Jelly Roll was "still a bad person" in his early 30s after being jailed aged 13.
The 39-year-old country music star has reflected on his criminal history and early struggles with the law, which stemmed from "deep-rooted insecurities" due to his weight as he tried to find "acceptance" wherever he could find it.
He told 'On Purpose with Jay Shetty': "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."
The 'Save Me' hitmaker admitted he still feels guilty for what happened, and he insisted he was "a really horrible kid" until his mid-20s.
He added: "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.' "
Jelly wants to apologise to his robbery victim over two decades later, but he hasn't "made it that far down" his list yet.
He added: "No matter how old I was, I had no business taking from anybody. 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."
And the proud father-of-two wants his children Bailee Ann, 16, and Noah, seven, to learn from his past mistakes.
He said: "She's going to be everything I wasn't in life...
"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?"
