‘I’m a broken man putting the puzzle back together’: country star Jelly Roll on prison, addiction and redemption

The singer-songwriter is up for a best new artist Grammy at the age of 38, having broken a cycle of jail time and drug use. He explains his newfound joy – and survivor’s guilt

Whenever Jelly Roll returns from touring, he falls into a depressed state. For a long time he couldn’t figure out why. The rapper turned country singer had written it off as an adrenaline dump; his body getting back to normal after long stretches of wild highs. But recently, he made a breakthrough with his therapist.

“Tour is about the only time that I’ve ever felt valuable in my life,” he says, speaking over Zoom from his home in Nashville, Tennessee. This big man, who spent years of his youth in prison, “felt like I brought no value to any situation; that I’ve only taken away. That I take up too much space.” When he performs he feels as though he’s giving something back. “Now I’m learning to find value when I’m not on stage, because that’s the real test.”

Today, Jelly Roll – his stage name, also that of a dessert, was given to him by his mother on account of him being a pudgy kid – is feeling good, and in demand. After eight hours of media commitments, he’ll fly to San Antonio to perform before flying to California for another show. “That’ll be my day, yes sir. It’s a great time to be alive, baby.”

You can see why. Earlier this month Jelly Roll – real name Jason DeFord – won the Country Music award for best new artist, and was nominated in four other categories. It was the peak of an already successful year on the awards trail: he had already bagged three CMT Music awards. Then, two days later, he was nominated for two Grammys, including in the prestigious category of best new artist. Aged 38 and after more than a dozen albums across different genres, he’s only now finding mainstream recognition. “There’s something that’s kind of brokenly beautiful about this almost 40-year-old man making his way, you know,” he says. “I’m the real Cinderella man.”

You can split DeFord’s career neatly in two at the release of his 2020 single Save Me. Before: the rapper who spent 15 years handing out mixtapes, self-promoting albums, taking any gig that paid. After: the bona fide tattooed, gold-toothed country star, who is now the new face of the genre, according to one recent interview. As he puts it, “the man changed and the music followed it”.

In both stages of his career, though, DeFord has always spoken candidly about his struggles and his need for redemption. He has suffered from drug addiction, been diagnosed with severe depression, has low self-esteem, and is plagued with insecurity. For a long time he had impostor syndrome, since replaced by fears of ephemeral success. In his own words, he’s been a loser, a stealer, a lost cause whose past still haunts him. His most recent album, Whitsitt Chapel, is a raw, aching distillation of all this hopelessness and torment.

“I see myself as a broken man that’s trying to put the pieces of the puzzle back together,” he says. “I looked at the whole experience as a cry for help. And it was heard. The music represents so many people that haven’t felt heard.”

DeFord’s ascension is the latest to suggest country music is broadening. But while the genre may be diversifying in terms of its sound and (to some extent) the artists themselves, in other areas it’s hardening. In a recent LA Times interview Maren Morris said that she had to step back from the genre owing to what she perceives as endemic industry racism and misogyny.

It’s a friction DeFord is aware of, but he doesn’t “do the politics stuff … I miss when politics didn’t get involved. I hate that we’re so tribal. Tribalism is higher than it’s ever been in America right now. When we’re down to politics being our last way to find a way to connect with people, we’re in trouble. This thing is going to hell in a handbasket.”

But is there still room for progressive music in the country space? “Yeah, for sure, man.” He cites Tyler Childers and Sturgill Simpson as two stars who have also been outspoken on liberal causes. “Maren Morris jumped off a winning horse. Bottom line. Period. You know what I mean? Country music’s never been bigger and better than it is right now. It’s never been more diverse.”

DeFord grew up in Antioch, Tennessee, a blue-collar suburb of Nashville he has described as “Anytown, USA”. His father was a meat salesman with a side hustle as a bookie, while his mother struggled with mental health issues and a drug addiction that started with pain medications. Through his childhood DeFord never felt comfortable: at school he was made fun of for his size, his clothes and his background. He found some worth in music, rapping in middle school and gathering crowds. But he knew no one around him that “actually had a career. I love when artists are like, ‘I dreamed about this since I was five.’ It’s like, nah, I didn’t. I didn’t think I was gonna make it out of being incarcerated most of my life.”

At 13 he spent time in a juvenile facility after being caught with weed. By 15, he says, he had tried most drugs: pills cocaine, acid, mushrooms, meth. At 16, he was charged as an adult for an aggravated assault case after attempting to steal weed from someone while armed and landed himself an 18-month sentence. For a decade he drifted in and out of prison. Offences included violating probation, failing drug tests and possession of crack with intent to resell.

His music was still there, on mixtapes that he handed out with the cocaine he sold, but life felt hopeless, so more time inside was hardly a deterrent. “Jail was like a high school reunion for me. You go in there, it’s like, ‘Oh, you’re still here, what’s up dude’,” he says. “The rotating door of the judicial system, it’s rough, man.”

In 2008, when DeFord was 23 and sitting in his cell, a guard told him he now had a baby girl (her mother was an ex-partner from a short-lived relationship). It was the motivation he needed to turn his life around. He had two plans. One was to study for his General Educational Diploma (he passed first time), become a social worker and do “whatever it took not to go to jail or get shot and killed”. The other was music.

At 25 he left prison for the last time and, without any studio help, built a sizeable fanbase. “I had a billion views on my YouTube channel before I signed a record deal,” he claims.

But initially, the music establishment didn’t want to know. He was too rock for country, too country for rap, too rap for rock. Record labels told him he was not a relatable figure, pointing to his obesity, tattoos and criminal record. “[I was told] nobody’s gonna buy a 400-pound man singing sad songs. Like, it’s just not in the bingo card for what the climate of music is.”

The tipping point came in 2020 with Save Me, his unvarnished cry for help with addiction. YouTube views rolled in, eventually in their hundreds of millions, and record labels started calling. Since then he has had two successful albums, Ballads of the Broken and Whitsitt Chapel.

Earlier this year DeFord released a documentary with ABC, Jelly Roll: Save Me, profiling his redemption arc. Most notable is his relationship with fans, young offenders and recovering addicts, who tell him how his music saved them or helped them grieve. He seems to feel every word. Jelly Roll gigs have been compared to church revivals and 12-step programmes. People hold up signs naming loved ones lost to addiction. He says he cries almost every night he’s on stage, usually when it comes to the part where he celebrates those in the audience in recovery, or who are there on behalf of people they love. He is almost in tears just talking about this.

Does it ever take its toll on him? “I don’t look at that as bad at all, man,” he says. “God gave me a platform to be useful and of service to people.” Why does he think people respond to him so viscerally? “It’s sad to say this, but there’s just not a lot of people that write the kind of songs I’m willing to write and talk about the topics I’m willing to talk about, but yet they’re so common.”

When DeFord sold out his gig at Nashville’s Bridgestone Arena, he donated the profits (an estimated $400,000) to a local nonprofit charity for at-risk kids and built a recording studio inside a youth centre. “When I was a kid, I feel like they focused on discipline and not rehabilitation, and dude, when you’re 16 years old, I don’t care what crime you committed, you don’t need to put your nose in the corner. You need a hug. You need somebody to tell you they love you.”

DeFord is still feeling the impact of his own conviction; as a result of his felony conviction for robbery he still can’t vote, own a firearm or volunteer at most charities. Travel is complicated, too; he recently had to cancel a show in London. He has been in touch with the governor of Tennessee and while a pardon would change his life, his eyes are set on broader criminal justice reform. “I just want to be a part of the solution, because I saw what the problem was for sure.”

DeFord desperately wants action on the US fentanyl crisis, too. “Fifteen people an hour die in the United States of America right now.” He knows at least 30 people who have died. When he thinks about his own friends still struggling with addiction, he’s overcome with survivor’s guilt. “I have a phone full of the sob stories; guys I knew from the past. And they want two grand, five grand, a car, a house.” He laughs at the notion that people think he is in a position where he can just hand out houses. “So you read them. And it just hurts. The guilt you feel creates a spiral of shame. But it also hurts to separate yourself from these people.”

Some of his attempts to help have been stymied by a completely overwhelmed rehabilitation system. “I tried to pay for a guy to go to rehab recently and we called every rehab in America. The best one that we could find – with the resources even I have – had a two-week wait before you could get in. Like, what is he supposed to do for two weeks? Die? I can’t get him off of it – he’ll die right here on the floor.”

Today, DeFord still smokes weed and drinks, but has cut out the drugs he knew would kill him. “I walk the line when I talk about my recovery out of respect for the people that have actually worked the programme and completely sobered up,” he says. “I had to get rid of the lean [codeine-laced drink], the pills, the cocaine. I didn’t have a choice. It was me or them, and I had to learn to love myself.”

He lives with his wife, Bunnie DeFord, AKA Bunnie XO, a former sex worker from the west coast who now hosts the popular Dumb Blonde podcast, and his 15-year-old daughter, Bailee (from a previous relationship). (He also has one son born in 2016 from another previous relationship who lives with his mother.) He finally feels he belongs and has purpose. “I feel I’ve never felt more heard or seen or more appreciated and more loved than I have the last year,” he says. “The biggest thing is, I know in my heart, I changed. That’s what I know – I’m not who I was.”

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