Jimmy Kimmel Subtly Backs MAGA's Most-Hated Guest Host

Jimmy Kimmel has Jelly Roll's back after MAGA disowned the rapper for dissing Donald Trump. Jelly Roll, whose real name is Jason Bradley DeFord, filled in for Kimmel as one of the host's rotating guest stars in August. And during his week-long run of shows, he took several shots at Trump, including about the president's weight. The 41-year-old country singer subsequently became a MAGA nemesis, with fans publicly denouncing him on social media. On Sunday, he was dropped from a Mar-a-Lago event hosted by the conservative group Blue Lives Matter, which declared that he was 'FIRED.' Amid mounting backlash, Kimmel appears to be standing by the Grammy-winning artist. The ABC host posted a summer-themed photo dump on Instagram, including a grinning selfie with Jelly Roll, who joined him for a fishing trip at the host's Montana ranch. Instagram/screengrab Previously considered apolitical, Jelly Roll took a significant step during his stint on Jimmy Kimmel Live! In February, the singer won his first Grammy Award–eventually taking home three in one night–and was asked about his political stance. He admitted to reporters, 'I didn't even know politics were f---ing real until I was in my mid-20s in jail.' He consciously decided to course-correct while hosting Kimmel, as he explained eloquently on the show. Jelly Roll ended his week with a tearful monologue revealing exactly why he took potshots at the president. 'A lot of people seem to think these Jimmy Kimmel writers have secretly been pulling the strings and forcing this good old country boy to poke fun at our commander-in-chief,' said the 'Need a Favor' singer. 'It is funny that before this week, everybody thought I was MAGA, and now they think I'm some sort of liberal snowflake,' he continued. 'I guess I'm just not used to people projecting their beliefs onto me.' He explained that he 'fumbled' his words at the Grammys when asked to take a political stance amid widespread ICE violence. Jelly Roll admitted, 'That night at the Grammys, I had an opportunity to speak up for people who were scared, hurting, and felt like nobody was speaking for them. I had a microphone, and I didn't use it the right way.' Jelly Roll won three Grammys at the 68th Annual Grammy Awards on February 1, 2026. CBS Photo Archive/CBS via Getty Images 'I was afraid that anything I was going to say was going to be immediately taken as a political statement. And ironically, by trying so hard not to make a political statement, I became one,' he added. 'I spent my entire career trying not to belong to a political party. Partly because until March of this year, I wasn't even allowed to vote. But now that I have that right, it's one I plan to exercise this coming November.' Previously, Jelly Roll was widely speculated to be a MAGA supporter. The theory largely stemmed from him shaking hands with Trump at a Madison Square Garden UFC fight in 2024. He clarified this incident during the monologue, saying, 'I'm proud that I was able to shake the president of the United States' hand. I'm also proud that I live in a country where I can make jokes about him. Ain't that what's great about being an American? The democracy, the freedom, the freedom of speech.' 'I'm proud that I was able to shake the president of the United States' hand. I'm also proud that I live in a country where I can make jokes about him," said Jelly Roll. Randy Holmes/Disney via Getty Images The rapper said that both sides of the political spectrum claim they want free speech 'until they hear something they don't want to hear.' His Kimmel stint deeply triggered Trump fans, with several loyalists complaining about his jokes, threatening to boycott his music, and labeling him as a 'f---ing sellout.' Jelly Roll has stood by his take, telling Kimmel's audience he's going to continue 'speaking my truth.' Later, in a tribute to Kimmel on Instagram, he wrote, 'Here's what I know: human dignity isn't Republican or Democrat. Compassion isn't left-wing. Mercy isn't right-wing.' 'My daddy was a Democrat. His brother was a Republican. Best friends till the day he died. Before he passed he told me: 'we agreed about hundreds of things. We weren't gonna let the few things we disagreed on define our relationship,'' he continued. 'A handshake ain't an endorsement. A joke ain't a political stance. And loving your neighbor doesn't come with an asterisk. Tomorrow I'm gonna try a little harder to love my neighbor. Hope y'all do the same. 🖤' He thanked Kimmel for welcoming him. 'What a week🖤.'