Singer-songwriter Jelly Roll topped Billboard’s Mainstream Rock Airplay chart with “Dead Man Walking” in May 2022, hit No. 1 on Country Airplay seven months later with “Son of a Sinner,” and went on to spend a record-setting 28 weeks atop the Emerging Artists chart. The Nashville-area native has sold-out shows at both Nashville’s Ryman Auditorium and Bridgestone Arena; he also took home multiple honors at the CMT Music Awards in April. Now, he’s on the cover of this year’s Billboard Country Power Players issue. On Friday (June 2), he will release the full-length project, Whitsitt Chapel.

During his cover story interview with Billboard‘s Melinda Newman in Nashville, Jelly Roll opened up about his journey from spending time behind bars to selling out arenas and topping the charts in multiple genres. Jelly Roll spoke of how, at age 16, he was arrested for aggravated robbery and charged as an adult.

“I never want to overlook the fact that it was a heinous crime,” he told Billboard. “This is a grown man looking back at a 16-year-old kid that made the worst decision that he could have made in life and people could have got hurt and, by the grace of God, thankfully, nobody did.”

He also expressed a lingering bitterness over how the judicial system offered him such little opportunities for rehabilitation, despite his young age. Jelly Roll was facing a potential 20-year sentence, though he ultimately served over a year for the charge, followed by more than seven years of probation.

“They were talking about giving me more time than I’d been alive,” he told Billboard. “I hadn’t hit my last growth spurt. I was charged as an adult years before I could buy a beer, lease an apartment, get a pack of cigarettes … I feel like the justice system at that point kind of parked me on my only set path.”

Given Tennessee’s zero-tolerance policy for violent offenders, the charge is still on Jelly Roll’s record, and thus has lingering repercussions. Jelly Roll cannot vote, volunteer at most nonprofits or own a firearm. Until recently, he also could not get a passport, which impacted his ability to tour internationally. He also told Billboard about his attempt to buy a home in a gated community with its own golf course (Jelly Roll is an avid golfer); he was ultimately rejected.

“Imagine changing your life in such a way that you can afford the kind of house in this community I was looking at,” he told Billboard. “My money was welcome, but I wasn’t, all because of something I did [almost] 24 years ago.”

He recalls the moment he began to turn his life around, after learning of the birth of his daughter, Bailee. When he was 23, Jelly Roll was incarcerated for drug dealing. Then, on May 22, 2008, he learned that his daughter had been born.

“I’ve never had nothing in life that urged me in the moment to know that I had to do something different. I have to figure this out right now,” he said.

He was transferred from the violent offenders’ unit to the education unit and began studying for his GED, passing the test on his first attempt. After his release, he met his daughter on her second birthday. Bailee now resides with Jelly Roll and his wife, Bunnie, whom he married in 2016. He calls Bunnie “a beacon of change in my life. You’re talking about a woman that came in and took a child that was soon to be born and a child that [we were] soon to have full custody of,” he says. “I would have never got custody of my daughter without her. I wouldn’t have had the stability or the money.”