Before he was a regular at arenas, iconic venues, and on red carpets, Jelly Roll was a regular at various detention centers around Tennessee, police car back seats, and halfway houses. The rapper and country star has long been open about his lengthy tenure at the Metro-Davidson County Detention Facility in Nashville. This tumultuous time in his life has directly informed both the lyrics he writes and his philanthropic endeavors.

His past run-ins with the law have also given him some incredible stories to tell, including one police encounter he had as a teenager that was so bad, you can’t help but laugh.

Jelly Roll Went From Jail Cells To Sold-Out Stages

According to the 2023 documentary Jelly Roll: Save Me, the rapper and country artist behind hit songs like “Save Me” and “Wild Ones” had his first run-in with the law when he was only 14 years old. He would spend much of his childhood and early adult years in and out of detention facilities, with police arresting him up to 40 times for various offenses, including aggravated robbery, drug possession, and drug distribution. Unsurprisingly, Jelly Roll spent much of this time in his life assuming he would always be in and out of jail.

“I was charged as an adult years before I could buy a beer, lease an apartment, get a pack of cigarettes. I feel like the justice system at that point kind of parked me on my only set path,” Jelly Roll told Billboard. At only 23 years old, the future superstar had resolved to die in prison or die young on the streets. That is, of course, until a prison guard knocked on his cell door to tell him he had become a father. “I’ve never had nothing in life that urged me in the moment to know that I had to do something different. I have to figure this out right now.”

And figure it out he did. Jelly Roll turned to music as a way to cope and connect with others. This creative passion became a massively successful career, but not before he collected a few wild stories to share later on.

A Police Encounter So Cringey, It’s Almost Funny

During an appearance on the Howard Stern Show, Jelly Roll gave a simple explanation for why police were able to arrest him so many times when he was younger: he couldn’t run very fast. “My successfulness of running from the police is zero and twenty,” he joked. “I was probably 15 years old, and I got arrested once, and I was on a Xanax bar. You know how Xanax makes you a little slow anyways? In my mind, when the police pulled us over, I was like, ‘I’m just going to run.’”

But instead of sprinting through a nearby field like he had hoped, Jelly Roll sort of…fell out of the car in a heap. “The cop was standing there watching me, and 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 laughed.