Jelly Roll Jokes He Was the 'Worst Criminal Ever' as He Recalls Getting Arrested While on Xanax

"My successfulness of running from the police is zero and 20," said the country star, who's been arrested around 40 times

<p>Jason Kempin/Getty Images</p> Jelly Roll in New York City on June 12, 2024

Jason Kempin/Getty Images

Jelly Roll in New York City on June 12, 2024

It's a good thing Jelly Roll left his life of crime behind him — because he admittedly wasn't very good at it.

During a new interview on The Howard Stern Show, the 39-year-old country star reflected on his time spent dealing drugs and getting arrested, detailing one specific run-in with police that illustrates his point.

"You must have been the worst drug dealer because you were busted like 47 times," said host Howard Stern on the SiriusXM radio show.

Related: Jelly Roll Grows Emotional as He Visits His Old Cell in a Nashville Detention Center: 'I Never Thought I'd Lay Down Here'

"So bad," responded Jelly. "I was the worst criminal ever."

"My successfulness of running from the police is zero and 20," explained the "Need a Favor" singer. "But I was probably 15 years old, and I got arrested once, and I was on a Xanax bar — Howard, [I've] never told this story, but you know how Xanax make you a little slow anyways?"

"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 and sprinted across a field and almost made it," recalled Jelly. "I was so fat and Xanaxed out, I stood out and got two steps."

<p>Omar Vega/WireImage</p> Jelly Roll in Frisco, Texas in May 2024

Omar Vega/WireImage

Jelly Roll in Frisco, Texas in May 2024

"The cop was standing there watching me, and I fell. And he finally, he just laid on top of me," said the Grammy-nominated musician. "He felt so bad for me, he didn’t even charge me for trying to run."

In the new documentary Rebel Country, which premiered June 10 at Tribeca Festival, Jelly reflected on his frequent run-ins with the law as he visited his old detention center.

"Holy s---," he said while walking into the Metro-Davidson County Detention Facility in Nashville.

Related: Jelly Roll Says He's Scared of His Kids Encountering Fentanyl When 'Experimenting with Drugs' (Exclusive)

<p>Kevin Mazur/Getty</p> Jelly Roll in Los Angeles in February 2024

Kevin Mazur/Getty

Jelly Roll in Los Angeles in February 2024

“At the age of 14 I started making a series of decisions that led to what I call the revolving door of the judicial system," Jelly added. "So I would say from 14 to 24, I spent eight, eight and a half of those incarcerated. Come home for six months and go back to jail for a year."

The "Save Me" performer then cried as he entered his old cell. "I never thought I’d lay down here [again]," he said while laying down on his bunk bed.

"It’s crazy, man," reflected Jelly in the film. "When I started to get my head on straight and started dreaming, I quit looking out these windows and seeing barbed wire. I started seeing success."

If you or someone you know is struggling with substance abuse, please contact the SAMHSA helpline at 1-800-662-HELP.

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