Jelly Roll Doubles Down on Trump Jokes After Jesse Watters' TDS Attack

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 · TV Insider · Aug 27

On Wednesday's Jimmy Kimmel Live!, Jelly Roll answered Jesse Watters' "Trump Derangement Syndrome" jab by mocking the Fox host and pressing ahead with jokes about Donald Trump.
His monologue targeted Trump's trade fight with Canada, saying it could raise prices for products including whiskey, smartphones and toilet paper, then turned again to the president's weight and fitness.
Jelly Roll said the backlash centered less on his broader Trump material than on calling the president overweight, and he framed the shots as standard late-night comedy while guest-hosting Kimmel's show.
The exchange builds on jokes earlier this week in which Jelly Roll contrasted Trump's reported 14-pound weight gain with his own 300-pound weight loss, turning a one-off monologue into a broader Fox-versus-late-night spat.