Jelly Roll Reaches Milestone Goal After 275-Lb. Weight Loss: ‘I’ve Worked Really Hard’

Jelly Roll is kicking off 2026 by reaching a life-changing milestone in his health journey.

Back in December 2024, the country singer shared an ambitious goal: to appear on the cover of Men’s Health by 2026, aiming for what he called “one of the biggest transformations.” Just over a year later, he’s made it happen.

The 41-year-old appears on the cover of Men’s Health’s Winter 2026 issue, published Jan. 2, after losing 275 pounds. He also stars in a new Men’s Health documentary short, A Year for a Life, which chronicles his physical and mental transformation.

“I’m loving my body,” Jelly Roll said. “This is a whole new thing for me, y’all. I’ve been imprisoned in a fat suit for 30-something years.”

Reflecting on the moment, he added, “I am on the cover of Men’s Health magazine. When I was 500-something pounds and walking a 40-minute mile, I was screaming that I was going to be on the cover of Men’s Health. Even for me — and I’m a big dreamer — that was pretty ambitious.”

At his heaviest, Jelly Roll weighed 540 pounds. He has spoken openly about how obesity and food addiction filled his life with shame and limited even basic daily activities.

“It was never-ending sadness. And anger,” he said. “I was a prisoner to my own body. Wiping myself was a problem. Washing properly was a problem. Getting into cars. Every decision I made had to be based on my weight — whether something could hold me, fit me, or support me. People don’t think about how every single part of life is affected.”

He described the emotional toll as deeply intertwined with addiction. “I was killing myself, literally. I was eating myself to death. I can’t think of one area of my life it didn’t touch,” he said. “Shame is the exact thing that sends me back into the pantry — the same way it sends an alcoholic back to the bar.”

After multiple unsuccessful attempts to lose weight, the Grammy-nominated artist finally found consistency by building a support system. He hired a chef and a sports nutritionist and began prioritizing movement as part of his daily routine.

In the documentary, Jelly Roll is seen boxing, playing basketball, running arena stairs, and taking on push-up challenges with friends. He also works daily with a physiotherapist to improve mobility.

“There’s this magical thing that happens when you get past the misery at the start of exercise,” he said. “In the middle of it, when it still sucks, something opens up — and you feel incredible. I can touch my toes now. I saw my kneecaps the other day standing up. That’s a whole new concept for me.”

Now weighing 265 pounds, Jelly Roll says his relationship with his body has completely changed. Once unable to look in the mirror without disgust, he now finds himself stopping to admire the muscle he’s built.

The “Son of a Sinner” singer also shared that he plans to have excess skin removed sometime next year.

While the scale no longer defines his progress, Jelly Roll says his journey isn’t finished yet.

“I don’t have a goal weight — I have a feeling weight,” he explained. “I’ll know when I feel it. But I’ve worked really hard and lost the weight the right way.”

“It’s just a dramatically different world.”