Jelly Roll has used his week guest hosting Jimmy Kimmel Live to take repeated aim at Donald Trump, with the country star’s jokes about the president’s weight becoming the most contentious part of his late-night debut.
by Paul Cashmere
Jelly Roll has spent his first three nights as guest host of Jimmy Kimmel Live turning Donald Trump into a recurring target, with jokes about the president’s weight, physical fitness and appearance becoming the defining material of his week in the late-night chair.
The Nashville artist, whose real name is Jason DeFord, opened Monday’s programme by discussing Trump’s appearance at the Freedom 250 Grand Prix in Washington, DC, before shifting to the president’s reported weight gain. Jelly Roll said he had lost 300 pounds in recent years, joking that he had therefore “lost an entire Donald Trump”. He then linked the joke to Trump’s approval ratings, saying much of the country appeared to want to do the same.
The material continued on Tuesday, when Jelly Roll responded directly to the reaction his Trump jokes had generated. “Any U.S. president should be able to handle a few jokes,” he said, arguing that political commentary is part of the job when hosting a late-night programme.
The weight jokes became considerably more pointed on Monday.
Jelly Roll referenced reports that Trump had gained 14 pounds since his previous physical and contrasted that with his own 300-pound weight loss. He then delivered a series of jokes built around the president’s size, including a reference to Trump as a “fat pig” and a line suggesting that improved physical fitness might make it easier for the president to see his penis.
The joke was particularly personal because Jelly Roll has made his own weight-loss journey a prominent part of his public story. He has previously spoken openly about his health and the physical effects of his former weight. On Kimmel, he used that experience as the basis for the comparison rather than presenting himself as an outsider commenting on another person’s body.
The following night, he returned to the subject with a parody pharmaceutical advertisement. The fictional drug, “Donjaro”, was presented as a weight-loss treatment supposedly designed for Trump, complete with exaggerated warnings about “massive cankles” and other invented side effects.
Jelly Roll also returned to the central joke about his own transformation. He said he was proud to have lost the weight through diet and exercise, while joking that he felt like someone who had bought a horse and buggy immediately before cars became available.
The jokes carry additional significance because Jelly Roll has not traditionally positioned himself as a political artist. His Trump material therefore surprised sections of his audience, particularly people who had assumed his country background and public image placed him firmly on one side of American politics.
Jelly Roll addressed that reaction directly on Tuesday. He joked that people were surprised he had political opinions at all and said that criticism of his appearance had perhaps led people to underestimate him.
He also dismissed threats from people who said they would stop listening to his music because of the jokes. His response was deliberately comic, saying he would continue speaking his truth, “or my name isn’t Post Malone”.
The ABC episode description confirms that the Trump material was a central part of the Monday broadcast, specifically identifying the president’s IndyCar appearance, concerns about his weight and Trump’s history of making comments about other people’s weight as subjects of Jelly Roll’s monologue.
Jelly Roll’s role comes against the backdrop of a long-running conflict between Trump and Jimmy Kimmel. Their relationship began in a considerably lighter environment, with Trump appearing on Jimmy Kimmel Live during his 2015 presidential campaign. The relationship deteriorated after Trump entered the White House, as Kimmel increasingly used his monologues to criticise Trump’s policies, conduct and public statements.
The dispute subsequently became personal. Trump repeatedly attacked Kimmel and other late-night hosts, while Kimmel continued to use Trump as a major source of political comedy. The conflict intensified around Kimmel’s 2024 Oscars hosting appearance and continued into Trump’s second presidency.
The show itself also became part of a wider political and media confrontation when ABC temporarily suspended Jimmy Kimmel Live in September 2025 before restoring it a week later. Trump publicly celebrated the suspension at the time. Kimmel has since remained one of the president’s most consistent late-night critics.
Jelly Roll is therefore occupying Kimmel’s chair at a particularly charged moment. ABC scheduled him as guest host for four consecutive nights from August 24 through August 27, with Kimmel on summer break.
The political jokes are only one part of Jelly Roll’s week. His monologues have also drawn heavily on his personal history, including his criminal record, former drug dealing, extensive face tattoos and dramatic weight loss.
On Wednesday, he continued the Trump material by discussing criticism from Fox News and joking about the suggestion that he had developed “Trump Derangement Syndrome”. He then returned to the subject of weight loss, again making his own transformation the reference point for jokes about Trump.
The broader significance is the unusual crossover. Jelly Roll has moved from country music into mainstream entertainment, while Kimmel’s programme has used celebrity guest hosts during the summer break. The format gives Jelly Roll an opportunity to demonstrate a different kind of performance skill while placing him in the middle of a political comedy tradition normally associated with Kimmel himself.
ABC has confirmed Jelly Roll is hosting through Thursday, August 27. The scheduled Thursday programme features Leslie Mann and Bert Kreischer, while the remainder of the week is subject to change.
For Jelly Roll, the most memorable part of the assignment may ultimately be the unexpected political turn. He entered Kimmel’s chair as a country star known primarily for songs about his own life. He has left the week having discovered that, for a few nights at least, Donald Trump’s waistline can generate as much attention as a hit record.
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