Country music artist Jelly Roll, the same tattooed “redemption” act who once lit up like a kid on Christmas when he met President Donald Trump, has now told his own fans to get lost if they don’t like him punching down at the President from Jimmy Kimmel’s Hollywood desk.
The three-time Grammy winner returned to Jimmy Kimmel Live! on Tuesday for his second night as guest host and immediately addressed the firestorm caused by his Trump-bashing monologue one night earlier.
Rather than apologize to the fans who helped build his career, Jelly Roll told them to take a hike.
Addressing listeners who threatened to boycott his music, the singer said he wanted to respond “with conviction.”
“Go right ahead,” Jelly Roll declared before insisting that he would continue “speaking my truth” and ending with a joke that his name was Post Malone.
Jelly Roll argued that he had merely done what late-night hosts are expected to do: talk about current events and make jokes.
He then claimed that any American president should be capable of handling comedy before launching into another attack on Trump over gas prices, health care, and international conflicts.
In other words, Jelly Roll’s answer to the backlash was to double down.
WATCH:
🔥🚨 BREAKING — Jelly Roll DOUBLES DOWN, tells fans to stop listening to his music if you don’t like what he said about President Trump.
“So for those who threatened to STOP listening to my music based on my comments last night, I just wanna say with conviction, GO RIGHT AHEAD!”… pic.twitter.com/zBQunnPmRG
— The Patriot Oasis™ (@ThePatriotOasis) August 27, 2026
The controversy erupted Monday when Jelly Roll used Jimmy Kimmel’s struggling late-night platform to unleash several personal and vulgar attacks against President Trump.
The singer made a racially charged joke about Trump attending the Freedom 250 Grand Prix IndyCar race in Washington, D.C., mocked the president’s approval ratings, and repeatedly attacked his weight.
Jelly Roll claimed that after losing 300 pounds, he had “lost an entire Donald Trump.”
He later referred to Trump as a “fat pig” in a self-deprecating comparison and made an obscene remark about the president’s anatomy.
This was not simply light political teasing. It was a calculated series of cheap personal attacks delivered to Jimmy Kimmel’s anti-Trump television audience.
As The Gateway Pundit previously reported, the spectacle was especially striking because Jelly Roll once appeared thrilled to meet Trump at UFC 309 in Madison Square Garden in November 2024.
Footage from the event showed Jelly Roll eagerly approaching then-President-elect Trump after Kid Rock introduced the two men.
Jelly Roll later defended that meeting on his former wife Bunnie Xo’s podcast, saying there was no chance he would pass up an opportunity to meet the president-elect.
“Meeting President Trump was cool,” he said at the time.
What a difference a Jimmy Kimmel teleprompter makes.
Jelly Roll has previously described himself as politically unaffiliated. During Senate testimony about the fentanyl crisis in January 2024, he said he was neither a Democrat nor a Republican and had never closely followed political races because his voting rights had been restricted due to his criminal history.
But his conservative fans were not angry merely because the entertainer told a political joke. They were angry because an artist who built a broad audience through songs about redemption, struggle, faith, and second chances suddenly used a far-left late-night stage to launch vulgar personal attacks against Trump.
Now, instead of acknowledging their disappointment, he is telling those fans that he does not need them.
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