The Rise of Jelly Roll: How a Tattooed Ex-Con and Former Rapper Became One of Country Music’s Biggest Stars

It’s an unlikely success story, but it’s the kind country music loves to tell.

The name Jelly Roll only became a household name over the last few years, but almost anyone can empathize with his struggles. After a troubled childhood and multiple incarcerations as a teen, the Tennessee native got motivated to better himself and follow his dreams — and that led him to stardom.

At the 2023 CMT Music Awards this year, Jelly won Male Video of the Year, Male Breakthrough Video of the Year, and Digital-First Performance of the Year, for his breakout song, “Son of a Sinner.” At Wednesday’s 2023 CMA Awards, he was nominated five times, scoring a win for New Artist of the Year. And he’s a favorite for several nominations at the 2024 GRAMMY Awards, which will be announced on Friday.

“It was the nod of approval I prayed for,” Jelly Roll told ET of his CMA nominations — which are voted on by his country music peers. “I knew that we were selling tickets, I knew that fans were with us, I knew that we had people that were getting moved by the music, but I wasn’t really sure what Nashville thought of me, you know?”

Here’s a look back at the winding road that led Jelly Roll from teenage delinquent to country music star.

EARLY STRUGGLES

Born Jason Bradley DeFord in Nashville in 1982, a tumultuous upbringing led Jelly Roll to an early life of crime that landed him in jail before he could even graduate high school. He was first imprisoned at age 14, and welcomed his first child while still behind bars.

“A guard knocks on my cell door midafternoon during lockdown,” Jelly recalled in an interview with Billboard earlier this year. “He goes, ‘You had a kid today.’ 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.” 

The birth of his daughter, Bailee, in 2008 forced things into perspective for the singer, who decided to pursue his GED in an attempt to better himself.

“I spent less than 60 to 70 days in high school. I thought I was a real dumbass. I thought I was learning disabled,” he said, revealing that he passed his exam on the first try. “I walked in there and smacked that b**ch out of the park.”

He first tried his hand at the music business in 2003, though he started out in hip-hop with his first release, The Plain Shmear Tape. A string of collaborations, mixtapes and further incarcerations followed, until Jelly made the pivot to rock and country music, ultimately landing himself on the Grand Old Opry stage in November 2021.

“I cried like a baby in front of 12 strangers. I had just signed my record deal, so I didn’t even really know my record label,” he recalled of the moment ahead of his fourth performance in April 2023. “But it was part of the reason I signed my record deal – I had two prerequisites in my deal. I was like ‘You gotta promise me you’ll get me in the local newspaper, then you gotta promise me you’ll get me to the Grand Ole Opry.’ I had to at least prove that I am who I say I am, even if they never bring me back, that’s fine. But just let me be the guy who gets to do it.”

RISE TO SUCCESS

Jelly’s first major label album, 2021’s Ballad of the Broken, landed him on both the rock and country charts, but it was one of the album’s only truly country tracks, “Son of a Sinner,” that put him on the map. Released as a single in March 2022, the song hit No. 1 on Billboard’s US Country Airplay chart, and inspired the singer to move even further toward the country sound for his 2023 follow-up, Whitsitt Chapel.

So far, the album has spawned two hit singles on the country charts, “Need a Favor” and “Save Me,” the latter of which features another major country star of the moment, Lainey Wilson.

And it’s no surprise that the duo was the most nominated artists at this year’s CMA Awards. Wilson was the top nominee of the night, with nine nods, while Jelly was the top-nominated male artist, with five.

“Dude, I don’t think I even woke up expecting a nomination, so when they told me I was the most-nominated male, I almost pooped myself,” he joked to ET during rehearsals for the show at Bridgestone Arena this week. 

In all seriousness, Jelly admitted that the recognition from country music peers was a major moment for him and his career.

“It was the nod of approval I prayed for,” he shared. “I knew that we were selling tickets, I knew that fans were with us, I knew that we had people that were getting moved by the music, but I wasn’t really sure what Nashville thought of me, you know?”

“It makes me want to get emotional,” he added. “I’m really getting teary-eyed. For me, it was really like, you know, I’m welcome here and it was really cool.” 

But the journey’s just beginning for Jelly — and he’s already made some majorly famous friends along the way, like Dwayne Johnson!

“I’m not making this up. The Rock was listening to Jelly Roll music when Spotify numbers said only 30,000 people were listening to Jelly Roll,” the musician told ET back in June. “He’s really been with me from the beginning. I don’t share what that story is, but he has a story that the music was there for him at a moment when he needed it. And that was awesome to hear from him.”

“This is … seven, eight years ago even and we’ve kept in touch,” he continued. “He was the first person to congratulate me on my Grand Ole Opry debut; first person to congratulate [me], and when I played at the Ryman [Auditorium]. The first DM I got when I announced [the historic] Bridgestone [Arena show in 2022]. I mean, these pinnacles in my career. He’s always the first person in my messages.”

FAMILY FIRST

Along with his professional success, the singer’s family life is improving as well. Today, Jelly has full custody of Bailee and is raising her along with his wife, Bunnie, whom he married in 2016. That’s the same year that he welcomed his second child, son Noah, with a former girlfriend. 

Calling Bunnie “a beacon of change in my life” in his Billboard interview, Jelly credited her with helping him to gain custody of Bailee. 

“You’re talking about a woman that came in and took a child that was soon to be born and a child that [we were] soon to have full custody of,” he said of his wife, who is a former sex worker and current podcast host. “I would have never got custody of my daughter without her. I wouldn’t have had the stability or the money.” 

Speaking to his new fortune, Jelly also revealed the surprising first splurge he made after hitting it big financially: therapy for both himself and his daughter.

“Her father was in jail when she was born. Her mother ended up hooked on heroin and disappeared,” he continued. “I’m watching the cycle still continue. That’s another reason it’s so easy to draw inspiration from my songs: I’m still watching it in real time.”

THE FUTURE IS BRIGHT

As he continues to work on himself, there’s plenty of people in the music industry that want to work with him. He was reaching out to Post Malone and Zach Bryan at the 2023 CMA Awards this week, and said his inclusion and recognition at the awards show proved how the doors to the country music scene are more open than ever.

“Country music is on fire,” Jelly Roll gushed to ET ahead of the awards show. “The spectrum of country music and the net of country music is wider than it’s ever been. More people are singing it and singing it different than they ever sang it. More people are watching it than have ever watched it. Country music is the new pop.” 

Even after winning New Artist of the Year, however, Jelly was still struggling to believe the honor his peers had bestowed him.

“I didn’t think I had a chance, man,” he told ET backstage after the win — and his viral acceptance speech. “It was wasn’t even in my mind, to be honest.”

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