Jelly Roast: Jelly Roll jokes about Trump’s weight, flag mishap on ‘Kimmel’

Country music star Jelly Roll spent part of his Monday night guest-hosting stint on “Jimmy Kimmel Live!” mocking President Trump’s flag-waving at a Washington, D.C., IndyCar race and his reported weight gain, a monologue that left some of his fans confused about where the singer actually stands politically.

The Grammy winner, filling in for host Jimmy Kimmel for the second year in a row while the show is on summer hiatus, opened by walking the studio audience through “the main event of America this weekend” — Sunday’s Freedom 250 Grand Prix in Washington, where Mr. Trump took a ceremonial lap in his motorcade. “The cars drove through the streets of D.C., and there’s Donald Trump who apparently has never held a flag before,” Jelly Roll said, before adding, “What a s—- job! How do you f—- up waving a flag?”

He went on to compare Mr. Trump’s motorcade lap to “a loyalty program at a strip club,” then pivoted to the president’s weight, citing a Sunday Washington Post report that found Mr. Trump had gained 14 pounds between his two most recent White House physicals. “In the last few years, I’ve lost 300 pounds. That means I’ve lost an entire Donald Trump,” Jelly Roll cracked, before running a montage of the president mocking other people’s weight and appearance over the years.

The bit caught some viewers off guard, with commenters cited by TheWrap questioning whether Jelly Roll was a Trump supporter — one asked, “Isn’t Jelly Roll MAGA?” while another admitted being confused. The singer has previously said he has no party affiliation, telling members of Congress in 2024 testimony on the fentanyl crisis that he stays out of politics and, because of his criminal record, isn’t even eligible to vote.

A White House spokesman did not immediately comment on the monologue.