Just a few years ago, a conversation about Jelly Roll would have likely been related to pastry. 

These days, however, there’s a good chance that discussion would be about the country music phenom.

Who burst on the scene with the force of a hurricane after the release of his 2021 album “Ballads of the Broken.” 

By the time he unveiled his followup, 2023’s “Whitsitt Chapel,” Jelly Roll had utterly conquered Nashville.

A bona fide superstar whose rise to the top was as rapid as it was incendiary. 

Or at least that’s how it may have looked from the outside. For Jelly Roll himself, that overnight success had been well over a decade in the making.

Following years of traveling from town to town, playing to half-empty clubs and sleeping in his van while trying to gain traction for a music career that.

Until that point, had experienced more struggle than success. Pushing 40, those years of floundering have made the superstardom he’s achieved all the more meaningful for him. 

Nowhere was that more clear than at the 2023 CMT Awards, when Jelly Roll emerged as the night’s big winner by taking home three awards. 

“It was an absolute dream come true,” the singer said in an interview with The New York Times, “and I’ve had a worst-case scenario life up to this point.”

This is probably obvious, but Jelly Roll is not the name he was given when he was born in December 1984 in Nashville. Before he was Jelly Roll, the musician was a kid named Jason DeFord. His childhood wasn’t exactly of the white-picket-fence variety; while growing up in Antioch, just outside Nashville, Jelly Roll saw his father earn extra scratch as a bookie, while his mother experienced issues with both mental health and addiction. 

It was his mom, though, who gave him the nickname that he’d eventually use as his stage name. “I was a chunky little kid who loved donuts, and every Sunday after church, I would get one, and my mom would call me Little Jelly Roll,” he said during an interview with StageRightSecrets during 2023’s CMA Fest. The name eventually caught on with his classmates.

As he told “CBS Sunday Morning,” his mother continues to call him by that childhood nickname, all those decades later. Meanwhile, it’s also the name to which he still answers. “If somebody walked in here right now and said, ‘Jason,’ I wouldn’t look up,” he explained.

When he still a kid, Jelly Roll ran afoul of the law. He was just 14 the first time he was arrested and imprisoned, a vicious cycle that he would repeat by spending more than 40 stints in prison during the next 10 years of his life. When he was 16, Jelly Roll was convicted of aggravated robbery, facing a sentence of up to 20 years behind bars. “They were talking about giving me more time than I’d been alive,” he mused in an interview with Billboard.  “I was charged as an adult years before I could buy a beer, lease an apartment, get a pack of cigarettes,” he added. 

At the time, he began to feel that he’d be calling prison home for the rest of his days. “There was a time in my life where I truly thought … this was it,” he admitted during an interview with “CBS Sunday Morning.”

He wound up spending more than a year in prison. Looking back, he retains deep regrets for committing the act that placed him behind bars. “I never want to overlook the fact that it was a heinous crime,” he told Billboard. “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.”

While serving a stint in the slammer related to dealing drugs, Jelly Roll learned some life-changing news. “A guard knocks on my cell door midafternoon during lockdown. He goes, ‘You had a kid today,'” Jelly Roll told Billboard. Instantly, he was struck with a sense of purpose he’d never had before; now, he was suddenly responsible for a tiny human being. “Just the realization that I could no longer be selfish,” he said in an interview with 107.5 The Point. “And that there was something that was solely relying on me. I knew that that was an important task.”

Looking back, Jelly Roll now views that singular moment as the most defining event in his life. “I compare it to the Christian scripture of when Saul turned into Paul on the Damascus Road,” he said in an interview with People about how Jelly Roll’s daughter, Bailee Ann, changed everything for him. “It was kind of that moment for me.”

He decided he would do whatever it took to become a part of his daughter’s life. That meant altering his behavior behind bars, which resulted in a transfer from the prison’s violent offender unit to its educational unit, where he hit the books and earned his GED. After his release, he met his daughter for the first time at a party celebrating her second birthday. In 2016, Jelly Roll’s second child, a son named Noah, was born. 

Jelly Roll’s journey toward country music has been a circuitous one. Despite being born in Nashville, the global epicenter of the genre, he’d been more interested in rap than country. “The culture I was first exposed to was hip-hop,” he told Billboard. “Not even just music, but the culture — breakdancing, graffiti, freestyling, the clothing.” Eventually, he began creating his own raps, and recorded them on CDs that he’d hand out as a free bonus to the people to whom he sold drugs. “I’m just like, ‘Yo, here’s a sack of weed. Here’s a gram of coke. Here’s a mixtape.’ Know what I’m saying? ‘I rap, too!’ It was like my business card,” he told “CBS Sunday Morning.” “Even my drug dealing, to me, was always a means to music.”

He spoke to Billboard just before making his debut at Nashville’s Ryman Auditorium, admitting that he’d never envisioned himself performing on what is arguably the city’s most iconic stage. “I dreamed of being on that stage since I was a kid but never thought I would — because I came from the rap and hip-hop world and now I live in the rock/country space,” he said. “I’ll be the third ‘rap act.’ Wu-Tang, Common and Jelly Roll.”

His shift from rap to country, he told The New York Times, was something of a natural evolution. “The music started evolving as the man did,” he explained.

In 2013, little-known rapper Jelly Roll issued a new mixtape, titled “Whiskey, Weed and Waffle House,” with cover art featuring a bottle of Crown Royal whiskey, a marijuana leaf, and the Waffle House logo. Not long after, he received a letter from the restaurant chain, threatening to sue over unauthorized use of its logo.

“When I first got the cease and desist letter I thought somebody was pulling my chain,” he said in a statement, as reported by HipHopDX. “I thought, ‘Surely I’m not known enough for Waffle House to give a s*** about me using their name.” Wanting to avoid being sued, he quickly changed both the artwork and the title, removing the logo and retitling the disc as “Whiskey Weed and Women.” As he later told Gawker (via Whiskey Riff), he was surprised that Waffle House would take issue at all. “Have you all ever went into a Waffle House after 8 p.m.?” he asked. “It looks like an old pregnant woman strip club that sells hash browns! And then, like, me putting a little pot leaf beside their logo — that’s the worst you’ve ever looked?”

Looking back on the whole thing in a 2021 Instagram post, he viewed the legal threat as a blessing because of all the attention he received, including that Gawker feature, and even a mention by Jimmy Fallon in a “Tonight Show” monologue. “Long story short my fat ass holds no grudges,” he wrote.

Jelly Roll started selling and using drugs when he was still a teenager, and he spent a significant part of his younger years in and out of prison. Learning that he’d become a father while behind bars proved to be the wakeup call he needed to end his drug use once and for all. As he told The Guardian, he kicked hard drugs without resorting to rehab or a 12-step program, although he continued to smoke marijuana and drink alcohol. “I walk the line when I talk about my recovery out of respect for the people that have actually worked the program and completely sobered up,” he said.

Admittedly, the most difficult part of the process for him had been changing the association he’d created between drugs and alcohol. “I had to learn that you could drink alcohol without doing cocaine. It took me a long time to learn that,” he explained. “There was a long time where I just assumed, when people told me they drank without doing cocaine, I was like, I thought we only drank to do cocaine.” In fact, the reason he drank liquor while imbibing cocaine was because it made him feel like he had less of a problem with drugs. “Nobody wants to snort cocaine sober, then you’re a drug addict,” he said. “But I had to re-look at my relationship with alcohol like that.”

Another life-changing moment for Jelly Roll came in 2015, when he met his future wife, Bunnie Xo. At the time, he was a dirt-poor rapper living in his van, while she was a high-end sex worker — not exactly Ozzie and Harriet. Their connection, however, was immediate, and they soon began dating. 

One night, Jelly Roll was performing in a Las Vegas nightclub, with Bunnie in the audience, when he spontaneously decided to propose while onstage. When Bunnie said yes, he figured, why wait? “I’m like, ‘F*** it, let’s just go now.’ She’s like, ‘The courthouse is open for like … 44 more minutes,” he revealed in a TikTok video.

Years later, the couple decided the time was right to have a real, genuine wedding. As Bunnie revealed via Facebook in July 2023, she and Jelly Roll would be renewing their vows — in the same wedding chapel in which they got hitched all those years earlier. This time, however, she was planning on doing things right. “I’m going to wear a real wedding dress since I didn’t the first time we got married in that little chapel in Vegas,” she wrote. Jelly Roll later took to TikTok to share a video from their vow renewal, featuring his bride in her spectacular white gown. “Seven years ago we stumbled into this little chapel in Vegas black out drunk,” he wrote. “My only regret was never seeing her in a dress.” 

Just as Jelly Roll’s wedding to Bunnie Xo wasn’t exactly typical, the same can be said of their marriage. The fact that they may appear to be an unusual match is not something that’s lost on them. “I’m not J’s type, and he’s not my type,” Bunnie explained while appearing on the “Wife of the Party” podcast. There was also, of course, the fact that Bunnie maintained her career in sex work, while Jelly Roll was unfaithful shortly after they tied the knot. “We got married in 2016. The affair was started with an ex in 2017, and then I think I found out about it early on in 2018,” she said on the same podcast episode, revealing she was ready to call it quits but ultimately worked through it. 

Meanwhile, the two have been very candid about having an open marriage. “If I want to sleep with another guy, I can go sleep with another guy,” she explained in an episode of her “Dumb Blonde” podcast. “Like, that’s not a problem.”

They’re also not averse to inviting others to join them in the bedroom. Interviewed by 247HH, Jelly Roll recalled the shenanigans they got up to when she accompanied him on the road for his “Addiction Kills” tour. “Lansing, Michigan she brought like three women on the bus, and that’s great,” he said. “She’s done that more than three or four times, which isn’t a crazy thing at that point.”

Jelly Roll has long connected with his fans by harnessing the power of social media. Over the years, he’s been active on Facebook, Instagram, YouTube, and TikTok, amassing millions of followers along the way. 

However, in early 2024 he decided to quit social media. As his wife, Bunnie Xo, explained, trolls’ cruel comments got to be too much. “My husband got off the internet because he is so tired of being bullied about his f***ing weight,” she revealed in a video she shared on TikTok. “That makes me want to cry because he is the sweetest angel baby.” According to Bunnie, her husband is a lot more sensitive about his size that most people realize. “The internet can say whatever the f*** they want about you and they say, ‘Well you’re a celebrity, you’re supposed to be able to handle it.’ No the f*** you’re not,” she said.

Jelly Roll himself opened up about quitting social media, revealing that there were other reasons behind his decision beyond the bullying and fat-shaming. As far as the musician was concerned, his relationship with social media in general wasn’t in a good spot. “It was not only the toxicity of social media, but the addiction of it. I was becoming too busy to waste hours of my life scrolling,” he told Variety. “I’ve never felt better or healthier mentally — never felt more clearheaded,” he added. 

Jelly Roll has long lived in a world in which drug addiction was omnipresent, in the lives of his friends, family, and even his own. In early 2024, he brought that experience to Capitol Hill when he testified about the need for more powerful legislation to combat the fentanyl epidemic that has taken so many American lives. Speaking before the Senate’s Banking, Housing and Urban Affairs Committee, he brought his personal perspective. “I’ve attended more funerals than I care to share with y’all, this committee. I could sit here and cry for days about the caskets I’ve carried of people I love dearly, deeply, in my soul,” he told the committee, as reported by CNN.

Jelly Roll’s wife, Bunnie Xo, sat behind him as he spoke from the heart, urging U.S. senators to pass the FEND Off Fentanyl Act. He also acknowledged the irony that he, a convicted felon and former drug dealer, was speaking out about that particular issue. “I brought my community down. I hurt people,” he said, taking responsibility for his own small role in the fentanyl crisis. “I was the uneducated man in the kitchen playing chemist with drugs I knew absolutely nothing about, just like these drug dealers are doing right now when they’re mixing every drug on the market with fentanyl,” he said. “And they’re killing the people we love.”

There’s no denying music is Jelly Roll’s passion, yet over the past few years he’s taken up a hobby that he’s become keenly interested in. “My guilty pleasure is golf,” he told Billboard, one of several revelations that he felt fans probably didn’t know about him. “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.”

The golf-loving country superstar was ready to buy his dream home within a gated community abutting a golf course — until his criminal past resurfaced and put the kibosh on that plan. As he revealed during an appearance on “The Joe Rogan Experience,” his offer had been accepted, and the deal was about to be done. “They turn me around and say, ‘No, the golf course won’t let a felon be a part of the community,'” he ruefully recalled. 

There have been many country music stars who’ve also established themselves as actors — for proof, check out the IMDb pages of Willie Nelson, Reba McEntire, and country legend Dolly Parton, just to name a few. If Jelly Roll has his way, he’ll be joining that illustrious group of singers-turned-actors, and he has a very specific project in mind for his eventual acting debut. 

During an interview with ABC News, he took the opportunity to issue a personal plea to Ryan Murphy, executive producer of one of his favorite TV shows, “American Horror Story.” “Ryan, please call me, man. I know you don’t know me. If we could do a 30-minute Zoom and just let me hard sell you on why I should be in the next ‘American Horror Story,’ I’d appreciate it,” he said. “Ryan Murphy. Yell at me. I’m shooting at you every time I get a chance on a national platform. Ryan Murphy, I’ll get my people with your people. I just need 15 to 30 minutes.”

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Source: The Wall Street Journal