Going all in.
Country singer Jelly Roll is serving as a guest host on Jimmy Kimmel Live! this week, and he created quite the firestorm after using his first monologue on Monday to take some shots at President Donald Trump.
Now, I’m sure the jokes were probably written by the show’s writers who don’t really know how to write about anything else, but Jelly Roll started by joking about the president waving the green flag at the Freedom 250 IndyCar event in Washington, D.C. this past weekend, before turning his attention to Trump’s weight:
“In the last few years I’ve lost 300 pounds. 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… 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 has never been especially political, and in fact has said in the past that he doesn’t identify with either political party because he lost his right to vote as a convicted felon. But he’s also been spotted shaking hands with Trump before, during a UFC event back in 2024, and is often branded as “MAGA” by left-wing media.
Well naturally, there was plenty of backlash over his first night as guest host, with many on the right criticizing him for taking the easy bait when he’d previously refused to talk politics. But Jelly Roll addressed the critics on Tuesday, though he was far from apologetic:
“It’s because I’m hosting a damn late night show. That’s where you talk about the news and you make jokes. But I guess apparently because I did it, it really messed with people’s heads.”
He even gave a shout out to frequent Trump critic (and last week’s guest host) Rosie O’Donnell before defending his jokes at the president’s expense:
“Some folks online were upset that I didn’t treat the president with reverence and dignity. But I want to remind y’all that I go by the name Jelly Roll. I don’t even treat myself with reverence and dignity. …
Frankly I think most people were just surprised that I had any opinions at all. They see a guy that looks like me and assume the only opinion I have is whether I prefer my meth crystal or classic.
Now let’s be honest for a second: Any US president should be able to handle a few jokes, right? They should also be able to handle gas prices, healthcare, and the occasional international conflict. Look y’all, I get it. Some people are mad at me for goofing on Trump. But if you wanted me to make jokes about Kamala Harris, you should have voted for her.”
And last night, he continued to take aim at the president, returning to the jokes about Trump’s weight while also taking aim at his trade policies with Canada.
He started his jokes about Trump after first discussing a recent incident in Los Angeles where a truck spilled 120 containers of cheeseballs on the interstate:
“Speaking of cheeseballs, let’s talk about Donald Trump.
The president is doubling down on his ridiculous trade war with Canada. And they’re saying this could lead to higher prices for several products, including whiskey, smartphones, but most alarmingly, toilet paper.
But you have to admit, there is something poetic about it being so expensive to wipe our a** just because the president’s full of s–t.”
Jelly Roll joked that he was really starting to feel like Kimmel because they were talking about his monologues on Fox News, playing a segment from host Jesse Watters accusing the singer of developing “Trump Derangement Syndrome” from taking Ozempic.
“I can’t believe out of all the jokes I’ve told the past few nights, the one that really seemed to make people mad about what I said about the president was when I said he was overweight. I thought fat on fat crime was okay? We can debate if this president is mentally fit, but I think we can all agree he is certainly not physically fit.
But I hope I can inspire the Donald, man. If I can lost all that weight, he can too. And in fact, there is a new medication on the market designed specifically for him.”
They went on to play an SNL-esque commercial for “Donjaro,” a once-daily injection for weight-loss management. Jelly ended the Trump portion of the monologue with a joke about the President’s thin skin, although Trump has yet to respond to the Jelly Roll jokes:
“Wouldn’t it be nice to see Trump lose something besides the war, his popularity, and most of his marbles? And just so we’re clear, I believe in you, Mr. President. With a little hard work, one day your waistline will be just as thin as your skin.”
Once again, let me remind you that Jelly Roll isn’t writing these jokes. All the Jimmy Kimmel staff knows how to do is rip on President Trump, so this is pretty par for the course, but it does make you wonder why Jelly Roll would want to inject himself into the noise and alienate fans. And then do it again? Granted, the joke was pretty soft and the Right is ironically the “why can’t you take a joke?” party, but it’s 2026… nuance and laughing at yourself have gone WELL out the window.
Jelly Roll addressed the backlash, basically saying that “it’s just late-night TV and you’re supposed to make jokes,” but late-night TV is a far cry from what it used to be… it’s not harmless fun anymore. It’s largely just partisan propaganda, and Jimmy Kimmel is one of the most left-leaning, liberal mouthpieces on TV. Should you be able to make jokes about any president? Yeah, for sure. But in this overly divisive and hypersensitive political climate, you already know that it’s not going to go over well with half of your audience… and it clearly hasn’t.
The lesson here is that not all opportunities are good opportunities, and sometimes saying “no” is the best course of action for someone’s career… this was probably one of those times. Jelly Roll’s likability comes from standing up for those who can’t stand up for themselves, being a voice for the voiceless, his powerful redemption story, and the message that you CAN change your life for the better. And it’s hard to argue that he hasn’t had a positive impact on his fans.
Which is why guest hosting for Jimmy Kimmel… an elitist, Hollywood jerk who regularly reveals how much he looks down on the kind of people Jelly Roll is making music for… is just so utterly perplexing. As dumb as it may be, Jelly Roll will absolutely lose fans over this… the shine is officially off the apple. You hate to see it…
