of “insane pandemonium” and came from a drug addict household. That history helps explain why his latest late-night turn felt less like a novelty booking and more like a man using the mic exactly as he wants.
Jelly Roll’s run on Jimmy Kimmel Live continues for four nights, and last night’s guests included Jay Shetty and Glen Powell. He also revealed he has a small role in Glen Powell’s forthcoming film The Comeback King. But the bigger draw this week is already clear: Jelly Roll is treating the guest-host seat as a place to say the quiet part out loud, and he is doing it with Trump still in his sights.
