Jelly Roll Recalls Unsuccessful Runs-Ins With The Law On ‘Howard Stern’: ‘I Was The Worst Criminal Ever’

Jelly Roll’s appearance on The Howard Stern Show prompted stories from his teenage years behind bars.


Madeleine O’Connell

| Posted on

June 14, 2024


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Jelly Roll visits SiriusXM Studios on June 12, 2024 in New York City ; Photo by Jason Kempin/Getty Images for SiriusXM

Jelly Roll certainly had his fair share of run-ins with the law before becoming a record-breaking country music superstar. During his recent appearance on SiriusXM’s The Howard Stern Show, Jelly Roll admitted that his drug dealing days certainly did not prove to be successful as he was busted at least 47 times. 

“How did you get caught so much?” Stern asked, to which the multi-genre phenomenon replied, “I was the worst criminal ever,” he said with a laugh. “My successfulness of running from the police was zero in 20.”

Jelly Roll Recounts A Failed Running Attempt

While sharing a story from his teenage years, Jelly Roll recalls feeling confident in his abilities to get away. Even with the knowledge that he likely wouldn’t be successful, he still found himself attempting to outrun the police.

“In my mind, I jumped out [of the car] and sprinted across the field and almost made it,” Jelly recalled. “[But] I was so fat and Xanax-ed out I stood out and got two steps. The cop was standing there, watching me, and I fell, and he just laid on top of me.”

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

Writing Music While Behind Bars

Jelly Roll performs at Nissan Stadium on Saturday, June 8 during CMA Fest 2024 in downtown Nashville; Photo by Hunter Berry, CMA
Jelly Roll performs at Nissan Stadium on Saturday, June 8 during CMA Fest 2024 in downtown Nashville; Photo by Hunter Berry, CMA

With his many failed attempts Jelly Roll had plenty of time behind bars to dream about the music career he might one day have. The genre-bending singer didn’t have the luxury of traditional instruments or recording devices while inside the cell, but he made do with what he had, including his steel bunk bed which acted as a great alternative for a drum. 

“It had a real hollow sound so you could at least keep your time,” he explained to Stern. “You start kind of humming melodies over this loop … and go from there.”

He began piling up songs that he took home after serving his time and while the lyrics stayed with him, the melodies were unfortunately often lost. 

“The hard part was when you write so many of them, you start to forget the melodies,” he continued. “I ended up coming home with a bunch of songs that I didn’t have the melodies to, but I had really good lyrics.”

Performed Brand-New Single, “I Am Not Okay”

Jelly Roll; I Am Not Okay
Jelly Roll; I Am Not Okay

Along with discussing his rough upbringing and his chapter behind bars, Jelly Roll’s first experience on The Howard Stern Show also included a live performance of his brand-new single, “I Am Not Okay.”

Fans first got to see this song come to life when Jelly Roll debuted it on the Season 25 finale of The Voice. The song officially dropped on Wednesday, June 12, via BBR Music Group/BMG in partnership with Republic Records and serves as Jelly Rolls first official release since his record-breaking debut Country album, Whitsitt Chapel, which was unveiled last June. 

The Meaning Behind The Raw Lyrics

Listeners now have the chance to take in all the emotions and sincerity that is embedded within the tune as the Tennessee native sings about holding onto hope for the future, even in his darkest days. His gritty vocals offer true vulnerability behind each lyric that mirrors his real-life journey. 

Jelly Roll sings, “I am not okay/ I’m barely gettin’ by/ I’m losin’ track of days/ And losin’ sleep at night/ I am not okay/ I’m hangin’ on the rails/ So if I say I’m fine/ Just know I’ve learned to hide it well.”

The just-released track is also expected to appear on Jelly Roll’s forthcoming new album, due out later this year. 

YouTube video

Earlier this week, he snagged his fifth consecutive No. 1 with “Halfway To Hell.” The fan-favorite track officially impacted airwaves on January 22, 2024, and was named most-added upon its debut, earning an impressive 92 first-week adds on stations around the country. 

Beginning this August, fans can catch Jelly Roll performing on his headlining Beautifully Broken Tour. He is scheduled to make stops in Salt Lake City, New Orleans, Charleston, Boston, New York and many other cities through October.  

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Madeleine O’Connell graduated from North Central College with a bachelors degree in Journalism and Broadcast Communications before deciding to pursue her studies further at DePaul University. There, she earned her masters degree in Digital Communication & Media Arts. O’Connell served as a freelance writer for over two years while also interning with the Academy of Country Music, SiriusXM and Circle Media and assisting with Amazon Music’s Country Heat Weekly podcast. In addition to Country Now, she has been published in American Songwriter, Music Mayhem, and Holler.Country. Madeleine O’Connell is a member of the Country Music Association and the Academy of Country Music.