Jelly Roll was just 13 years old the first time he was incarcerated. The sentence, for robbery, was the beginning of more than a decade in and out of jail, and included being charged with a felony when he was just 16 years old.

“I’d gotten a fight with a kid and back then they had the chain wallets,” Jelly Roll recalls on the On Purpose with Jay Shetty podcast (via People). “When we were wrestling, I grabbed a chain wallet to try to hit him with it, and that was a strong-arm robbery case. So I ended up in the system for like 20-something months when I was 13 for that strong-arm robbery.”

Jelly Roll can, at least now, give himself a little bit of grace for the poor choices he made as a child. The son of a woman who struggled with mental illness, Jelly Roll in hindsight that his upbringing wasn’t conducive to making good life choices.

“It’s deep-rooted insecurities early. I was always a bigger kid. So I had a little chip on my shoulder naturally as a young kid,” Jelly Roll recalls, adding that it was the streets where he found acceptance. Still, even with that knowledge, the 39-year-old struggles to come to terms with the choices he made.

“No matter how old I was, I had no business taking from anybody,” Jelly Roll acknowledges. “Just this entitlement that I had that the world owed me enough that I could come take your stuff. What a horrible, horrible way to look at life and people, just what a horrible way to interact with the earth.”

 

It was the birth of his daughter, Bailey, now 16, which became the inspiration Jelly Roll needed to make a permanent change in his life. But even as he understands that he wasn’t given the tools necessary to make good choices, it does little to assuage the guilt of his past.

“I look back at those years, and I’m so embarrassed to talk about them,” the “I Am Not Okay” singer says. “I was still a bad person in my early 30s, but I mean, I was a really horrible kid all the way into my mid-20s. People are always like, ‘You’re the nicest dude I’ve ever met.’ I’m like, ‘I’m so glad y’all haven’t met nobody that knew me 20 years ago.'”

Jelly Roll, who is still trying to get his felony expunged from his record, at least feels some measure of pride at what it took for him to get to where he is today, both personally and professionally.

“I’ve been able to do the work and forgive myself for being that, for being what I was, but I definitely did a lot of work to change my whole outlook on people and love… I didn’t cry until I was 33,” Jelly Roll concedes. “Now I can’t quit. I mean, it’s like, I thought I’d caught up by now, but I mean, I still just, just for no reason, I’ll just sob.”

Jelly Roll’s Beautifully Broken album, along with the deluxe Beautifully Broken (Pickin’ Up the Pieces), are both out now.