Jelly Roll Recalls Being Incarcerated at 13, Says He Was 'Still a Bad Person' in His Early 30s: 'The Entitlement I Had'

Award-winning country music star Jelly Roll acknowledges the past experiences that made him —and he still wants to make amends.

On this week's episode of On Purpose with Jay Shetty, the 39-year-old singer gets candid about his criminal history, which began at an early age.

"It's deep-rooted insecurities early. I was always a bigger kid," Jelly remembers from his childhood. "So I had a little chip on my shoulder naturally as a young kid." While navigating his life in Antioch, Tennessee in an "active" neighborhood, the singer said he looked for "acceptance," and "the streets will always give it to you."

As for what landed him in jail, Jelly explains, "I'd gotten a fight with a kid and back then they had the chain wallets. 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 still holds guilt for his past, telling Shetty: "I look back at those years, Jay, and I'm so embarrassed to talk about them. 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.'"

He even hopes to make amends with his robbery victim over 20 years later and has a list of people to apologize to, but "I just haven't made it that far down yet."

"No matter how old I was, I had no business taking from anybody," the singer said. "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."

Jelly also reflected on his late father, who died in 2019. While the two always had a tight bond, it was after the singer escaped the "revolving cycle of the judicial system" that they got even closer.

"Me and him started really getting close and I started leaning on him and we would go to happy hour three or four days a week, every day. And we'd go sit at the same spot at the same bar and the memory and street in Nashville called the Tin Roof from 4 to 6."

His mother, who dealt with drug addiction and mental health issues, also had an impact on Jelly's future. "She started becoming really reclusive. There was a 20-year period in my life that I didn't see my mother outside of a nightgown, but maybe twice ever," he recalled. "But I connected music with her mental health, right? Because the few times when she was out of that bedroom and at that kitchen table, she was thriving."

The pair bonded over music, especially as Jelly's music career began to take shape. "When she seems her healthiest, there's always music playing. There's always this record player...it got to the point where if she was downstairs with her girlfriend, she'd call me up there to read whatever [song] I wrote was. Looking back now, you don't realize how much that feeds."

Jelly Roll is also a proud father and hopes to teach his two children Bailee Ann, 16, and Noah, 7, to learn from his mistakes. "She's going to be everything I wasn't in life," he said of his teenage daughter.

"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. 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, you know?"

Jelly recently took home a People's Choice Country Award for his “Lonely Road” collaboration with mgk. The duo reimagined John Denver's classic "Take Me Home, Country Roads" for a new audience.

You can catch Jelly Roll on his Beautifully Broken tour, which wraps up Oct. 27 in Charlotte, North Carolina.