The rapper-turned-country singer embraces the ‘duality of life’ in his music

Jason Bradley DeFord, better known by his stage name Jelly Roll, grew up in Nashville’s working-class Antioch neighbourhood, just down the road from the Music City’s downtown core. But as a kid in the ’90s, he was more interested in hip-hop than the country music of his hometown.

Now, DeFord is a bonafide country music star, though he started his career as a rap artist.

“I always wanted to be in country music, man,” DeFord tells Q‘s Tom Power. “The joke I tell is that from Antioch to Music Row is 30 minutes, but it took me almost 40 years to get there.”

For many years, DeFord wrote his own rap music and hustled to sell his mixtapes out of the back of his car. But when a production guy heard him singing karaoke, he encouraged DeFord to start singing rather than rapping. DeFord easily found himself making the transition from rap to country.

“Even if you listen to the subject matter of my early hip-hop stuff, I was singing country songs,” he says. “I was just rapping ’em.”

The country music world embraced DeFord much more than the hip-hop world did. Country radio stations played his songs, even though his tattooed face isn’t the classic look of a country musician. Last year, he even won new artist of the year at the 2023 Country Music Association Awards.

I was too rock for hip-hop. I was too hip-hop for country. I was too country for rock.– Jelly Roll

“Country music [gave] me a place to call home, finally,” he says. “No genre would define me. I was too rock for hip-hop. I was too hip-hop for country. I was too country for rock.”

Much of DeFord’s musical output is about the contradictions that lie within each other. Many of his songs discuss mental health and addiction in one line and the power of God in the next. This stems from DeFord’s own experiences with the carceral system, as well as his mother’s struggle with addiction. At 14, he began cycling in and out of prison for various offences, most of which were drug-related charges.

But when DeFord was convicted of a felony at 16, he says it was an “automatic dream killer” that affected everything from international travel to employment to getting home insurance. Still, he knew couldn’t give up on being a musician. After writing songs to express the pain he was feeling inside, he says he finally found purpose for the first time in his life.

His song Halfway to Hell, explores the idea that a person can be both a sinner and a saint at the same time.

“I am the guy that’ll still tear the town up every now and then on a Saturday, but … I’ll show up to church Sunday,” he says. “I think that’s the duality of life.”

DeFord is currently on his first tour in Canada. He stopped at the Royal Ottawa Mental Health Centre for a pop-up show. He ended up spending time with three people on their first day in the detox unit, what DeFord calls the “worst” day of recovery.

Not long after, he went to play another show where a man in the front row held up a sign that said: “Today I celebrate 584 days sober.” It made DeFord tear up and realize his music’s impact on his listeners.

“Maybe I could have been the reason that [the people in the detox unit] end up with 584,” he says. “If I’m just a small part of that, if I’m just the soundtrack to that change.”

Ahead of his forthcoming album, which comes out later this fall, DeFord recently released a new single, I Am Not Okay, about the struggle to wake up and live every day, while still trying to hold on to hope.

“It’s OK to be not OK — and it’s OK to know that you’re going to be alright,” he says. “You can be more than one thing. It’s OK to have two feelings at once.”