Jelly Roll is Entering a New Chapter as a Bona Fide Celebrity; So Who is He as an Artist?

Convicted felons in Tennessee are stripped of so many of their rights, even after they're done serving time.

Jason Bradley DeFord, otherwise known as Jelly Roll, was convicted of armed robbery in 2000; he can no longer vote, own a firearm, receive government benefits, or hold public office. But one thing the state can never take away from him is his right to write songs, make music, play sold-out shows and rise to the level of a bona fide superstar.

Those rights can never be denied.

Nor should they be. After spending around 11 years in and out of prison as a juvenile and an adult, Jelly Roll has done his time. He should be able to move on, live his life and hone his craft with his liberties intact. Which is precisely what he's doing today.

In country music, the most common piece of advice is to write what you know. And man, does he ever. Jelly Roll's country songs are filled with darkly honest themes of redemption, addiction, trauma, regret, loneliness, rehab, suicide, recovery, rock bottom, mental illness, depression, sin and, sometimes, triumph over all of it. If you're scrolling through country songs looking for party anthems about bikinis, barbeques and bonfires, he's not your guy. But after nearly 40 arrests and convictions, he is using his life story for good. That's his lane, and the genre is better off because of it.

If he'd walked out of prison for the last time in 2009 with his knapsack full of handwritten songs and tried his hand at bro-country, summertime tunes, boyfriend-country love songs or rodeo cowboy anthems, it would have been disingenuous. So, he became the kind of country singer country music didn't already have.

It all started in Antioch, Tennessee, about 15 miles south of the honky-tonks on Nashville's Lower Broadway. Antioch was Jelly Roll's home – one with hands-off parents and a litany of bad choices – where he started getting into trouble as a young teenager. By the time he was 14, he'd started a decade of stints in jail for drug possession when what he really wanted to be doing was rapping. When he looks back on those dealing days now, he admits trying a gift-with-purchase program to promote his music: every time he sold someone heroin, cocaine, marijuana and/or Xanax, he'd gift the customer a free mixtape he'd made.

Jelly Roll's past and future are divided by the Metro-Davidson Country Detention Facility, which sits halfway between the Nashville music scene and Jelly Roll's hometown in Antioch. That was where he was sent after being convicted of aggravated robbery with a weapon in 2000 when he was just 16. He has described life on the inside as almost safer and more predictable than life on the streets. But regardless of where he was, on the street or in jail, the common denominator was always his music. He was resourceful, writing hundreds of songs when locked up, using his cell's metal bed frame as the percussion to map the melody in his head.

Being in prison quickly became his new normal, as if he'd conceded that there was no other kind of life for him. But in 2008, he got word that a former girlfriend had given birth to a baby girl, and that she was Jelly Roll's daughter. Suddenly, there was an urgency. To get out, provide, man up and become the father he needed to be. He was released from state prison a year later with a GED and a purpose. His daughter, Bailee, is 16 now, and Jelly Roll and his wife Bunnie XO are raising her and her half-brother, Noah, who was born in 2016.

But this isn't a Cinderella story where Jelly Roll walks out of prison and onto the stage of the Grand Ole Opry. There were a solid 12 years between his release and his Opry debut. He made a living as an up-and-coming rapper by playing shows for $50 a night while sleeping in the van he'd used to get from show to show. It took a while, but it built character, helping him break the cycle he'd been in since he was a teenager.

Back then, his music wasn't even slightly country. He was a rapper with a very, very bright future. Even in archived footage from his shows back then, it's easy to see how he could've ended up as the next Eminem. While still an independent rap artist, he built up a robust YouTube following from virtually nothing. Admittedly, country music changed things for him; while he was playing in small theaters during those post-prison years, he's now playing for audiences closer to 100,000. He declared his Rodeo Houston show earlier this year – with 75,000 fans – as his biggest one yet. Most of that credit goes straight to Jelly Roll for being the voice of the common man telling his truths, even when they are uncomfortably candid.

Nashville's Broken Bow Records also had something to do with it. They were the one record label that allowed him to keep doing what he was doing. Change just wasn't on the agenda. There was no insistence that he put on Wranglers and a cowboy hat. They encouraged him to stay on the road he was on. When he started singing instead of rapping, that changed everything.

Now, his list of awards and nominations is longer than his rap sheet: two Grammy nominations, one ACM Award win, eight iHeart Radio Awards nominations, four People's Choice Awards wins, five CMA nominations, and three CMT Music Awards wins. All from just two major-label country albums in the past two years, Whitsitt Chapel (‘Need a Favor’, ‘Save Me’, ‘Halfway to Hell’) and the brand new Beautifully Broken (‘I Am Not Okay’ and ‘Liar’). He's breaking genre history with his steady stream of singles that consistently top the charts.

No one is more pleased with that than Jelly Roll. His genuine attitude of gratitude have made him and his kind heart almost as famous as his music. He has become well-known for telling anyone who will listen that what's in front of us is so much more important than what's behind us. He's not just all talk, either. His official Beautifully Broken Charities include Folds of Honor, National Alliance on Mental Illness, Shatterproof and Wounded Warriors.

He is also dedicated to using his platform for all kinds of good, to raise awareness and funds for at-risk youth nationwide. This includes visits to the Nashville Detention Center, where he spent many formative years. He has even partnered with Impact Youth Outreach to donate $250,000 to construct a recording studio there. As addiction has plagued so many of the people in his life, Jelly Roll recently delivered testimony urging Congress to pass anti-fentanyl legislation as part of the bipartisan Fentanyl Eradication and Narcotics Deterrence (FEND) Off Fentanyl Act. It was the kind of testimony only a man who lived it and survived it could give. Just three months after his plea, the bill was signed into law.

Today, Jelly Roll is sort of sober. He's admitted he still has a cocktail now and then and still smokes weed. He is also happily married, after meeting his wife, Bunnie XO, when he was playing a Las Vegas concert in 2015. They married soon after, and her Dumb Blonde podcast – where she describes herself as Trailer Park Barbara Walters – was launched a few years later. Her past as a sex worker, high-end escort and OnlyFans creator is just that: past. She quit the business and shut everything down for good in 2023, focusing solely on her podcast and her husband.

Together, they have nearly five million followers on Instagram alone, where you'll find they both have an affinity for tattoos. Hers on her body, his on his body and his face, from the small crosses in the corner of each eye to the large cross on his cheek to the Music Man label on his forehead. Whether or not ink is your cup of tea, it's impossible to ignore Jelly Roll and Bunnie XO's positive impact on their friends, followers, fans and the music industry at large. One of the songs on his new album, ‘Hey Mama’, is the first time he's allowed the world to see inside their love within a song.

Beautifully Broken, which sold 161k equivalent album units in it's first week of release and gave the larger-than-life artist his first No.1 Album on the Billboard Chart on Monday (October 21), is more evidence that Jelly Roll is here to stay. While the genre is no stranger to artists with DUI arrests and felonies dating back to Merle Haggard's grand theft auto, Jelly Roll is one of few to have accomplished the enviable feat of leaving that life of crime behind and starting afresh, using his dark past as fodder for future music. Beautifully Broken starts up seamlessly from where Whitsitt Chapel left off.

He invented this lane, after all, so it's not likely he will stray from it. As long as it is human nature to endure suffering, he will be there with songs about it. The new album hits on many of those themes, much like the first one. On 'Unpretty', he admits that he hates the man he used to be, but he'll always be a part of him. On 'Get By', he opens up about his current state of semi-sobriety. On 'Winning Streak', he paints a candidly dismal picture of a typical AA meeting.

This time around, there's more of a holy feeling to some of the arrangements. Choirs, gospel hand claps, pipe organs and lyrics about prayer find their way into many new songs. The final track, 'Time of Day', is a collaboration with rapper MGK. It could've easily been Chris Tomlin on the other mic.

For the country fans who live life with rose-colored glasses on, Jelly Roll's personality and his music will likely go hand-in-hand. Possibly forever. That motivational-speaker persona he shares with the world seems to be who he really is. So when you see him picking up more inevitable music awards down the road, you'll continue to hear acceptance speeches about so much more than the awards. He uses those CMA and ACM stages like his pulpit, continuing to share his relatable stories about triumph. He isn't saying, "How do you like me now" as much as he's preaching "If I made it up here, anyone can."

Suppose he can stay true to the kinds of songs that brought him here and not let the celebrity get in the way of it. In that case, the result will be music so venerated that country fans are sentenced to life with Jelly Roll.

Jelly Roll's new album, Beautifully Broken, is out on October 11th, 2024 via Broken Bow Records and Republic Records.

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