Jelly Roll makes no secret of his criminal past, but that doesn’t mean he was actually good at it. In a new interview with Howard Stern, the rapper turned country superstar shared a hilarious story about running from the police when he was 15 years old, ruefully admitting that he wasn’t a particularly skillful criminal.

Jelly Roll appeared on The Howard Stern Show on SiriusXM on Wednesday (June 12). The singer spent years in juvenile detention and prison before completely turning his life around, prompting Stern to ask, “How did you get caught so much?”

“I was the worst criminal ever,” Jelly Roll replied with a laugh. “My successfulness of running from the police was zero in 20.”

For example, he shared a story from when he was 15 and got arrested while high on Xanax.

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“You know how Xanax makes you a little slow anyways?” he asked. “In my mind when the police pulled us over, I was like, ‘I’m just gonna run.’ So I opened the door, and in my mind, I jumped out [of the car], sprinted across the field and almost made it.”

The reality was very different, he shared.

“I was so fat and Xanax-ed out I stood out and got two steps,” he recalled, laughing. “The cop was standing there watching me, and I fell, and he just laid on top of me.”

Jelly Roll’s criminal incompetence actually had a silver lining, he explained.

“He felt so bad for me that he didn’t even charge me for trying to run.”

Elsewhere in the interview, Jelly Roll talked about life in prison, where he said getting into fights with other inmates was unavoidable. He often dreamed about a future in music while incarcerated, using his steel bed as a drum to create beats while he worked on some of his earliest songs.

Though Jelly Roll can look back now and laugh, his criminal past still follows him, despite all of his work to help at-risk youth and those who are currently incarcerated turn their lives around like he has.

In 2023, the singer revealed he had lost out on his dream house because the homeowner’s association would not allow a felon to live in that neighborhood, and he’s still struggling to find a way to tour overseas due to his past felony conviction.

His career has never been stronger, however; Jelly Roll just scored his fourth consecutive No. 1 hit on Billboard‘s Country Airplay Chart with “Halfway to Hell,” and his upcoming 2024 Beautifully Broken Tour is one of the most-anticipated country tours of the summer.

Sterling Whitaker is a Senior Writer and Senior Editor for Taste of Country. He focuses on celebrity real estate, as well as coverage of Yellowstone and related shows like 1883 and 1923. He’s interviewed cast members including Cole Hauser, Kelly Reilly, Sam Elliott and Harrison Ford, and Whitaker is also known for his in-depth interviews with country legends including Don Henley, Rodney Crowell, Trace Adkins, Ronnie Milsap, Ricky Skaggs and more.