Jelly Roll's career is all about overcoming adversity, so it makes perfect sense that his life turned around for the better when a prison guard delivered some very important news.
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00:00Jelly Roll's career is all about overcoming adversity, so it makes perfect sense that
00:04his life turned around for the better when a prison guard delivered some very important
00:09news.
00:10Jelly Roll was born Jason Bradley DeFord in the Antioch area of Nashville, Tennessee.
00:15His mother bestowed his famous nickname on him when he was young, and it stuck.
00:19His father, Horace, worked for a wholesale meat business, while also pulling together
00:23extra cash by moonlighting as a bookie.
00:26As far back as Jelly Roll can remember, his mother battled addiction while also struggling
00:30with her mental health.
00:32As he recalled to CBS Sunday Morning in 2024,
00:34"'I knew my father booked bets.
00:36I knew my mother struggled with drugs.
00:38So to me, this was just what you did.'"
00:41By the time Jelly Roll was a teenager, he started gravitating towards petty crime.
00:45He's the first to admit that he caused his parents no end of grief during those years,
00:49as he wrote on Facebook in 2019,
00:51"'Many times the police knocked on my mother's door looking for me.
00:55Many nights, she went to sleep worried the phone would ring in the middle of the night
00:58and something would have happened bad.
01:00Many nights she prayed and worried if I would ever get my life together.'"
01:04"'This is Innertown, USA.
01:07It's just middle-lower class America, man.'"
01:09Jelly Roll was arrested for the first time at the age of 14, and over the next decade
01:14or so, he became intimately familiar with incarceration.
01:17The charges varied, ranging from possession of drugs with the intent to sell to shoplifting
01:22and robbery.
01:23His brushes with the law took a darkly serious turn when he was charged with aggravated assault
01:27at the age of 16.
01:29He was charged as an adult and faced a potential sentence of 20 years.
01:32As he recalled to Billboard in 2023,
01:34"'They were talking about giving me more time than I'd been alive.'"
01:38Jelly Roll was ultimately sentenced to eight years, but wound up serving just over a year.
01:42He then spent the next seven years on probation, and wound up returning to prison several times
01:47in the years that followed.
01:48As he later reflected,
01:50I feel like the justice system at that point kind of parked me on my only set path.
01:54"'Anything that hurt people, I wish I could change that.
01:58But I was just a kid, man.'"
02:00During one prison stint in 2008, a guard knocked on Jelly Roll's cell door to deliver some
02:05big news.
02:06As the singer recalled to CBS Sunday Morning,
02:08"'He said, DeFord, you had a kid today.
02:11I said, what?
02:12He said, yeah, yeah, you had a child.
02:14And I was like, what's her name?
02:15And he said, hell, I don't know.'"
02:17That turned out to be the moment that everything changed for Jelly Roll, as becoming a father
02:22made him realize that he needed to get his life back on track — and fast.
02:26As he told People magazine in 2023,
02:28"'I compare it to the Christian scripture of when Saul turned into Paul on the Damascus
02:32Road.'"
02:33"'My daughter saved my life.
02:35She wasn't old enough to even know it.'"
02:37Jelly Roll started studying for the GED, and he passed on his first attempt.
02:41He also ultimately gave himself two options for how to move his life forward — study
02:46to become a social worker, or focus on the music he'd been making since his teenage years.
02:51He chose the latter.
02:53After getting out of prison, Jelly Roll was finally able to see his daughter, Bailey Ann,
02:57for the first time, at her second birthday.
02:59While committing to be a part of her life, he realized that there was something else
03:03he needed to confront — drugs.
03:05He's continued to use marijuana and drink alcohol, but he's managed to leave the harder
03:09stuff behind.
03:10As he told The Guardian in 2023,
03:11"'I didn't have a choice.
03:13It was me or them, and I had to learn to love myself.'"
03:16Jelly Roll is aware that his version of quasi-sobriety isn't for everyone, but he insists that it
03:21works for him.
03:22As he explained,
03:23"'I walk the line when I talk about my recovery out of respect for the people that have actually
03:27worked the program and completely sobered up.'"
03:30"'I represent overcoming.
03:32I represent the guy that wasn't supposed to make it making it.'"
03:35Jelly Roll has been a fan of rap music since his earliest days.
03:38As he revealed to Billboard in 2021,
03:40"'The culture I was first exposed to was hip-hop.
03:43Not even just music, but the culture, breakdancing, graffiti, freestyling, the clothing.'"
03:48As he immersed himself in Nashville's burgeoning rap scene, he also began creating his own
03:53music.
03:54As he grew more confident in his skills, he headed to a recording studio, and then he
03:57handed out his CDs to his customers while dealing drugs.
04:01As he recalled to CBS Sunday Morning,
04:03"'I'm just like, yo, here's a sack of weed, here's a gram of Coke, here's a mixtape.
04:07Know what I'm saying?
04:08I rap too.
04:09It was like my business card.'"
04:11Jelly Roll experienced his first brush with success in 2010 when Pop Another Pill, his
04:16collaboration with Memphis rapper Lil White, became a modest hit.
04:19For the next decade, he slogged away in small clubs while slowly building up a following.
04:24As his popularity grew and he made a gradual shift from rap to country, he was met with
04:28resistance from the powers that be among the country music establishment.
04:32As he told The Guardian,
04:33"'I was told nobody's gonna buy a 400-pound man singing sad songs.
04:37Like, it's just not in the bingo card, for what the climate of music is."
04:41"'Whatever you're dreaming of right now could be too small.'"
04:44In 2013, Jelly Roll released the mixtape Whiskey, Weed, and Waffle House.
04:48The cover art featured a marijuana leaf, a bottle of Crown Royal Whiskey, and the Waffle
04:52House logo.
04:53The new release quickly attracted attention, but not exactly the kind he was hoping for,
04:57as Waffle House threatened to sue him for using the logo without permission.
05:01He initially thought that someone was just joking around with him, but then he altered
05:05the cover and changed the title to Whiskey, Weed, and Women.
05:08Jelly Roll eventually realized, though, that Waffle House's legal threat provided him plenty
05:12of free publicity.
05:13The story was covered by the likes of Gawker, and Jimmy Fallon even joked about it on The
05:17Tonight Show.
05:18As Jelly Roll wrote on Instagram in 2021,
05:20"'Long story short, my fat ass holds no grudges.
05:24I still come by one anytime I'm drunk or hungover.'"
05:28Jelly Roll was performing in Las Vegas in 2015 when he met his future wife, Bunny XO.
05:33Their road to romance was a rocky one, though.
05:35At that time, he was sleeping in his van because he couldn't afford hotel rooms, while she
05:39was working as an escort and was dating someone else.
05:42One night in 2016, she was watching him perform at a Las Vegas club when he surprised her
05:47with a marriage proposal.
05:48She said yes, and since they were already in an area surrounded by wedding chapels,
05:53they figured there was no point in having a long engagement.
05:56They've remained together since then, and in 2023, they renewed their vows at the same
06:00chapel where they got hitched.
06:01This time, Bunny was decked out in a stunning white gown.
06:05Jelly Roll commemorated the occasion on TikTok, while writing,
06:08"'Seven years ago we stumbled into this little chapel in Vegas, blackout drunk.
06:12My only regret was never seeing her in a dress.'"
06:15In 2016, Jelly Roll was awarded custody of his daughter, Bailey Ann.
06:19It was the culmination of a long process.
06:21As he recalled during an appearance on the Bussin' with the Boys podcast in 2023,
06:25"'I have to sit Bunny down and go, look, I have a kid that you know about that I'm fixing
06:30to have to get full custody of.
06:32There's also a woman out there that's pregnant with a kid of mine.'"
06:34"'And Bunny's just like, whew, man, that's a lot.
06:37She's like, but I got you.'"
06:38One big hurdle for Jelly Roll obtaining custody was the fact that he was a broke ex-con.
06:43He credits his wife for helping him to overcome those particular obstacles.
06:47She got them a home that included a room for Bailey Ann, and paid for a lawyer, even though
06:51she wasn't sure where their relationship was headed.
06:54"'She said, no matter what happens with us, I'm gonna help you get this little girl.'"
07:00In 2022, Bailey Ann looked back on this chapter in her life by writing on Instagram,
07:04"'In 2016 my life changed forever for the better.
07:07My dad got custody of me, and so did his wife.
07:10She is the most caring woman I have ever met.'"
07:13The latter half of the 2010s proved to be a make-or-break period for Jelly Roll, as
07:17he continued to build his fan base while evolving from hip-hop to country.
07:21He paid off in a big way in 2020, when the acoustic ballad Save Me revealed the new sound
07:26that he'd been crafting.
07:27When the music video began racking up millions of views, it didn't take long for the industry
07:31to take notice.
07:32As BMG Nashville president John Loba told Billboard,
07:36"'I saw that pain, vulnerability, that tenderness.
07:39I loved his vocal.
07:41I just said, that's a country song.
07:43I was convinced his storytelling, his heart, and his brand would be accepted by our genre.'"
07:48Bill Loba signed Jelly Roll to his label, and in September 2021, he released his first
07:53major label album, Ballads of the Broken.
07:56One of the singles off that album, Dead Man Walking, ended up becoming Jelly Roll's first-ever
08:00number one on country radio.
08:02And then Son of a Sinner topped the charts ten months after it was released.
08:06In February 2023, Jelly Roll set a record by spending 25 weeks in the top spot of Billboard's
08:11Emerging Artists chart.
08:13A few weeks earlier, he had sold out Nashville's Bridgestone Arena, leaving no doubt that he
08:18was now a force to be reckoned with.
08:20Perhaps the biggest theme of Jelly Roll's music is the stranglehold that addiction can
08:25take on someone's life.
08:26So it was hardly a surprise in January 2024, when he traveled to Washington, D.C., to lobby
08:31for anti-fentanyl legislation before the Senate's Banking, Housing, and Urban Affairs Committee.
08:36He encouraged the senators in attendance to pass the Fend-Off Fentanyl Act.
08:40The bill targeted money laundering as a way to shut down fentanyl traffickers in Mexico
08:45and China, which in turn would hopefully lessen the epidemic of overdose deaths.
08:49At one point during his testimony, Jelly Roll admitted,
08:51"...I've attended more funerals than I care to share with y'all, this committee.
08:55I could sit here and cry for days about the caskets I've carried of people I love dearly,
09:00deeply in my soul."
09:01Jelly Roll also addressed his own criminal past, and the role that he played in getting
09:05drugs, including fentanyl, into people's hands during his days as a dealer.
09:09As he explained,
09:10"...I was the uneducated man in the kitchen playing chemist with drugs I knew absolutely
09:14nothing about, just like these drug dealers are doing right now when they're mixing every
09:19drug on the market with fentanyl, and they're killing the people we love."
09:22"...I encourage y'all to not only pass this bill, but I encourage you to bring it up where
09:26it matters, at the kitchen table."
09:28In April 2024, the bill was signed into law.
09:32In early 2024, Jelly Roll's fans began noticing that there was a little less of him to love.
09:36That was certainly evident on May 7th, when he competed in the Two Bears 5K, a race hosted
09:42by comedians Burt Kreischer and Tom Segura, as part of the Netflix It's a Joke comedy
09:47festival.
09:48Jelly Roll trained for the event by embarking on a strict diet and exercise regimen.
09:52As he revealed to People magazine,
09:53"...I'm probably down 70-something pounds.
09:56I've been really kicking ass, man.
09:58I'm doing two to three miles a day, four to six days a week.
10:02I'm doing 20 to 30 minutes in the sauna, six minutes in a cold plunge every day.
10:06I'm eating healthy right now."
10:07Jelly Roll weighed more than 500 pounds at one point, but he conceded that he still had
10:13a long road ahead of him.
10:14As he admitted,
10:15"...I was thinking, I plan on losing another 100, 100-and-something pounds.
10:19If I feel this good down this weight, man, I can only imagine what I'm going to feel
10:22like by the time I go on tour."
10:25If you or anyone you know needs help with addiction issues, help is available.
10:30Visit the Substance Abuse and Mental Health Services Administration website or contact
10:34SAMHSA's National Helpline at 1-800-662-HELP.