The Untold Truth Of Country Singer Jelly Roll

It's not hyperbole to describe Jelly Roll's rise to the top of the music business as nothing short of meteoric. At the start of 2022, he was an on-the-rise rapper who'd built up a small but devoted following. By the end of that year, however, he had arrived, selling out Nashville's 20,000-seat Bridgestone Arena. Since then, he's experienced a streak of uncanny success with his 2021 major-label debut, "Ballads of the Broken," and his 2023 follow-up, "Whitsitt Chapel." On the strength of those albums' singles, he's broken chart records to emerge as a bona fide Nashville superstar. Heck, he's even been invited to perform at the Grand Ole Opry, the undisputed sign that an artist has been accepted into the country music community. In 2023, his single "Son of a Sinner" — which crystallized his evolution from rap to country — brought him three CMT Awards at that year's ceremony. "They let a loser win tonight!" he declared in one of his three acceptance speeches, referencing his rags-to-riches ride. 

Of course, it isn't just Jelly Roll's music that's memorable. The man himself cuts quite a distinctive figure, so to find out more about this fascinating artist, read on to explore the untold truth of country singer Jelly Roll.

He got his nickname from his mom

Clearly, Jelly Roll is not the name he was born with — that would be Jason DeFord. His stage name, he explained during an appearance on "The Bobby Bones Show," came from his mother. "So, I obviously look the part," he said. "My mother named me that whenever I was a little chubby kid. Been fat my whole life ... I spent the next 30 years trying to grow into the name, I think I've done it."

As he explained in an interview documented by MyRadioLink, his childhood love of donuts also contributed to the nickname. However, in an odd twist of fate, a friend from school — who had a nickname of his own, One-Arm Clay — began calling him Jelly Roll in public, and the name fit so well that he kept it. "I love this because there's a different between a nickname and a stage name," Jelly Roll explained. "You know what the difference is? You don't get to pick your nickname."

While Jelly Roll's stage name has certainly been attention-getting, he's also admitted that there had been a down side, particularly when he was starting out and trying to gain some traction with his music career. "My name is something that has always held me back in my career to a degree," he wrote in a 2014 Facebook post. "To people who have no clue who I am the name seems like a joke or some sort of a gimmick."

Growing up in Nashville influenced his musical journey

Once he'd settled on using the moniker professionally, Jelly Roll felt he had no choice but to stick with it. "One of the reasons I never changed my name is because I felt like it represented Nashville and the culture of the real Nashville ... I was born and raised in this place," he wrote on Facebook.

As he told Music Bliss, he grew up in the Nashville neighborhood of Antioch. "One of the best things about Antioch for me is the fact, and I have said this multiple times in the past, but Antioch is the cultural melting pot of Tennessee," he said, highlighting the various ethnic groups that populated the neighborhood. As a result, Jelly Roll explained that growing up in that kind of environment effectively took race out of the conversation. "Everyone from there... all of us were just so different and so f***ing weird that race didn't make a difference where I'm from," he explained.

Despite growing up in the home of country music — a place literally nicknamed Music City — Jelly Roll sidestepped the influence of country — at least early on — as he gravitated toward Nashville's burgeoning rap scene. "The culture I was first exposed to was hip-hop. Not even just music, but the culture — breakdancing, graffiti, freestyling, the clothing," he told Billboard. "I didn't know there was this other country music culture in town. You just knew the culture you were exposed to."

He's served time in prison

When Jelly Roll was just 14, during a period when his home life was in turmoil (due to his parents' divorce), he got into a fight that landed him in a juvenile detention center. That, he told Music Bliss, sparked a pattern of incarceration that saw him go in and out of jail for more than a decade. "Half of my life, half of my life to date I have been under the eye of the system," he mused. "It's just crazy, man."

At 16 he was charged with aggravated robbery, and tried as an adult. "I never want to overlook the fact that it was a heinous crime," he told Billboard. Facing a potential 20-year sentence, he wound up spending just over a year behind bars. "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," he added.

At age 21 he was charged with possession of drugs, with intent to distribute, resulting in more time behind bars. He vowed to never return. "The truth about me being locked up again, is that I would rather be killed than spend any more time in prison," he told Music Bliss. 

The birth of his daughter completely changed his life's path

During one of his stints in prison, Jelly Roll's daughter, Bailee Ann, was born. As he told Music Bliss, he missed her birth, her first words and steps, and many other important milestones. By the time he was released and he met her for the first time, she was a walking, talking toddler. "So when I came home I realized that I had missed a lot and I wanted to try and catch up," he explained. "Her birth taught me that there is nothing important in eternity than the relationships that we have," he added.

Jelly Roll became even closer to his daughter when he was granted custody of her while her mother battled drug addiction. This proved to be a game-changing experience for both father and daughter. "In 2016, my life changed forever, for the better," Bailee Ann wrote in an Instagram post, recalling when she was placed into her dad's custody.

Interestingly, as she grew to become a teenager, Bailee Ann hadn't taken all that much notice of her dad's burgeoning music career until it really exploded.  "The cool thing is she didn't realize it was happening until now," Jelly Roll told Taste of Country. "Weirdly enough, no matter how successful I've been on the independent level, it's like playing the [Nashville's] Bridgestone [Arena] and stuff like that has made her go, 'Okay, dad's on fire! This is a big deal.'"

If you or anyone you know needs help with addiction issues, help is available. Visit the Substance Abuse and Mental Health Services Administration website or contact SAMHSA's National Helpline at 1-800-662-HELP (4357).

He was a big fan of Waffle House until they threatened to sue him

Waffle House is a Southern institution boasting some 1,500 restaurants. Jelly Roll made his love of the chain known with his 2013 mixtape, "Whiskey, Weed and Waffle House," which he handed out for free at various Waffle House locations. Within weeks of the release, Jelly Roll received a cease-and-desist letter from the chain's law firm, asserting that his use of the restaurant's logo on the album's cover constituted copyright infringement. 

The rapper, who wasn't nearly as well known as he'd eventually become, was stunned that he attracted the chain's attention. "When I first got the cease and desist letter I thought somebody was pulling my chain," he said in a statement, per HipHopDX. "I thought, 'Surely I'm not known enough for Waffle House to give a s*** about me using their name." He responded by rereleasing the mixtape with a new Waffle House-free title — "Whiskey, Weed and Women" — and removing the logo. 

Speaking with Gawker, he admitted he was stunned that Waffle House — not exactly what one would describe as a haute-cuisine, fine-dining establishment — would balk at being associated with someone he felt represented its typical customer base. "Have you all ever went into a Waffle House after 8 p.m.? It looks like an old pregnant woman strip club that sells hash browns!" he quipped. "And then, like, me putting a little pot leaf beside their logo — that's the worst you've ever looked?"

He's been influenced by some iconic outlaw country artists

Jelly Roll began his career with both feet planted in the rap genre. In 2022, however, he decided to lean more into his Nashville roots by infusing country music into the mix. That was certainly true with his 2022 single, "Son of a Sinner," featuring a twangy country sound and lyrics to match. "I think they love it," Jelly Roll told Taste of Country of his fans' reaction to his crossing over into country. "I think a lot of them have grown with me, so a lot of my transition has just been a coming of age."

His new musical direction incorporated some famous singers who rose to fame during the outlaw country movement of the 1970s, and more. In fact, his musical influences are far more eclectic than most people might realize, ranging from Three 6 Mafia to Bob Seger to James Taylor. "Some of my favorites ... Jim Croce ... love the old outlaw stuff. I love ... old Willie [Nelson]. I love the old Waylon [Jennings] records. Huge fan of all the old [Johnny] Cash stuff. These are probably the guys who really molded my style and sound."

In a 2023 interview with the The New York Times, he opened up about why his music had changed the way it did. "The music started evolving as the man did," he explained. "The older I've gotten, the more I've found my singing voice and my love for instrumentation."

He got engaged and married on the same day

As fans of Jelly Roll know, he's not single, and is regularly accompanied by his wife, Bunnie XO. They married in 2016, after dating for about a year. One night while in Las Vegas, the Nashville rapper popped the question to the former sex worker — while he was onstage at a Deftones concert. After the concert, he decided they should get hitched right then and there. "I'm like, 'F*** it, let's just go now.' She's like, 'The courthouse is open for like ... 44 more minutes," he said in a TikTok video, revealing they each said "I do" just before midnight.

At the time that he and Bunnie tied the knot, Jelly Roll's life was a far cry from what it would become. "I was a lost cause, I was in the middle of custody battle, I was broke, living out of van doing 200 shows a year for $200 a show," he wrote in an Facebook tribute to his spouse. As he explained, she quite literally turned his life around. "It was truly the turning point in my career and life," he added, crediting Bunnie with helping him get custody of daughter Bailee Ann. 

Bunnie, however, wasn't content to merely be the wife of a successful country-rap star, and forged her own identity with the launch of her "Dumb Blonde Podcast." Among the various guests she's interviewed have been Jelly Roll himself, who appeared in a June 2020 episode.

He performed a touching duet with his daughter

That old saying about the apple not falling far from the tree certainly applies to Jelly Roll and his daughter, Bailee Ann. He invited her to join him for a duet on his single, "Tears Could Talk," after she'd previously appeared (as a little girl he pushed on a swing) in his music video for "Sunshine After the Rain." 

During a 2022 concert in Houston, Jelly Roll surprised the crowd when he invited Bailee Ann to join him for a live performance of their duet. In a fan-shot video, Bailee Ann proved to be a natural performer as she joined her dad onstage in front of thousands of cheering fans to perform her rapid-fire rap from the single.

The following year, he brought Bailee Ann onstage to perform the song at a concert in Alpharetta, Georgia. As the video documented, he told the crowd about how "Tears Could Talk" came to be. As he recalled, she'd approached him, at around age nine or 10, to share that she'd like to start writing songs as a form of therapy. "And I said, 'Well, I'd love for you to write something and if it's good, we'll put it on my album,'" Jelly Roll told the audience. "And a few years back we did."

He's become an advocate for incarcerated young people

Having been in and out of jail between the ages of 14 and 28, Jelly Roll knows all too well how difficult it can be to escape the pattern of incarceration once a person enters the system. Having been able to turn his own life around, he decided to use the platform he'd developed as a celebrity to help others in circumstances similar to those that he was in. 

In 2022, Jelly Roll demonstrated the depth of his commitment when he donated $250,000 to fund programs serving Nashville youth who'd been incarcerated. Partnering with Nashville-based Impact Youth Outreach, one of the projects to be funded was Jelly Studio, a recording studio that could be used by the young people serving time at Davidson County Juvenile Detention Center — the same institution where Jelly Roll himself had his first experience behind bars. His donation also funded five $10,000 scholarships, along with some other initiatives. 

"Music is my passion, so it's the first thing that I know how to bring to people," he told The Tennessean of why he decided to fund a recording studio within a juvenile detention center. Of course, as he told the The New York Times, partnering with Impact Youth Outreach was only the beginning of what he envisioned himself accomplishing. "That's not even scratching the surface of my plan," he said. "I'm going to build halfway houses and transitional centers — that's my real heart."

His guilty pleasure isn't what fans might expect

When he's not writing, recording, or performing music, Jelly Roll has embraced a hobby that might seem odd for someone with a prison record and multiple face tattoos. "My guilty pleasure is golf," he told Billboard. "I love golf because people drink early in the morning. I, too, like things that involve drinking early in the morning when that's possible. It's like a little sanctuary, man. It's awesome."

When the opportunity arises, Jelly Roll is happy to blend his passion for golf with his philanthropy, which was the case when he shared a photo in an Instagram post, in which he was participating in a charity golf tournament to fund CreatiVets, a nonprofit serving wounded military veterans. He also competed in a 2023 celebrity golf tournament, playing alongside the likes of "Dukes of Hazzard" alum John Schneider, "Sabrina the Teenage Witch" star Melissa Joan Hart, and singer RaeLynn.

However, his past prison record came back to impact his love of golf when he attempted to buy a home in a Tennessee community that boasted its own golf course. Because of his criminal past, he was denied. "Imagine changing your life in such a way that you can afford the kind of house in this community I was looking at," he mused in an interview with Billboard. "My money was welcome, but I wasn't, all because of something I did [almost] 24 years ago."

He's been open about his issues with addiction

While Jelly Roll has been candid about his past troubles with the law, he's also been characteristically open about how substance abuse was a big part of those troubles. "In the beginning, I did a lot of drugs. I drank a lot of codeine, a lot of cough syrup," he told Billboard. "I took a lot of Xanax, did a lot of cocaine, just really took it overboard. I've had years — dude, I don't remember years."

As he explained, his family has a long history of addiction, including his mother, who'd managed to overcome her own issues. "I've had so much addiction around me and so many people around me lose their life or lose their families, or lose somebody they love over an addiction," he told Taste of Country. 

However, he was also quick to point out that while he no longer indulges in the kind of substances he once did, his current lifestyle doesn't exactly encompass the dictionary definition of sobriety. "I definitely enjoy a drink and a cocktail," he added, "but right now I haven't drank in two weeks because it's been all focus for what I got going on in my life.

If you or anyone you know needs help with addiction issues, help is available. Visit the Substance Abuse and Mental Health Services Administration website or contact SAMHSA's National Helpline at 1-800-662-HELP (4357).

He sees his music as therapy for himself and his listeners

Ever since he began focusing on music after being released from prison, Jelly Roll has approached the concept of songwriting and performing with a Herculean level of zeal and intensity. He also made a conscious decision to be completely honest in his music, stripping away all facades until only the truth remained. "Complete vulnerability is my constant goal in writing. Music was the way I found out I wasn't alone," he told Billboard.

That's why his music tends to take an unflinching look at the experiences he's had in his life, something that's particularly true of his songs "Dancing With the Devil" and "Hungover in a Church Pew." As he told the The New York Times, those two tracks — the final songs he recorded for his 2023 album "Whitsitt Chapel" — were both written on the same night, and came from a very deep and personal place. "Those two songs were talking to each other, dealing with the same story," he said. 

For Jelly Roll, writing and recording those songs was a cathartic, therapeutic experience, which took the courage to delve back into some dark times from his past. "I was thinking about the choices I made, some horrible decisions," he explained. "My music is a constant cry for help and growth — it tells a story of change, and I wasn't ready for this before now."

He's the subject of a documentary

There's no denying that Jelly Roll's trajectory from prison inmate to Nashville star is a dramatic story. That was evident to documentary filmmaker Bari Pearlman, who told the story of the rapper-turned-country rocker in the 2023 documentary "Jelly Roll: Save Me."

Even for those who thought they knew Jelly Roll and his backstory, the film contained some revelations, including his recounting of going to prison a staggering 40 times. The film's title is taken from his song, "Save Me," and the documentary explained the significance of that song — not just in terms of serving as his own musical cry for help, but also for jump-starting his rise to the top. How important was that song to his career? At one point in the film, he looked back on being thrilled to have sold 1,000 tickets for a show in January 2022, and selling out Nashville's Bridgestone Arena the following December. 

Understandably, watching his life play out onscreen proved to be an emotional experience for the film's subject. "I mean, we got gritty, we got in the trenches together. We let [the producers] get access to the stuff that artists are afraid to let people get access to," Jelly Roll told ABC Audio. "And we told the truth. I'm nervous, but I am excited." In fact, after watching a minute-long teaser, Jelly Roll was overcome with emotion. "I mean, I cried. I cried for like 20 minutes after I watched it," he said.

He's hit No. 1 on both the rock and country charts

Not only is Jelly Roll's personal story a captivating one, so too has been the trajectory of his career. Starting off firmly rooted in rap, he found even greater success when he incorporated elements of country music and Southern rock to create a style that's distinctively his own. 

That journey has been evident in the chart performance of his biggest hits. In 2022, Jelly Roll landed at No. 1 on Mediabase's active rock radio chart with his single "Dead Man Walking." The following year, he once again hit the No. 1 spot — but not on the rock chart. This time out, his song "Son of a Sinner" debuted at the top of both the Mediabase and Billboard country charts. Also in 2023, he broke a longstanding record when he spent 25 weeks on Billboard's emerging artists chart, the longest consecutive number of weeks that any artist had spent on that particular chart. And, as icing on the cake, his song "Need a Favor" also made history in 2023, when the song became the first ever to wind up in the top 10 of both Billboard's mainstream rock airplay and country airplay charts.

He ruminated on his record-breaking status in an Instagram post that detailed the various chart successes he'd experienced from his album, "Whitsitt Chapel." "I woke up and couldn't believe it! Thank y'all again ... wow," he wrote in the caption.