Jelly Roll will begin his headlining Beautifully Broken Tour in late August, but every time the 2024 Grammys nominee speaks about his past, he reminds everybody why his tour had to be called the Beautifully Broken Tour.

The latest example came during Wednesday’s (June 12) episode of The Howard Stern Show, where Jelly Roll discussed a wide range of topics, including a never-before-told story from his past defined by crime and arrests.

The Tennessee native born Jason DeFord confirmed to Stern that he became a drug dealer as an adolescent because it gave him “a purpose.” Then, Stern questioned Jelly Roll on getting “busted, like, 47 times.” Jelly Roll said, “Oh, so bad. I was the worst criminal ever.”

“My successfulness of running from the police is 0-20,” Jelly Roll continued. “I was probably 15 years old, and I got arrested once, and I was on a Xanax bar, Howard. Never told this story, but you know how Xanax make you a little slow anyway? In my mind, when the police pulled us over, I was like, ‘I’m just gonna run.’ So, I open the door, and in my mind, I jumped out [and] sprinted across a field and almost made it. I was so fat and Xanaxed out, I stood out, got two steps, the cop was standing there watching me. I fell, and he just laid on top of me. He felt so bad for me, he didn’t even charge me for trying to run.”

Jelly Roll also opened up about how he experienced prison, how he met his wife, which tattoos he regrets, and more. Watch the clips below.