Jelly Roll on His Triumphant Journey from Drug Dealer to Arena Headliner: ‘You Couldn’t Write a Cinderella Story Cooler Than This’

What a difference a year makes. In 2021, Jelly Roll played a sold-out show to just over 2,300 fans at Nashville’s revered Ryman Auditorium. This Friday (Dec. 9), the Stoney Creek Records/BMG artist is headlining the nearly 19,000-capacity Bridgestone Arena.

The moment will prove a triumphant homecoming for an artist (real name: Jason DeFord) who has gone from selling mixtapes out of his car in his hometown of Nashville suburb Antioch, and releasing over a dozen independent albums, to becoming a genre-fluid hitmaker with a No. 1 on Billboard’s Mainstream Rock Airplay chart (“Dead Man Walking”) and a Top 10 (and rising) on the Country Airplay chart (“Son of a Sinner”). While the venue’s seats will be filled with fans, backstage will be just as packed with friends and family that have supported the 37-year-old singer-songwriter for years.

“It’s so bad,” he tells Billboard with a laugh, acknowledging it’s a great problem to have. “I went to Bridgestone today with the relations manager that deals with backstage stuff, hospitality, just to look at all the dressing rooms and everywhere we can possibly put people… just to f–king figure it out how we’re gonna do this. But it’s incredible. You couldn’t write a Cinderella story cooler than this, saying that I’ll have a headlining show at Bridgestone while I have a top 10 at country radio. I look at it like it’s my introduction party to Nashville, even though I was born here.”

He promises some high-profile special guests and several surprises in the set list.

“We’ve got something for everyone. If you’re a Nashville guy who remembers when I was putting out mix tapes, I have something that will blow your mind. If you’ve just heard ‘Son of a Sinner,’ it’s gonna be great,” he says.

Jelly Roll has logged 16 weeks atop Billboard’s Emerging Artists chart — where he still sits — marking the second-longest reign on the chart, behind only NLE Choppa’s 24-week streak at the pinnacle. He hopes his success, like his music, serves as inspiration to those who are struggling.

“I think what I think I represent is just a beacon of hope,” he says. “I don’t look like the guy that you would’ve assumed would’ve made it [in the music industry]. Sam Hunt’s a really dear friend of mine, and Sam is just a big striking, handsome guy. When you see him, you’re like, ‘Oh, I get it.’ When you see me, you don’t get it initially — then you meet me, and hear the story and hear the music. I just feel like I represent the guy who looks at himself in the mirror every day and goes, ‘Yeah, guys like me don’t make it.’”

Not only will the show be his largest headlining show to date, but it will aid a good cause — one that is intensely personal for the former addict and drug dealer. Proceeds from the show will benefit the local non-profit Impact Youth Outreach, which serves at-risk, disadvantaged youth in the Nashville area. He is also donating $250,000 to Impact Youth Outreach, and plans to build a recording studio and music programs at the Davidson County Juvenile Detention Center. With Impact Youth Outreach, he is also funding Hometown Heroes Scholarships for Metro Nashville Public School seniors.

Prior to launching his music career, Jelly Roll had been in and out of the juvenile detention center since age 14. (“I spent 14-24 in trouble,” he notes.) He spoke with Billboard just before returning to the center to speak with youth in the same pod he had once been housed in.

“[It’s] where I spent the worst 18 months of my life, but it was a turning point,” he says, noting it was where he began rapping and where he had his first rap battle. “I found my real love for rapping here. I loved all music as a listener, but I didn’t think I could sing, but there was something about rhythmic rapping and poetry that I understood… there was a lot of hip-hop, but we didn’t get radios or nothing. A lot of what we heard was just rapping to each other, and that got me involved in the art form, because it was our only source of entertainment. Adult jails at least get headphones.”

“I’m passionate about this,” he says of helping people overcome their issues. “It’s not even scratching the surface of the 10-year plan we have for at-risk youth and people dealing with drug addictions in this town. I came up here on Thanksgiving Day and fed a bunch of kids. I sat with them and listened to their stories. There were kids who had been here 18 months, 20 months already. How critical an amount of time that is when you’re 15.”

He’s working with Impact Youth Outreach president Robert C. Sherill, whom Jelly Roll met over two decades ago, and who followed a parallel path to Jelly Roll’s own journey. Sherill previously spent time at a federal penitentiary before becoming a successful Nashville entrepreneur, launching a commercial cleaning company Imperial Cleaning Systems.

“This town used to be tiny. The big drug dealer in North Nashville knew the big drug dealer in South Nashville. I was in my late teens before I met a successful adult that didn’t sell drugs,” Jelly Roll says. “[Sherrill and I] met when we were kind of on our s–t, and we got through our s–t around the same time — I chased the creative arts and he traced entrepreneurship, and wanted to give back to the youth. It’s a beautiful connection — and we look cool together. It’s a skinny, really fit Black dude that hardly drinks and an overweight, fat white guy that drinks a lot. We’re kind of a TV show.”

When he takes the stage Friday at Bridgestone, Jelly Roll will perform his newest release, “She,” another unflinching look at an aspect of addiction — this time from the viewpoint of someone watching as a loved one struggles.

“I think we all know a ‘She.’ And for me, just being honest, ‘She’ was my child’s mother. And ‘She’ was my mother. I just hope someone hears this, or someone’s family member sends them this song and we can help create some change. I meet fans that tell me a lot of stories — my music helped them through addiction, or to decide not to commit suicide. I want to keep making music that helps people. That makes it worth it.”