Country music star Jelly Roll returned to Jimmy Kimmel Live! as guest host on Monday, and he didn’t hold back. The Grammy winner used his opening monologue to take repeated, scathing shots at President Donald Trump—covering everything from Trump’s flag-waving skills to his reported weight gain, and even suggesting the president would be “happy to see your penis again.”
The monologue, which drew laughs from the studio audience but reportedly caught many viewers off guard, followed in the footsteps of previous guest hosts like Anthony Anderson and Rosie O’Donnell, who similarly used their time on the late-night show to target Trump. But Jelly Roll’s approach was notably more personal, blending his own weight-loss journey with direct, unvarnished insults at the president.
Flag-Waving Fail
Jelly Roll, the “Son of a Sinner” singer, kicked off his monologue by referencing the Freedom 250 Grand Prix in Washington, D.C., which took place on Sunday. The race, hosted by the president as part of America’s semisesquicentennial celebrations, featured cars driving through the streets of the capital. Jelly Roll zeroed in on a video of Trump waving a flag during the event.
“The cars drove through the streets of D.C., and there’s Donald Trump who apparently has never held a flag before,” Jelly Roll said. “What a shit job!” he added, reacting to the footage. “How do you fuck up waving a flag?”
The singer also took a jab at Trump’s known admiration for racing, but suggested the president’s interest was a new development. “But the president seemed to enjoy the IndyCar race, which was a real switch up for him, ’cause normally he only likes his own race,” Jelly Roll quipped.
Lap of Honor, or Strip-Club Perk?
Trump also took a ceremonial lap around the track in his motorcade, which the president and his team often refer to as a “lap of honor.” Jelly Roll saw an opportunity for a distinctly crude metaphor.
“Trump also drove around the track in his motorcade, doing what they call the lap of honor, which sounds like a loyalty program at a strip club,” Jelly Roll joked. “Five percent cash back in the champagne room for all Lap of Honor members.”
The lap joke set up what became the most personal segment of the monologue: a series of fat jokes aimed at the president, based on a Washington Post report about Trump’s purported weight gain.
‘I’ve Lost an Entire Donald Trump’
Jelly Roll, who has been open about his own dramatic weight loss over the past few years, used the Post report to draw a striking comparison.
“It’s crazy. Think about this, y’all. In the last few years, I’ve lost 300 lb. That means I’ve lost an entire Donald Trump,” the singer said. “And let’s be honest, based on his approval ratings, it seems like most of the country wants to do the same thing.”
He then threw to a montage of Trump joking about other people’s weight, a clip that Jelly Roll used to pivot to his own message—though not without another pointed jab.
“Well if that ain’t the pot calling the kettle fat,” Jelly Roll said. “You know Mr. president, from one fat pig to another, take it from me, physical fitness is very important. Trust me, you’ll be happy to see your penis again.”
The line drew a mix of laughter and groans from the audience, and social media reactions were quick to split along familiar partisan lines. But according to media reports, the most notable reaction was surprise that Jelly Roll—a country artist often associated with more conservative-leaning audiences—was so willing to go after Trump so directly.
Reactions and Backlash
The Wrap, an entertainment trade publication, captured the mood with a headline: “Jelly Roll Stuns ‘Jimmy Kimmel Live’ Audience With Multiple Jabs at Trump: ‘Didn’t See This Coming.’” The report noted that while the monologue was well received by the studio audience, many viewers at home were taken off guard by the intensity and personal nature of the attacks.
This wasn’t Jelly Roll’s first time in the Kimmel guest-host chair—he previously filled in for the late-night host—but this appearance was markedly more political than his earlier stint. Jelly Roll has historically been less vocal about his political views, focusing instead on personal storytelling and themes of redemption in his music.
The monologue also sparked commentary about the intersection of entertainment and politics, with some noting that celebrity guest hosts are increasingly using their platforms to opine on current events, regardless of the host’s usual tone. Others pointed out that Jelly Roll’s weight-based insults, even when aimed at a president, might reflect a double standard given his own history with body image.
Neither the White House nor Trump’s representatives have publicly responded to Jelly Roll’s comments as of this writing.
Jelly Roll is not the first Jimmy Kimmel Live! guest host to use the spotlight for political criticism. Earlier this year, Anthony Anderson and Rosie O’Donnell both devoted significant portions of their openings to attacking Trump on various fronts. But Jelly Roll’s unique delivery—combining self-deprecating humor with sharp, sometimes crude barbs—set this monologue apart.
As the late-night hosting carousel continues to spin, Jelly Roll’s appearance will likely be remembered as one of the more memorable—and polarizing—guest-hosting spots of the season.
Source: www.breitbart.com — https://www.breitbart.com/entertainment/2026/08/25/jelly-roll-unleashes-penis-jokes-fat-jokes-on-trump-in-jimmy-kimmel-live-hosting-return-fat-pig/