Jelly Roll used his four night guest hosting run on Jimmy Kimmel Live to criticize Donald Trump on August 25, 2026. The country singer mocked Trump’s comments about people’s bodies, referenced reports about the president’s weight, and delivered a very NSFW punchline about physical fitness. Jelly Roll opened by joking about wearing a suit and tie for the first time, saying he skipped the look at the Grammys, court, and his father’s funeral. He then turned to Trump’s appearance at an IndyCar race in Washington, D.C., comparing the president’s motorcade “lap of honor” to a strip club loyalty program. Jelly Roll Came With Receipts Jelly Roll cited Washington Post reporting that doctors had raised concerns about Trump’s weight and that Trump gained 14 pounds after his previous physical, bringing him close to 240 pounds. The singer, who said he has lost 300 pounds in recent years, cracked that he had effectively “lost an entire Donald Trump” before reminding viewers that Trump has publicly mocked other people’s size and appearance. Jelly Roll then framed his punchline as advice from “one fat pig to another,” telling Trump that physical fitness matters and claiming the president would be happier with a healthier body. The joke landed as classic late night political roasting, but Jelly Roll’s broader point was sharper: public figures who weaponize appearance should expect the same energy back. Jelly Roll’s political commentary follows his Best Contemporary Country Album win for Beautifully Broken at the 2026 Grammys. In the press room, Jelly Roll said he had once felt disconnected from politics because of his chaotic childhood and time in jail, but now planned to speak about the country “in the most loud and clear way.”