Jelly Roll Urges Trump to Lose 14 Pounds on Jimmy Kimmel Live

Q: Why did it take a late-night TV gig for Jelly Roll to finally wear a suit, skipping formal attire at the Grammys and court?

It appears to have been a joke about his long-running indifference to formal dress, not a sign that the TV job somehow required a personal breakthrough. In his “Jimmy Kimmel Live” monologue, Jelly Roll said it was the first time he had ever worn “a suit and a tie,” then laughed that he had skipped one for the Grammys, court and even his father’s funeral. The available reporting gives no deeper practical reason beyond his own comic framing: he has built a public image around being informal, self-deprecating and unconcerned with traditional celebrity polish. The late-night hosting role simply gave him a fresh setup for that joke. Appearing behind a network desk in a classic host look — suit and tie — let him underline how unusual formalwear is for him and turn it into an easy punchline about his past. In other words, the gig did not necessarily “make” him do it so much as provide the most visible and amusing moment to acknowledge that he almost never dresses that way. So the best answer is that Jelly Roll wore the suit because the late-night host setting called for the classic TV-host costume, and he used that contrast with his usual style as part of his monologue humor. No evidence suggests a more serious explanation than that.

Q: Amidst a shocking divorce, a new baby, and stepping back from touring, what unexpected path is this country star carving out next?

Jelly Roll is moving into late-night television, taking on a guest-host role on **“Jimmy Kimmel Live!”** as an unexpected next step. The move comes during a turbulent personal stretch. Reports say he filed for divorce from Bunnie Xo after about a decade of marriage, though both have said they remain close and committed to co-parenting, and they have continued discussing plans to grow their family. At the same time, he has scaled back touring after finishing dates with Post Malone, saying he needed time to recover and heal. Against that backdrop, guest-hosting marks a notable career expansion beyond music. Jelly Roll had already filled in on **“Jimmy Kimmel Live!”** last summer, and ABC brought him back as part of its new rotation of summer hosts. His monologue leaned on his weight-loss journey, his self-deprecating humor, and his growing comfort on camera, signaling that he is becoming more than a recording and touring artist. The broader picture is that Jelly Roll appears to be carving out a second lane in entertainment: **television personality and host**. With fewer tour dates, a major public profile, and proven late-night appeal, the guest-host stint suggests he is testing a more permanent presence in TV while navigating major changes in his personal life.

3 articles · Updated · Rolling Stone · Aug 25

Jelly Roll used his Jimmy Kimmel Live guest-host monologue to tell Donald Trump to slim down, citing reports that the president gained 14 pounds and now weighs nearly 240.
The attack centered on what Jelly Roll cast as hypocrisy: he said Trump mocks other people’s size, then the show rolled clips of the president ridiculing others’ weight and appearance.
Drawing on his own 300-pound weight loss, Jelly Roll joked he had “lost an entire Donald Trump” and said much of the country seemed to want the same, nodding to Trump’s approval rating.
The appearance fits Jelly Roll’s recent shift toward speaking more openly in public, after saying earlier this year he had long felt disconnected from politics.