Jelly Roll caught viewers off guard with a string of jabs at President Trump while guest-hosting Jimmy Kimmel Live on Monday night, filling in for Jimmy Kimmel for the second year in a row during his summer hiatus.
Opening his monologue by noting it was his first time ever wearing a suit and tie, “I didn’t wear one to the Grammys. I didn’t wear one to court. I didn’t wear one to my father’s funeral. But I look all right, don’t I?”, the singer quickly turned his attention to Trump’s appearance at a recent IndyCar event in Washington, D.C.
“Let’s talk about the main event of America this weekend. It was the big IndyCar race hosted by the president,” Jelly Roll said, mocking Trump’s flag-waving 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. What a s*** job! How do you f*** up waving a flag?”
He also referenced Trump’s approval ratings, joking that the president “seemed to enjoy the IndyCar race, which was a real switch-up for him, because normally he only likes his own race.”
The singer then pivoted to a bit about Trump’s recent weight gain, citing reports that the president had gained roughly 14 pounds since his last physical.
Drawing on his own well-documented weight loss journey, Jelly Roll quipped, “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.”
Before making the joke, he pointedly noted that the audience shouldn’t stoop to mocking the president’s weight, “because we know that he would never do that to other people,” then ran a montage of Trump making similar comments about others’ appearances over the years, adding, “Well, Mr. President, from one fat pig to another, take it from me that physical fitness is very important.”
The monologue caught many viewers by surprise, given Jelly Roll’s public reputation as a MAGA-aligned artist.
Reactions poured in across social media, with one fan writing, “Wait, hold up. Isn’t Jelly Roll MAGA? I’m very confused right now,” while another simply noted, “Didn’t see this coming.”
The singer has previously said he doesn’t affiliate with any political party, and nothing in the broadcast suggested a formal political statement beyond the jokes themselves.
His guests for the night included podcast host Jay Shetty and actor Glen Powell, who revealed during the segment that Jelly Roll has a small onscreen singing role in his upcoming film The Comeback King, alongside Miranda Lambert and Brad Paisley.
