Jelly Roll is looking at himself — and his past — in a whole new way.

The country superstar (real name Jason DeFord) kept it real in a new Men’s Health cover story, sharing how his tattoos — especially the ones on his face — represent a person he no longer is.

“When people say my look is a call for attention, it’s actually the polar opposite,” Jelly Roll said. “The way shame sometimes shows itself is not always the way we expect it to be. We think shame is somebody in the streets on their knees, with their head down. But shame sometimes is pride.”

He explained that behind his rough exterior and ink-covered skin was a deeply insecure man.

Read More: Jelly Roll Reflects on Life After 275-Pound Weight Loss: ‘Dramatically Different World’

“Behind real bravado, I can normally find shame. I can normally find guilt. I can normally find insecurity,” he shared. “I was the biggest, the loudest, the toughest, the meanest, the growliest, the fattest — and there was a really, really small, insecure human behind those walls.”

The “Save Me” singer even admitted he’s thought about removing some of his tattoos as part of his personal evolution — one that’s taken him from self-destruction to self-love.

Regret + Reflection

Jelly Roll has reflected on his tattoos before. In 2024, he told GQ that he regrets “almost all” of them, calling them remnants of a version of himself that doesn’t exist anymore.

“Like core philosophies are rooted in my life when I was 17 and now I’m 40, I’m like, ‘What the f— was I thinking?’” he said. “I hate them all.”

His new Men’s Health cover marks another turning point — one that extends far beyond tattoos and image.

A Transformation Inside + Out

The feature also celebrates a milestone Jelly Roll has been working toward for years: his physical transformation.

Read More: Jelly Roll: Pictures Show How Much Weight He’s Lost In 2025

In 2024, he set a goal to appear on the cover of Men’s Health, hoping to have “one of the biggest transformations” the magazine had ever seen.

Now, he’s done it.

Jelly Roll appears on the cover of the magazine’s Winter 2026 issue after shedding an incredible 275 pounds. He revealed that last year, he was consistently losing between 9 and 15 pounds a month.

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

The singer’s journey — also chronicled in a new Men’s Health documentary short titled A Year for a Life — shows that for Jelly Roll, the changes go far deeper than skin.

“I was 500-something pounds and walking a 40-minute mile,” he reflected. “Even to me, as wild as I think and big of a dreamer as I am, that was pretty ambitious.”

Today, the man once defined by his tattoos and his size is redefining himself on his own terms — one mile, one change, and one day at a time.