Jelly Roll Roasts Trump's Flag Waving and Weight on Kimmel

During his recent guest hosting stint on Jimmy Kimmel Live!, country singer Jelly Roll directed several pointed jokes at former President Donald Trump. In his opening monologue on Monday night, Jelly Roll began by referencing the IndyCar race in D.C., humorously criticizing Trump's grasp of flag-waving protocol. He quipped that Trump's 'lap of honor' sounded like a strip club loyalty program, implying a lack of actual political engagement.

Further into his monologue, Jelly Roll addressed reports about Trump's physical health, referencing a 14-pound weight gain. He contrasted this with his own 300-pound weight loss, stating he had 'lost an entire Donald Trump.' Jelly Roll also presented a montage of Trump making disparaging remarks about others' weight and appearance, before concluding that 'from one fat pig to another,' physical fitness is crucial.

This appearance on August 26, 2026, was Jelly Roll's second time guest hosting the show, with his first being in July 2025. The artist has previously maintained an apolitical public stance, describing himself as a 'dumb redneck' when asked about his political views.