Country superstar Jelly Roll’s incredible weight loss journey has given him a new lease on life — and, finally, a new wardrobe. Kicking off his week as the guest host for “Jimmy Kimmel Live” on August 24, 2026, the former artist-in-residence on “American Idol” and judge on Netflix’s “Star Search” reboot wowed fans as he appeared in a navy suit with a coordinating tie and white pocket square — a major departure from his usual uniform of black pants with a black or denim shirt.
After Kimmel’s longtime sidekick Guillermo Rodriguez told the singer how “amazing” he looked, Jelly Roll said, “Y’all might not believe this, and it’s going to sound like a joke, but this is the first time I’ve worn a suit and tie — ever. I mean, I didn’t wear one for the Grammys, I didn’t wear one to court, I didn’t wear one to my father’s funeral. But I look alright, don’t I?”
Jelly Roll Says He Dressed Up in Jimmy Kimmel’s Honor
Fans cheered for Jelly Roll’s new look, which he finally felt confident wearing after dropping 300 pounds “in the last few years.” The Grammy winner has documented his health journey on social media as he changed his diet, worked out with trainers and even ran his first 5k in May 2024 at the Netflix Is a Joke Festival.
The country star said he wanted to dress up like Kimmel does for his show, joking, “I didn’t know that you could buy formal wear at a Bass Pro Shop, but I’m wearing this out of respect for my friend Jimmy Kimmel. I love you, Jimmy.”
Jelly Roll then shared photos from a recent fishing trip in Idaho with the late night host “so I can confirm he does not have a good reason not to be here tonight. Y’all would think he’s spending time with his family, working out, being productive. Not at all! He’s doing absolutely jack [expletive] right now.”
“We did have a great time together though,” he said before joking, “Look at that, y’all, there we are. It looks like I started dating my parole officer!”
Jelly Roll Addressed His Weight Loss During ‘Jimmy Kimmel Live’ Monologue
During his monologue, Jelly Roll celebrated his 300-pound weight loss while also poking fun at President Donald Trump’s figure.
“According to the Washington Post,” he began one joke, “a lot of doctors are worried about the president’s weight. After his last physical, we found out Trump gained 14 pounds, which means he’s now tipping the scales at almost 240. It’s crazy — think about this, y’all. In the last few years, I’ve lost 300 pounds. That means I’ve lost an entire Donald Trump!”
Fans were wowed by Jelly Roll’s transformation, flooding social media with comments about how good he looked in his first-ever suit and tie, including one who wrote, “I like this new and improved Jelly Roll 🙌🏽🫶🏽”
Another gushed, “He looks very handsome. Good for him 🔥🔥🔥 love Jelly Roll and he did a great job!! 👏👏”
Someone else wrote, “You did a great job! A singer and a comic! You look great! Your hard work has paid off. You look like a perfect fit behind the desk. Who knows what the future will bring. Will be watching all week! 👏🔥❤️”
Multiple guest hosts are filling in for Kimmel during his annual summer vacation from his late night show on ABC, including Tiffany Haddish, Anthony Anderson, and last week’s fill-in, Rosie O’Donnell.
