Hosting "Jimmy Kimmel Live!" for the second time but wearing a suit and tie for the first time, country singer, Jelly Roll, received several rounds of laughter and applause, mostly for his digs at President Donald Trump.
On Aug. 22, Trump attended the IndyCar Freedom 250 Grand Prix
in Washington, D.C., taking an honorary lap with first lady Melania Trump in the presidential limousine, and Jelly Roll definitely had opinions."But the president seemed to enjoy the IndyCar Race, which was a real switch up for him because normally he only likes his own race," Jelly Roll said through a smile.
Jabs at Trump continued throughout Jelly Roll's opening.
"Sadly, those are the only laps Trump's been doing lately," Jelly Roll said. "A lot of doctors are worried
about the president's weight."
Jelly Roll said Trump is pushing 240 pounds, which is less than the 300 pounds Jelly Roll has lost in the past couple of years.
"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 said.
Besides Trump, Jelly Roll pokes fun at himself during 'Jimmy Kimmel Live!' monologue
Jelly Roll's comments didn't stop there. He encouraged the audience not to make fun of the president's weight gain because he would never do that to others followed by a clip of Trump saying things like, "He's got the biggest stomach I have ever seen," and "The governor is a big, fat, slob."
The jokes didn't stop at Trump; Jelly Roll had some fun with jokes about himself too.
"Now you may know me from my hit songs, 'Need a Favor,' 'Save Me' and 'I Am Not OK,' which are all the things Jimmy said to get me to do this in the first place," Jelly Roll said.
He also said he had never worn a suit and tie before, not to the Grammys, a funeral or even in court.
"I didn't know that you could buy formal wear at a Bass Pro Shop," Jelly Roll said, resulting in more laughter.
The country music star also shared photos of himself and Kimmel on a recent fishing trip in Idaho.
"It looks like I started dating my parole officer," Jelly Roll said.
Watch Jelly Roll on 'Jimmy Kimmel Live!'
Nashville native Jelly Roll's journey from prison to Grammy win
Born Jason DeFord, Jelly Roll has become one of the biggest names in country music in just the last few years, despite being in the music industry since 2011. He is a Nashville native and grew up in Antioch, according to his Billboard biography.
Jelly Roll's song "Son of a Sinner" was his first song to make the Billboard Hot 100, making the list in 2022. Since then, several more of his songs, including "Save Me," which features Lainey Wilson, "Halfway to Hell" and "Heart of Stone," have made the Hot 100.
The singer has been nominated for seven Grammy Awards and has won three, all of which came at the 2026 Grammy Awards. Despite now being the winner of Best Contemporary Country Album for "Beautifully Broke," Jelly Roll faced a long road to get there.
Jelly Roll wasfirst arrested in 2002 at age 18. He was formally charged by Davidson County prosecutors with two counts of aggravated robbery and sentenced to eight years in prison, then seven years of probation.
The Tennessee Department of Corrections released him early, but Jelly Roll was arrested again in 2008. He was arrested for violating the Drug-Free School Zone Act. Later that year, he pleaded guilty to possession with intent to sell cocaine. He was sentenced to eight years in prison and eight years of probation, but his probation ended Dec. 16, 2016.
In 2025, Gov. Bill Lee pardoned Jelly Roll for two felony convictions.
Jelly Roll is now astaunch advocate against drug use. In 2024, he testified before the United States Senate's Committee on Banking, Housing and Urban Affairs during a hearing titled "Stopping the Flow of Fentanyl: Public Awareness and Legislative Solutions."
During a recent tour stop in Salt Lake City, Jelly Roll said he would be taking time off from touring and being in the public eye. The announcement came after news broke about his divorce from media personality Bunnie XO, his wife of nearly 10 years.
Afton Pratt covers trending news for The Knoxville News Sentinel and Tennessee. She can be reached at ampratt@usatodayco.com.
This article originally appeared on Knoxville News Sentinel: Jelly Roll roasts Trump, jokes about his weight loss on 'Jimmy Kimmel Live!'
