Jelly Roll's Most Tragic Memories From His Time In Prison

Jelly Roll (who was born Jason DeFord) was incarcerated, on and off, for more than 10 years. The first time he was arrested, he was only 14. He went on to serve time for different crimes, including aggravated robbery and drug dealing. At 16, he was charged as an adult. "I won't even talk about the crimes because I don't think there's no glory in them and I'm not proud of them," he said on the "Bobby Bones Show." The memories he has from that time are enough to fill a book — or several albums. 

But most of them are unpleasant. From writing songs with no musical instruments to attempting to cook with prison food, most of Jelly Roll's time in jail was filled with examples of resilience and survival. But it was also in prison that he received his biggest blessing. The Grammy-nominated singer-songwriter became a father while behind bars, which was bittersweet. On the one hand, he wasn't there for the early months. On the other, his daughter became his saving grace. Thanks to her, he was able to break the cycle. 

He knows he made a serious mistake that had led to consequences, but he disagrees with how the justice system currently works. "They were talking about giving me more time than I'd been alive," he told Billboard in 2023. While he doesn't have fond memories of jail, Jelly Roll keeps them alive so he can be an advocate for those in a similar situation.

Jelly Roll couldn't see his newborn daughter because he was incarcerated

After 12 years in and out of jail, Jelly Roll's prospects of leaving the system seemed improbable. While stuck in what he called "the revolving door of the judicial system," for every couple of years he served in jail, he spent a few months at home, per the "Bobby Bones Show." During one of those stints of freedom, Jelly Roll got a woman pregnant. He was aware of the pregnancy, but he certainly didn't expect it would mean redemption.

On May 22, 2008, a guard knocked on cell 223 at the Metro-Davidson County Detention Facility in Nashville to inform Jelly Roll his daughter had been born. "I had a Damascus Road experience," he said on the "Bobby Bones Show" in May 2022, referring to the moment Paul converted to Christianity upon encountering a resurrected Jesus. Jelly Roll had a tumultuous childhood growing up with a mother who suffered from mental-health issues and addiction.

But he had a present father who helped bring stability to his environment. That was the role model he wanted to emulate. "I had a good father," he said on the "Bobby Bones Show." He went on, "He was a hustler, but he was a really good man. And I was like, 'I want to be a good father.'" In 2017, Jelly Roll and his wife Bunnie Xo got custody of his daughter Bailee Ann as her mother struggled with addiction — a decision that changed the girl's life for the better. 

Jelly Roll still felt safer in prison than in his community

After spending his youth more in the system than out of it, Jelly Roll began to feel more comfortable in prison than at home. "There's a sense of safety there," he said on "The Howard Stern Show" in June 2024. "When you were in the streets, there was no safety. Anything could happen at any time." On the outside, things were more murky. "Rule number one of the streets are there are no rules. Rule number two is, don't forget number one," he said.

Being in jail also meant Jelly Roll didn't have to figure out his life — at least not yet. It gave him a false sense of productive procrastination. "In jail was this little bit of comfort and chance to regroup and you'd always sell yourself the dream in jail, too. 'Oh, I'm gonna figure this out. I'm changing. I got an idea,'" he said. Jelly Roll did have ideas. He wrote them down as lyrics. But he lacked the motivation to turn his songwriting skills into something productive.

That changed when Jelly Roll's daughter Bailee Ann was born. At that moment, he had no more time to kill. He wanted to be a good dad so he left the system for good and got to work as a musician, though the journey was far from easy. "It was 10 years of sleeping in a van and selling mix tapes out of my trunk," he said on "Jimmy Kimmel Live."

Jelly Roll couldn't avoid prison fights

Jelly Roll had to learn lots of new rules when he first arrived in adult jail. He learned one of them the hard way. "The tolerance of respect in jail is so different than the tolerance of respect everywhere else in life," he said in the "Howard Stern Show" interview. What might be considered mundane outside might be taken as a profound disrespect behind bars. The first fight he was in happened because he spat in his cell sink. But he learned it wasn't personal.

The sink isn't just a sink in a cell. For his cellmate, it served many purposes. "The way he looked at the sink was, 'I can put ice in this sink, I can put drinks in this sink, I can mix drinks in this sink, I can heat stuff up in this sink, I can put hot water in this sink and smoosh up honey buns in this sink,'" he explained. Jelly Roll quickly learned fights are the way inmates establish boundaries. "There's no getting around a physical altercation in jail," he said.

But just because that's how inmates handle their issues in jail doesn't mean Jelly Roll believes it should be the same anywhere else. When a fight broke out at his September 2023 concert in Denver, Colorado, he promptly addressed it. "You don't f***ing fight at no f***ing Jelly Roll show. This is a family affair," he said (via TikTok).

Prison foods brings up bad memories for Jelly Roll

Jelly Roll became a master in crafting tasty snacks using what was available. One of his favorites was the so-called ghetto dough. It consisted of crunched-up Flamin' Hot Cheetos mixed with cut-up beef sticks, cheese, and enough water to make a patty to be eaten with crackers. "It's actually really good!" he said on the "Taste of Nights, On Demand" podcast. Another all-time favorite was a cake made with two Grandma cookies filled with Moon Pie and Snickers before going in the microwave.

But don't expect to see those options on Jelly Roll's menu at home. "I just don't make them ... I won't do it. I think that stuff's bad luck," he said. "I believe what's in jail stays in jail." He did make an exception for Bunnie Xo, however. For one of her YouTube channel's episodes posted in April 2020, Jelly Roll's wife asked her followers to send in their favorite prison foods and prison hacks in general. Halfway through, Jelly Roll joined her to show off his skills.

Instead of the Flamin' Hot flavor, Jelly Roll encountered regular Cheetos. "Daddy, I hate Flamin' Hot Cheetos," Bunnie responded to his protests. Her choice of crackers also missed the mark. "We don't get those in jail ... This is not a real prison hack, y'all. This is Bunnie's version of it. This is the bougie prison hack," he said. At least it came out looking good!

Jelly Roll spent the bulk of his time in prison writing songs without instruments

Jelly Roll started writing music way before he started getting in trouble with the law. Even as he dealt drugs, he tried to promote his music. "I'm just like, 'Yo, here's a sack of weed. Here's a gram of coke. Here's a mixtape,'" he told CBS This Morning in January 2024, when he visited his old cell. That didn't change while in jail. Jelly Roll reminisced over the small metal table that helped him craft some of the songs that made him an acclaimed artist a decade later.

"I wrote hundreds of songs right here," he said, getting emotional. "I wrote 'Riding' All Alone”s chorus right here." But what he wrote behind bars was a lot different from what fans hear today. Roll had no access to instruments, so he used the table or his bunk's frame to keep the time. "You start kind of humming melodies over this loop, over this kind of a track in your head," he explained on "The Howard Stern Show." 

In his "Jimmy Kimmel Live" interview, Jelly Roll demonstrated the process, banging his fist while snapping his fingers to mark the time as he came up with lyrics on the spot. While impressive, the process was far from perfect. After a while, he started to forget the melodies. "I ended up coming home with a bunch of songs that I couldn't remember the melodies to," he told Stern. "But I had really good lyrics."