From Prison to No. 1: Nashville Rising Star Jelly Roll Proves That ‘Losers Can Win’

Jelly Roll will perform at Billboard‘s inaugural Billboard Country Live in Concert event in Nashville on June 6.

In January 1999, one month after he turned 14, Jason DeFord was baptized by full immersion at Whitsitt Chapel Baptist Church in Antioch, Tenn. By the end of that year, he was incarcerated for the first, but not the last, time. For the next decade, DeFord cycled in and out of juvenile and then adult correctional facilities for crimes ranging from aggravated robbery to drug dealing.

“I got baptized in here some 20 years ago and have since done nothing but go to prison, treat a bunch of people wrong, make a lot of mistakes in life, turn it around, [then] go on to be a f–king multimillionaire and help as many people as I possibly can,” says DeFord today, a hint of awe in his voice as he sits in a red upholstered pew at Whitsitt Chapel. The 38-year-old — now better known as the inspirational, tattoo-covered artist Jelly Roll — recently returned to the church for the first time in decades. “It’s the f–king wildest story ever to me — maybe because I’m the one f–king in the middle of it — but that sh-t’s crazy.”

Jelly (whose mother christened him with the nickname when he was little) has risen from the streets of Antioch to the upper reaches of Billboard’s rap, rock and now country charts, and even played the revered Grand Ole Opry. But he still struggles to reconcile that hopeless past with his prosperous present and seemingly limitless future. On the gut-wrenchingly raw Whitsitt Chapel, out June 2 on Bailee & Buddy/Stoney Creek Records/BMG, Jelly relives his search for refuge and redemption in a world where sinners outnumber saints and hell often feels closer than heaven. As he sings on “Save Me”: “I’m a lost cause/Baby don’t waste your time on me/I’m so damaged beyond repair/Life has shattered my hopes and dreams.”

“That’s what country is, anyway, right? Three chords and the solid truth,” says Jelly, paraphrasing legendary songwriter Howard Harlan’s oft-quoted description of a good country song.

Much of Jelly’s own truth is written in ink on his face. There’s a heart with a lock, a rose, three crosses and a tear drop. There’s his 7-year-old son Noah’s name. His hair has grown over his 15-year-old daughter Bailee’s name, but it’s there, too. On his left cheek, there’s an apple core, an homage to some of his die-hard fans who call themselves the Bad Apples. Emblazoned across his forehead, Jelly’s latest tattoo describes who he is now: “Music Man.”

Music was his way out — it just took him decades to get here. He wrote his first rap when he was 9 or 10, and by the time he was in eighth grade, he was passing out mixtapes of his music in the high school parking lot. “There was a place in Antioch that would let us cut demos for like 30 bucks an hour,” he says. “We had a dude who had a rolling keyboard and he’d make beats.”

But his love of music couldn’t keep him out of trouble. Everyone around him had a hustle — even his father, who ran a wholesale meat business, was a bookie on the side — and he wanted one of his own. “As f–ked up as this may sound, there were drug dealers and drug users,” he says. “I wanted to be the guy getting money, not the guy losing it.”

Jelly has three older half-siblings, but he’s the only child from his parents’ union, which he says was his father’s fifth or sixth. His parents divorced when he was 13, and Jelly felt responsible for his mother, who suffered from mental health and substance abuse issues. “I told my dad before he died [in 2019], ‘I wonder, if I’d have moved in with you when you divorced, if I’d have went to Vanderbilt [University] or something.’ But I felt this need to take care of my mother back then. I think that’s what really did it, too,” he adds, in terms of why he turned to crime. “When he left, I was like, ‘Somebody’s got to do what he was doing, at least trying to figure out some money.’ ”

Still, he never abandoned music entirely. Customers who bought quarter ounces of cocaine also got a free mixtape of his raps. “I always knew that the music was my only chance because I knew [from] the way that people in the community responded to it that it could be big,” he says.

Jelly says when he was 16, he was arrested for aggravated robbery and charged as an adult. “I never want to overlook the fact that it was a heinous crime,” he says, his voice still filled with remorse. “This is a grown man looking back at a 16-year-old kid that made the worst decision that he could have made in life and people could have got hurt and, by the grace of God, thankfully, nobody did.”

But he’s also bitter that at such a young age the judicial system offered him little chance at rehabilitation. “They were talking about giving me more time than I’d been alive,” he says of a potential 20-year sentence. (He ultimately served over a year for the charge, followed by more than seven years’ probation.) “I hadn’t hit my last growth spurt. I was charged as an adult years before I could buy a beer, lease an apartment, get a pack of cigarettes … I feel like the justice system at that point kind of parked me on my only set path.”

Tennessee has a zero-tolerance policy for ­violent offenders, so that one charge is still on his record — and has very real repercussions. Jelly, an avid golfer, tried to buy a house in a community with its own course not long ago and was rejected. “Imagine changing your life in such a way that you can afford the kind of house in this community I was looking at,” he says. “My money was welcome, but I wasn’t, all because of something I did [almost] 24 years ago.”

Jelly can’t vote, or volunteer at most nonprofits, or own a firearm. Until recently, he couldn’t get a passport, which limited his ability to tour abroad. “The trick is when America finally says, ‘We’ll let you leave,’ the amount of countries that won’t let you come in … We had to cancel my London debut show.”

That cancellation is one of the few roadblocks that Jelly has faced recently. But after years of struggling, he’s finally knocking down the doors that once seemed closed. He’s writing with Miranda Lambert and Ashley McBryde, the latter of whom will open for him in select cities on his 44-date North American arena tour later this summer. Drake responds to his Instagram posts, and Garth Brooks, the artist he has seen most in concert, greeted him with a massive bear hug when they met in May at the Academy of Country Music Awards. In May 2022, he topped Billboard’s Mainstream Rock Airplay chart with “Dead Man Walking,” only to reach the summit of the Country Airplay chart seven months later with “Son of a Sinner.” Starting in 2022, he spent a record-setting 28 weeks at No. 1 on the Emerging Artists chart, which ranks the most popular developing acts in all genres.

But a difficult truth follows him: As he sings on “Unlive,” a Whitsitt Chapel track featuring rapper Yelawolf and co-written with McBryde, “you can’t unlive where you’re from.”

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It’s April 20 — the widely recognized day of celebration for cannabis enthusiasts — and by the smell of it, Jelly Roll has already partaken by the time he arrives at the Grand Ole Opry, where Billboard first meets him. “As I walked in here, my publicist was a little worried about it, and I said, ‘Let me tell you something: I’m as high as I can be every time you’ve ever seen me,’ ” Jelly admits with a shrug. “The day doesn’t change that.”

As it is for so many country artists, the Grand Ole Opry was “holy ground” to Jelly even before he made his debut there in November 2021. After being released from jail in 2009 — while still wearing an ankle bracelet — he scraped together the money to see Craig Morgan there; while incarcerated, Jelly would play his 2002 hit “Almost Home” endlessly. He cried as Morgan played the song at the Opry, thinking, “’That’s what I want to do. I want to make people feel the way this makes me feel.’”

Several times during the day, Jelly steps outside to smoke a joint. He says it’s “better than Xanax” for his mental health and anxiety (he’s launched his own cannabis line, Bad Apple). He has cut down somewhat on his drinking and stopped taking the other harmful drugs “that really had a hold of my life,” including cocaine, pain pills and codeine. But those substances still have a hold on people from his past. “Unfortunately, my friends in Antioch haven’t quit dying from fentanyl or are getting locked up or still doing time. I’m still accepting collect calls to this day.” He estimates he has been to funerals for 30 friends who have died, mainly from drugs.

At April’s CMT Awards, Jelly won all three categories for which he was nominated. But the week was bittersweet. “I’d just had a friend overdose on fentanyl. I missed his funeral because I was camera blocking [for the awards telecast],” he says.

That’s Jelly’s life now. Though he lives on the other side of Nashville from where he grew up, part of him remains firmly planted in Antioch, while another part has Dwayne “The Rock” Johnson on speed dial, sits courtside at a Los Angeles Lakers playoff game in the same row as Adele and proudly shows off his latest chain, with a pendant that reads “Son of a Sinner” in diamonds. After Jelly’s song of the same title became his first No. 1 on Country Airplay, he went to the Icebox in Atlanta — “Where all the rappers like Lil Baby go,” he says — and had identical chains made for him and his co-writers ERNEST and David Ray Stevens.

“New playground, new playmates,” he says of his life today. “I live in a totally different space. But I’m always conscious of keeping in touch with where I’m from. My heart is to help,” he says of his old Antioch connections, even as he admits he has had to cut off old buddies still living what he calls “a certain life. They know I love them, but I can’t afford to risk being on the phone with you and [it] sounds like I’m involved in something I’m not involved with. I might not talk to you, but I’m still bonding you out.” To make a clean break, Jelly recently got rid of his cellphone for several months. Only a handful of people have his new number.

At 23, while incarcerated for drug dealing, Jelly “all but gave up,” he says. “I was like, ‘I’m going to die in prison or young.’ ” Then he experienced what he calls his “road to Damascus” moment. “May 22, 2008. A guard knocks on my cell door midafternoon during lockdown,” Jelly recalls. “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.”

Jelly knew when he went to jail that a woman he had been seeing was pregnant, but he says impending fatherhood had just felt like another mistake in a litany of bad decisions. “I was just irritated by it,” he says. “Like, ‘I’ve really f–ked up now.’ ” But Bailee’s birth inspired him to change. He was granted a transfer from the violent offenders unit to the education unit and started studying for his GED — which, much to his surprise, he passed on his first try. “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 says. “I walked in there and smacked that b-tch out of the park.”

Once released, he met his daughter on her second birthday. “I grilled hamburgers and hot dogs,” he says. Bailee now lives with him and his wife, Bunnie, whom he married in 2016, and he frequently sees Noah (nicknamed Buddy), who is from another relationship. He calls Bunnie, a former sex worker who now hosts the popular Dumb Blonde podcast, “a beacon of change in my life. 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 says. “I would have never got custody of my daughter without her. I wouldn’t have had the stability or the money.”

After his release, Jelly turned to making rap music his career, independently releasing albums, posting music on YouTube and taking any gig he could. From 2010 to 2015, he lived in an old van, driving wherever there was work. “I’d go to Columbus [Ohio] and do $50 features; I’d sell rap verses for 50 bucks,” he says. “I was so petrified of sitting idle because I was afraid I would resort back to what I felt like I knew.”

Though Jelly’s breakthrough on the country charts is recent, he first appeared on Billboard’s R&B/Hip-Hop Albums chart in 2011 with the independently released Strictly Business, a collaborative album with Nashville rapper Haystak. It peaked at No. 67 — which is news to him today: “That makes me want to call my distributor and get an audit on the money,” he says with a laugh.

Over the next five years, Jelly — who taught himself the ins and outs of the music business through various partnerships with artists and both local and national distributors — charted several more albums, including 2013’s No Filter with Lil Wyte, which reached No. 17 on Top Rap Albums. He collaborated with friend Struggle Jennings on the Waylon & Willie series of four rap albums, released between 2017 and 2020, and named after Jennings’ step-grandfather Waylon Jennings and Willie Nelson. The volumes addressed bleak topics including substance abuse and the inescapable weight of a troubled past (even in the pursuit of love, as on the RIAA gold-certified single “Fall in the Fall”).

On such efforts, Jelly would occasionally sing, though he says he was “petrified” to do so for an entire track. But some liquid courage, karaoke and Bob Seger helped him find his voice. He bursts into “Old Time Rock & Roll”: “Risky Business, baby,” he says, name-checking the 1983 movie that gave Seger’s tune a new life. “Any time that song comes on, I’m single for three minutes. I’m Elvis Presley. I’m singing to women. It just brings it out of me.”

“There are not many artists out there that can rap like he does and then switch over to a soulful, melodic voice that’s instantly recognizable,” says fellow country artist and longtime friend Brantley Gilbert, who co-wrote and sings with Jelly on Whitsitt Chapel’s “Behind Bars.” “He is one of the most genuine people you’ll ever meet. He’s consistently himself and never changes who he is to fit a certain mold. He has had some experiences that not many artists in this genre can say they’ve had, so he’s able to open up a whole new world to folks while making those ­experiences relatable to everyone.”

“Save Me” — which initially appeared on Jelly’s 2020 independent album, Self-Medicated, and which he remade with Lainey Wilson for Whitsitt Chapel — was one of the first songs Jelly released as a singer with no rapping. “We were all in the darkest place we’d been in a long time when I wrote that song in May 2020. They were still spraying boxes with Lysol,” he says. “We were all living with our own thoughts a little more than we’re used to.”

His ability to capture the truth of the moment earned Wilson’s respect. “Jelly goes against the grain and is 100% himself 100% of the time,” she says. “I love that about him as a human and an artist.” After “Save Me” came out, labels started calling. “My heart was to do country music and be respected on these streets that I grew up on,” says Jelly, who is now managed by John Meneilly. (Jonathan Craig serves as his day-to-day manager.) “And [BMG Nashville president Jon] Loba got it. But he also knew that I wasn’t willing to give up control of my masters or my creativity, so he was open to us working out a deal that could reflect that. It’s a fair partnership.”

After Stoney Creek vp of promotion Adrian Michaels heard Jelly, he brought him to the attention of Loba, who Googled the video for “Save Me” and was sold. “I saw that pain, vulnerability, that tenderness,” Loba says. “I loved his vocal. I just said, ‘That’s a country song.’ I was convinced his storytelling, his heart and his brand would be accepted by our genre.”

Though Whitsitt Chapel, produced primarily by Grammy nominee Zach Crowell, bears the name and likeness of its namesake rural, red brick church, Jelly made the project for people like himself who may not find salvation on Sunday morning. As he professes on current single “Need a Favor,” “I only pray when I ain’t got a prayer.”

“You’ll never see a man pray harder than as soon as sh-t gets tight,” he says. “I was like, ‘What if worship music is honest? What would my worship song sound like to God?’ ”

History has a funny way of repeating itself. Just as Jelly’s friends took him to church when he was 14, last year, Bailee started attending a small church with her friends and asked Jelly to accompany her — an experience that started him on his path back to Whitsitt Chapel.

“That little back-road church reminded me so much of this little church, and it was just so nostalgic because Bailee’s getting in trouble [and] smoking weed,” he says. “She’s going through what 15-year-olds go through. I went through all that. I know that’s whenever my life turned all the way worse. It started bringing up all these emotions of me being right there on that fence.”

After going to church with Bailee, Jelly ditched all but two of the 70 songs he had written for a new project and started on what would become Whitsitt Chapel, which also addresses the hypocrisy he has witnessed from so-called Christians questioning his faith (particularly on songs like “Nail Me”).

“I never thought that I would do something in life that would make people care to hear my story. So equally, I never thought that my story would ever be judged,” he says. “It just hurt my spirit. It was all happening while I’m cooking this album. I had Christian people that were judging my faith based on my use of language or marijuana or drinking references. I just felt really cornered, and it felt really judgy.”

Loba has a message for any Christians who question Jelly’s faith: “I say to them, ‘He will bring more people to God than 95% of the pastors.’ He is touching an audience that has felt invisible [and] dismissed. On the album, there’s hope that you can be redeemed.”

So for Jelly, Whitsitt Chapel is a starting point, not a destination. “Whitsitt Chapel planted the seed of a higher power. We were a very Southern family, so [we did] a lot of praying before dinner and stuff, but it was the first time I feel like I separated from the house and found God by myself,” he says. “So if I was going to make an album that felt so faith-based, I wanted it to reflect where I felt like it started. I think we’re all trying to wash away something.”

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Jelly Roll loves Winnie the Pooh. He also loves Jim Croce and James Taylor. And he especially loves the 1993 Disney movie Cool Runnings, loosely based on the story of the 1988 Jamaican Olympic bobsled team. “Because 98% of every problem in my life I caused, but one or two times in my life the most heartbreaking things I dealt with was the stuff I didn’t cause,” he explains. “Cool Runnings made me understand that sometimes you can do everything right and the sled still breaks. I needed that for the sh-t I went through in life.”

To sort through the wreckage of his past, he’s in intensive therapy, including “timelining” his life. He’s up to age 12. Therapy “is one of the first things I splurged real resources on,” he says. “I found [trauma] to be like one of the roots of probably my obesity, right? This isn’t a lack of discipline. I run a multimillion-dollar business. I work 12, 15, 18 hours a day. I’m a disciplined man. It’s got to be something else.”

As he fights to “overcome some of these demons that I’ve had to deal with,” he’s also taking Bailee to therapy. “Her father was in jail when she was born. Her mother ended up hooked on heroin and disappeared,” he says. “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.”

He looks at his life in two acts now: Act 1 is the Jelly who used to do bad things; Act 2 is the Jelly of today. “I was a less-than-desirable human in that era,” he says of the time before Bailee was born. “I like to separate myself from that guy like two different people now because it’s the way I’ve made peace with that. And that dude wasn’t a good dude, man.”

Asked if he believes God has forgiven him, Jelly goes silent and tears up. After a long pause, he says, “I think God forgave me way faster than I forgave myself.” As for what it will take for him to forgive himself? “Being a man of service. Trying to care about people.”

In December, Jelly sold out Nashville’s Bridgestone Arena — an astonishing feat not not only because he’s still a developing artist, but because the venue is just a little over a mile from where he turned 15, 16 and 17 as inmate No. 00364950 in Davidson County Juvenile Detention Center. (The run-up to the concert and Jelly’s compelling backstory are captured in the Hulu documentary Jelly Roll: Save Me, which premiered May 30.)

Jelly, who is booked by CAA’s Hunter Williams, donated all his money from the Bridgestone concert (over $400,000) to Impact Youth Outreach and other organizations to, among other things, build studios in that same juvenile detention center, and he has already pledged to help fund a studio in a new building opening at the center in five years.

“More than anything, I just want to try to help these kids” who are now incarcerated, says Jelly. He wants them to understand that he believes in them in the way he wishes someone, anyone, had believed in him when he was younger. He funds programs at the facility to teach kids Pro Tools and offer them classes with visiting producers and engineers. “Who knows where I’d be if they had a real education unit in juvenile at the time,” he says. “If they’d had a studio, if they’d had trade work and I was being inspired every day instead of being reprimanded.”

And his plans go far beyond the detention center. The day before this interview, he bid on a $4 million building in North Nashville that he wants to turn into a community center. Beyond music, helping at-risk kids may be Jelly’s true calling. “Whenever I’m done doing the circus of the music business and I want to leave the carnival and be a normal human, that’s what I’ll do,” he says.

For now, his own honesty and search for redemption are resonating with fans, who comment on his social media that his songs have saved their lives. “Who in life can say they really helped somebody in the darkest moment of their life that was fixing to kill themselves?” he says. “I look at that as something that inspires me to do more.”

He hears the same praise face-to-face. As he leaves Billboard’s photo shoot at an old paint factory, a worker rushes out to tell him that because of Jelly’s music, he’s approaching 18 months of sobriety. Jelly asks the exact date, not once but twice, and tells him he will be thinking of him on that day.

Fans also recognize him and want to party with him — an offer he happily accepts. During a video shoot the day before at Tin Roof, a bar he and his father used to frequent on Lower Broadway, some bros from Pennsylvania shout out his name and filming halts while Jelly joyously glad-hands and buys a round of tequila shots.

Bunnie calls the public smile that hides the pain so evident in Jelly’s songwriting “the Robin Williams effect,” referring to how the late comedian’s outward exuberance masked inner turmoil. “My wife is like, ‘[People] would never think that this lifetime of pain and carrying caskets and death and drug addiction and all this dark sh-t would come out of you if [they] just met you at a bar,’ ” he says.

But those who have listened to his music ­already feel a certain kinship with Jelly — and he has a message for them: “I want to be a guidepost of hope for people to know that losers can win. That who you were isn’t who you are.”

It’s a message he still tells himself. And as he moves forward, he wouldn’t mind if his good works brought him a pardon from Tennessee’s governor. “A pardon would change my whole life,” he says, then quickly adds that he would only accept it if it came with a change of policy for currently incarcerated youth. “Maybe we’re disciplining an age group that should be rehabilitated. I just want to have that conversation, and if it can end in a pardon, f–king let’s go.”

A pardon would mean having many of his rights restored — and should it happen, he may have to take a little joyride around a certain ritzy neighborhood that didn’t believe in second chances. “I’d love to move back to that neighborhood and ride around in my golf cart blaring gangster rap music, flipping people off,” he says with a wry chuckle. “I’m joking, but I’m not.”

This story originally appeared in the June 3, 2023, issue of Billboard.