Jelly Roll looked back on his criminal history and past experiences, which made him the "nicest dude" he is today.

During his appearance at this week’s episode of On Purpose with Jay Shetty, the Award-winning country music sensation opened up about what led to his first incarceration at an early age.

"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," the 39-year-old rapper explained. "So, I ended up in the system for like 20-something months when I was 13 for that strong-arm robbery."

Jelly Roll, whose real name is Jason Bradley DeFord, told Shetty, 37, that he still carries guilt from his past, a feeling that has profoundly humbled him and influenced his character today.

"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," says the Son of a Sinner vocalist, who has been married to his wife, Alyssa DeFord, known as "Bunnie XO", since 2016.

"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 added.

Additionally, Jelly Roll has plans to make amends with his robbery victim over 20 years later and has a list of people to apologise to, but "I just haven't made it that far down yet."