Kimmel Host Warned He Could Lose ‘Half’ His Fans Over Trump Jokes

SLOW YOUR ROLL

“He knows how this works,” a MAGA-supporting country star said.

Jelly Roll’s opinions on Donald Trump came as a surprise to some of the country music star’s fans—but another Trump-loving country star said Jelly’s jokes aimed at the president were not “surprising.”

John Rich, the country singer sworn into the Trump administration last month as its “Special Envoy for American Landowners,” said Jelly Roll should be prepared for any MAGA fans he might have had to “disown” him.

“The Jelly Roll situation is interesting to me because he presented himself, and I’ve been around him a long time, presented his story—had a horrible past, was incarcerated for a long time, turned his life around, came out into country music, really was a testimonial to second chances in America,” Rich said in an interview on The Benny Show.

NEW YORK, NEW YORK - NOVEMBER 16: Musical Artist Jelly Roll shakes hands with President-elect Donald Trump during the UFC 309 event at Madison Square Garden on November 16, 2024 in New York City. (Photo by Jeff Bottari/Zuffa LLC)
Jelly Roll was seen shaking Trump's hand at a UFC fight in 2024. Jeff Bottari/Zuffa LLC

“That America gave him the opportunity to turn his life around—life, liberty, and the pursuit of happiness. And a Republican governor in Tennessee pardoned him,” Rich added. “And then, of course, he was complimentary about the president.”

The three-Grammy winner changed course to some of his fans’ surprise while guest-hosting for Jimmy Kimmel.

In one brutal swipe at Trump’s weight and plummeting approval rating, Jelly Roll said, “A lot of doctors are worried about the president’s weight. After his last physical, we found out Trump gained 14 pounds, which means he is now tipping the scales at almost 240. That’s crazy.”

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Rich is an avid supporter of Trump's and joined the administration last month as his "Special Envoy for American Landowners." Michael Loccisano

He continued, “Think about this, y’all, in the few last years I’ve lost 300 pounds. That means I’ve lost an entire Donald Trump. And let’s be honest, based on his approval ratings, it seems like most of the country wants to do the same thing.”

Jelly Roll addressed backlash to his comments when he guest-hosted the show for a final night on Aug. 27: “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,” he said, because of his past felony convictions. “But now that I have that right, it’s one I plan to exercise this coming November.”

He also addressed speculation that Kimmel’s writers were behind his anti-Trump quips. “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,” he said. “But let’s be real about this, y’all. Do you think I would take orders from some sweaty little dork named Josh? No, I was just telling it like it is, and for some reason, that seemed to freak a lot of people out.”

Rich said Jelly Roll was well aware of the risks of revealing his stance on the president.

“When you come in and make statements like he did over the past week—he knows how this works,” Rich said. “He knows who the audience is. And so I have to think he really believes every single word he said, or he wouldn’t have said it because when you make statements that are that hardcore and to a large extent counteractive to the presentation you’ve been making, you do understand in country music that half or more of your audience may disown you.”

Jelly Roll won three awards at the 68th GRAMMY Awards: Best Country Duo/Group Performance for "Amen," Best Contemporary Country Album for "Beautifully Broken," and Best Contemporary Christian Music Performance/Song for "Hard Fought Hallelujah."
Jelly Roll won three Grammys this year. Jeff Kravitz/FilmMagic

He went, “They may turn their back on you, they may stop listening to you, they may turn you off, but you make the statement anyway.” Rich, an avid supporter of Trump’s, compared the backlash he received when he announced his support for Trump. “I’ve done the exact same thing in my career. I have made statement after statement, things that I’m for, things that I’m against, knowing that the entire music industry is liberal. They’re all liberal.”

Rich said he lost a record deal, radio play, and stopped being invited to awards shows. “All those things happened to me,” he said, “And so Jelly Roll knew the same thing concerning his audience, yet he did it anyway. So to me what that says is this guy is really who he says he is.”

The country singer also said he suspects Jelly Roll has felt this way about Trump longer than most would imagine. “I think what you’re seeing from the backlash is people didn’t know that’s who he really is and that that’s how he really thinks,” Rich said. “It’s not a crime or a sin to say what he said; it’s just a revealing thing. He should have been talking that way from the very beginning, and he probably wouldn’t have this problem.”

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