The country-rap star, whose real name is Jason DeFord, filled in for Kimmel during the host’s summer hiatus. On Monday, Aug. 24, he opened with material about his own 300-pound weight loss and Trump’s reported weight gain, saying he had “lost an entire Donald Trump” and that “based on his approval ratings, it seems like most of the country wants to do the same thing.”
Additional bits that week targeted Trump’s appearance at an IndyCar event and a trade dispute with Canada. Clips of Trump insulting others’ weight were played for contrast.
The jokes surprised parts of his audience. Jelly Roll had previously avoided partisan talk, once calling himself a “dumb redneck” disconnected from politics when asked about ICE at the 2026 Grammys.
He had also shaken Trump’s hand at a 2024 UFC event and later defended that gesture as respect for the office, not an endorsement. Some conservative commentators and fans accused him of turning on Trump or of being coached by Kimmel’s writers.
At least one Florida official, Jimmy Patronis, publicly said he was unwelcome in the Panhandle.
Jelly Roll addressed the reaction mid-week without walking the jokes back. He said any U.S. president should be able to handle a few jokes, noted that he was hosting a late-night comedy show, and told fans who threatened to stop listening, “Go right ahead.” He joked that people were stunned a face-tattooed former felon had opinions at all.
On Thursday, August 27, his final night, he delivered a lengthy, at times tearful monologue. He rejected the idea that writers had forced the Trump material: “Do you think I would take orders from some sweaty little dork named Josh? No, I was just telling it like it is.” He observed that before the week “everybody thought I was MAGA, and now they think I’m some sort of liberal snowflake,” then described himself as “pretty down the middle” while leaning left on some issues.
He is a Christian, a hunter, and a farmer, he said. A handshake with a president is not an endorsement, a conversation is not allegiance, and “a joke ain’t a political stance.” He said he would always shake the hand of a sitting president out of respect for his late father, a Marine veteran.
He also expressed regret about the Grammys. He said he had a microphone that night and “didn’t use it the right way,” fearing any comment would be read as a political statement. “Ironically, by trying so hard not to make a political statement, I became one.”
He pledged to defend “human dignity” and argued that compassion and mercy are not owned by either party. In a follow-up social-media post he repeated that a handshake is not an endorsement and a joke is not a political stance, adding that he would try harder to love his neighbor.
As of August 29, 2026, the episode illustrated how quickly a popular artist with a broad, working-class fan base can be pulled into partisan combat. Jelly Roll framed his week as consistency with his own redemption story and with free speech, not a conversion.
Whether that lands with fans who felt betrayed, or with those who wanted a stronger political stand earlier, remains an open question.
