Country Superstar Jelly Roll Talks Jailhouse Brawls, Cheap Tattoos, and the Song That Changed His Life

SiriusXM’s Nashville studio was graced by the presence of a hometown hero on Wednesday morning as the award-winning rapper, rocker, and country music sensation Jelly Roll sat down with Howard for his very first Stern Show interview. The 43-year-old singer-songwriter’s epic appearance began with an insightful and unflinchingly candid conversation that covered everything from the Tennessee native’s rough upbringing and former run-ins with the law to his rapid ascent to stardom and well-earned music industry accolades. It concluded with a larger-than-life, three-song concert performance featuring two of Jelly’s massively popular originals and one medley of classic covers.

While talking music with Howard, the artist had plenty to say about his brand-new single, “I Am Not Okay,” and upcoming album as well as the inspiration behind his biggest hits, some of which were penned from lockup. As fans no doubt already know, Jelly famously went to jail over 40 times before putting himself on the straight and narrow.

That left Howard with one burning question for the “Son of a Sinner” singer: “How did you get caught so much?”

“I was the worst criminal ever,” Jelly Roll laughed, adding, “My successfulness of running from the police was zero in 20.”

That didn’t stop him from trying, however, as he explained while recounting a story from his teen years about trying — and failing — to outrun the cops. “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.

After spending so much time behind bars, Jelly admitted he eventually began to feel safer and more comfortable in lockup than out on the streets. Even so, occasional fights were unavoidable. “There’s no getting around physical altercations in jail,” he told Howard, explaining how he once fought his cellmate after spitting in the sink without realizing it was the ultimate sign of disrespect.

The sporadic violence aside, Jelly told Howard jail is filled with dreamers discussing all the great things they planned to do after they got out. For him, the dream was always music. But with no traditional instruments at his disposal, he wrote songs by using his steel bunk bed as a drum. “It had a real hollow sound so you could at least keep your time,” he explained to Howard. “You start kind of humming melodies over this loop … and go from there.”

“The hard part was when you write so many of them, you start to forget the melodies,” the singer 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.”

As much as the music meant to him, he told Howard having a daughter is what ultimately compelled him to clean up his act. “I honestly think if I wouldn’t have had a kid, I never would’ve have broken that cycle.”

Howard imagined that much time in jail might change a person. “Does anything in life scare you after you go through something like that?” he asked.

“My fear now is [for] the people I love,” Jelly said before sharing one recent example of how he worried so much about his daughter’s Sweet 16 party that it gave him an ulcer. “If I lost all this today and moved back to Antioch, I’d be fine,” Jelly concluded. “But if you told me my little girl might not have a friend at her birthday party, I’d cry like a baby before it even happens.”

The Origin of His Nickname

Born Jason DeFord, the musician’s mother nicknamed him Jelly Roll at a very young age.

“If she’d have called me Slim Jim, I might have a six-pack and a big cock,” he told Howard with a laugh.

He wasn’t the only one in his Nashville neighborhood of Antioch with an atypical moniker, either. “Everybody had those horrible nicknames,” the singer laughed. “We had a dude in our neighborhood whose nickname was Shit Stain … He’s a grown man now, he’s 44, and I’m still like, ‘What up, Shit?’”

Howard wondered how Shit Stain was faring these days.

Jelly Roll said he’s no longer in jail. “He did like 16 years,” he explained. “And they called him Shit the whole time.”

Marrying Bunnie Xo and Raising a Family

A drug dealer turned acclaimed musician falling in love with a sex worker turned podcaster isn’t exactly a tale as old as time, but Jelly Roll revealed his relationship with his caring wife Bunnie Xo was as loving as it was unconventional. “We met at a bar. She was in a situation, and I was just so lost in life,” he said, adding, “I loved her from go. I loved her from the moment I met her.”

Howard was grateful Bunnie never got scared off by the singer’s massive rap sheet.

Jelly felt the same way. “She calls me her Pound Puppy,” he laughed, referencing the ‘80s toy. “She adopted a Pound Puppy.” He and Bunnie quietly wed in Las Vegas in 2016 and after a few breakups and shakeups seem to have found their happily ever after. “I think it’s one of the wildest stories that has ever happened in the music business,” Jelly said of their love.

While on the topic of his family, the artist told Howard he works hard to provide his teenage daughter with a more stable home than he had when he was a kid. He’s surrounds her with good role models, too, including country sensations Miranda Lambert, Carrie Underwood, and Lainey Wilson. “I always make it a point to get her around them because all she’s seen [in her life before that] is drug addict women,” Jelly said.

The Song That Changed His Life

Jelly Roll wrote his first No. 1 hit “Save Me” at the height of the pandemic, shortly after the death of his father. “It changed my entire life,” he said, explaining its melody and some of the lyrics came to him in the most unexpected of ways. “It’s the only time in my career this has happened, and I don’t want to sound like a quacko when I say it, but I heard ‘somebody save me’ in a dream to the point I thought I stole it.”

Jelly wrote the song on a Sunday with his friend David Ray, who also played guitar on the track, and by Tuesday they had recorded it, shot the performance video, and uploaded it to his fans. “Forty-eight hours after I wrote this song, it was on my YouTube channel. Seventy-two hours after I wrote this song, it was at a million views,” he said.

“Save Me” was inspired by the classic Bette Midler ballad “The Rose,” a song Jelly Roll’s mother frequently listened to when he was a kid. “She would say, ‘Play this at my funeral,’” he recalled. “She would sit at the kitchen table — I still get emotional listening to it — she would smoke these cigarettes and say, ‘Remember to play this when I die.’”

Howard was heartbroken to hear a mother could say that to her child.

“That’s coming from a woman who didn’t think she was going to live, and I know how that feels, how that feels to think you’re not gonna live,” Jelly said.

Losing Himself Working With Eminem

When Eminem’s manager Paul Rosenberg approached Jelly Roll backstage in 2023, the star was surprised to learn the legendary rapper even knew his name. “’Marshall loves you. We’re going to figure something out — I want to get you all together,’” Jelly recalled Rosenberg saying at the time.

Sure enough, Jelly was enlisted to perform at a special concert for Eminem’s hometown of Detroit — and to sing the hook on the rapper’s 2002 hit, “Sing for the Moment.” “I didn’t meet him until the day we did it … I was so nervous … You could see the nerves on my face,” he recalled of the opportunity to perform on that track. “This song did a lot for me in dark moments of my life … and I’m a lifelong fan.”

Despite the nerves, the experience was an incredible honor. “He’s just such an awesome dude,” Jelly marveled of Eminem. “There are not enough praises for him. He’s inarguably the greatest rapper that ever lived — ever.”

When Jelly Met McCartney

With mainstream success, Jelly Roll has had the opportunity to rub elbows with some of the biggest names in the business. “You find yourself in situations that you never would have dreamed,” he said before noting the friendship he’d forged with Stern Show regular Jon Bon Jovi. “The even weirder part is when it goes past meeting them and you start to develop a relationship with your idols to find out that they’re actually really cool people.”

Perhaps most surreal was his interaction with Sir Paul McCartney. “I lost my mind,” Jelly admitted of meeting the legendary Beatle, who in turn was already aware of the rapper-turned-country star. “He just immediately started loving on me — it was really cool.”

After praising Paul’s songwriting, Jelly Roll spoke to his own success and the added pressure he feels as a songwriter now that he’s become more of a household name. “When cool shit starts happening, you’re like, ‘Man, I don’t want to fuck this off … I’d really like to live this way for the rest of my life if possible,’” he told Howard.

Tattoo U.

Jelly Roll is famously covered head to toe in tattoos, but on Wednesday he told Howard he regrets quite a few of them. Speaking directly to anyone under the age of 25 considering ink, the star wanted to impart some wisdom: don’t be cheap. “We will spend $300 on a pair of fucking shoes … but as soon as a motherfucker wants $400 an hour to tattoo you, we’re out,” he said, adding, “I have a tattoo on my arm that I gave somebody like a quarter sack of bad weed for — and it looks like a quarter sack of bad weed tattoo.”

Jelly also warned of the possibility of infections due to shoddy work —something he knows about firsthand. “I learned nothing,” the “Wild Ones” singer admitted. “I still went back to the same guy that gave me the staph infection.”

Interestingly enough, he’s okay with his face tattoos. “I tried to get one when I was younger, and they wouldn’t do it,” Jelly Roll explained of attempting to go to a certified establishment. “And then I went to jail and got a couple, so when I came out they looked at it like, ‘Well, you’ve already fucked your face up — now we’ll do it.’”

Jelly Roll’s new song “I Am Not Okay” is available now.