Jelly Roll shocked fans by roasting President Donald Trump while serving guest-hosting duties during Jimmy Kimmel Live on Monday night.The 41-year-old rapper-singer noted how the 80-year-old Republican politician reportedly gained 14lbs, ‘which means he’s now tipping the scales at almost 240.”In the last few years I’ve lost 300lbs. That means I’ve lost an entire Donald Trump,’ Jelly Roll (born Jason Bradley DeFord) said during his opening monologue.’And let’s be honest, based on his approval ratings, it seems like most of the country wants to do the same thing.’The three-time Grammy winner – whose top weight was 550lbs – finally reached his 265lb goal weight last November, and he still hopes to shed another 40-50lbs off his 6ft1in frame before running in the 26.2-mile New York City Marathon.After showing the audience a sizzle reel of Trump calling people ‘fat pigs’ like former New Jersey governor Chris Christie, he quipped: ‘Well, if that ain’t the pot calling the kettle fat.’ Jelly Roll shocked fans by roasting President Donald Trump while serving guest-hosting duties during Jimmy Kimmel Live on Monday night The 41-year-old rapper-singer noted how the 80-year-old Republican politician (pictured Monday) reportedly gained 14lbs, ‘which means he’s now tipping the scales at almost 240”Well, Mr. President from one fat pig to another, take it from me that physical fitness is very important. And trust me, you’ll be happy to see your penis again,’ Jelly Roll said.’I do speak from a little bit of experience here, y’all. The first time I seen mine recently, I was surprised at how cute it was. It kind of looked like a little Labubu doll.’The Nashville native also mocked the former reality star’s ‘s*** job’ at waving a green flag during the NTT IndyCar Series Freedom 250 Grand Prix in Washington, DC last Saturday.’The President seemed to enjoy the indie car race, which was a real switch up for him because normally he only likes his own race,’ Jelly Roll joked.On the Kimmel YouTube account, fans were confused about the heavily-tattooed millennial’s remarks like user @4MixMasterMonkey who commented: ‘Wait, hold up. Isn’t Jelly Roll MAGA?”Um wow I was not expecting him to trash talk trump,’ YouTube user @AnimaSola3o4 agreed.’LOL this was funnier than I expected,’ YouTube user @Paradoxical_Duality commented.’I think Jelly Roll did a great job,’ YouTube user @dorotheadelvalle121 wrote. ‘Hilarious!’Indeed, Jelly Roll previously gushed over his ‘powerful’ close encounter with Trump in 2024 during the UFC 309 event at Madison Square Garden in New York City.’There’s not a chance in hell I’m not going to meet the president-elect. I don’t care…if I would have got a call to go meet Joe Biden at any point, I would have stopped what I was doing to go meet him. That’s the active president. I wouldn’t have cared what people thought,’ the Hands Up singer said on the Dumb Blonde podcast at the time. ‘In the last few years I’ve lost 300lbs. That means I’ve lost an entire Donald Trump,’ Jelly Roll (born Jason Bradley DeFord) said during his opening monologue. ‘And let’s be honest, based on his approval ratings, it seems like most of the country wants to do the same thing’ 2026 vs 2021: The three-time Grammy winner – whose top weight was 550lbs – finally reached his 265lb goal weight last November, and he still hopes to shed another 40-50lbs off his 6ft1in frame before running in the 26.2-mile New York City Marathon After showing the audience a sizzle reel of Trump calling people ‘fat pigs’ like former New Jersey governor Chris Christie, he quipped: ‘Well, if that ain’t the pot calling the kettle fat’ ‘Well, Mr. President from one fat pig to another, take it from me that physical fitness is very important. And trust me, you’ll be happy to see your penis again,’ Jelly Roll said. ‘I do speak from a little bit of experience here’ The Nashville native also mocked the former reality star’s ‘s*** job’ at waving a green flag during The Freedom 250 Grand Prix in Washington, DC last Saturday ‘The President seemed to enjoy the indie car race, which was a real switch up for him because normally he only likes his own race,’ Jelly Roll joked On the Kimmel YouTube account, fans were confused about the heavily-tattooed millennial’s remarks like user @4MixMasterMonkey who commented: ‘Wait, hold up. Isn’t Jelly Roll MAGA?’ ‘Um wow I was not expecting him to trash talk trump,’ YouTube user @AnimaSola3o4 agreed ‘LOL this was funnier than I expected,’ YouTube user @Paradoxical_Duality commented ‘I think Jelly Roll did a great job,’ YouTube user @dorotheadelvalle121 wrote. ‘Hilarious!’ Indeed, Jelly Roll previously gushed over his ‘powerful’ close encounter with Trump in 2024 during the UFC 309 event at Madison Square Garden in New York City The Hands Up singer said on the Dumb Blonde podcast at the time: ‘There’s not a chance in hell I’m not going to meet the president-elect. I don’t care…if I would have got a call to go meet Joe Biden at any point, I would have stopped what I was doing to go meet him. That’s the active president’ He continued: ‘My father didn’t push voting on me. My mother didn’t push voting on me. They did push, “respect our president” on me, though. That’s the hardest job in the world. Respect whoever has it, you know?’ Jelly Roll will be filling in all week for his Idaho fishing buddy Kimmel (L), who remains on his annual summer vacation until September 8 During his July 30 concert in Utah, the ex-con announced he’d be taking a hiatus from performing for ‘a year or two’ in order ‘to take some time off and heal’ following his divorce from wife Alyssa ‘Bunnie Xo’ DeFord (R, pictured February 1) ‘I don’t hide behind the “I’m not political” stuff — I’m not political!… I like to talk about things I’m passionate about. With that, I like to know about them. I don’t know enough about politics to act like I know anything that’s going on, what anybody’s standing for policy-wise.’I genuinely don’t know. I didn’t grow up in a voting culture. My father didn’t push voting on me. My mother didn’t push voting on me. They did push, “respect our president” on me, though. That’s the hardest job in the world. Respect whoever has it, you know?’The Daily Mail has reached out to Jelly Roll’s reps for comment but did not immediately hear back.The Star Search judge will be filling in all week for his Idaho fishing buddy Kimmel, who remains on his annual summer vacation until September 8.During his July 30 concert in Utah, Jelly Roll announced he’d be taking a hiatus from performing for ‘a year or two’ in order ‘to take some time off and heal’ following his divorce from wife Alyssa ‘Bunnie Xo’ DeFord.However, the ex-con and the 46-year-old Stripped Down author – who were married for a decade – vow to amicably co-parent their future child, who is incubating in ‘the most unselfish, sweetest’ surrogate.Jelly Roll previously welcomed his 18-year-old daughter Bailee Ann DeFord with ex Felicia Beckwith and his son Noah Buddy DeFord, 10, with ex Melisa Ann Cowell.