American Songwriter March/April Exclusive Cover Story: Jelly Roll Finds Freedom in the Songs 

Jelly Roll has always known how to write for his audience. First his mother, then his community, his fellow inmates, and now an entire part of the population that struggles with drug addiction—or knows someone who does. He speaks to these vast audiences through music, making it clear that it’s more than just a passion. 

“Songwriting is one of the cores of my belief, my value system in life,” he professes to American Songwriter over the phone as he’s driving to the airport to fly to Mexico to play Luke Bryan’s 2024 Crash My Playa for the first time. “Even in my most hopeless situations, I found hope in songwriting.”

The singer, born Jason DeFord, identified as a songwriter around the age of 12 when he would turn his poetry into raps. He feels “blessed” that he understood song structure early on in life. His mom, Donna DeFord, was his first audience. She struggled with mental health issues and drug addiction throughout his childhood, but music was her guiding light out of the darkness. 

Her son embodied that light when he started writing music to connect with her, his poems-turned-raps emulating the “heavy songs” she was listening to at the time like Bette Midler’s “The Rose” and Kenny Rogers’ “The Gambler.” 

“I think I was trying to find a way to connect with my family,” he reflects. “The way my mother operated in that era, I didn’t see her much. But when I did, it was always driven around music. I wrote poems that were very reflective of the music she was playing. I got an instant audience with her,” he continues, adding that his family was “very encouraging” of his music dreams. “It inspired me.” 

The music he was making connected with his audiences both inside and outside of his house. Born and raised in Antioch, Tennessee, just outside of Nashville, Jelly Roll launched his career in hip-hop, which he describes as the “sound of the neighborhood.” He grew up on ’90s rap and hip-hop and was quickly drawn to the rhythmic patterns, “nuances” and “punchlines” of the genre. 

“It was what I understood the most at that age,” he describes, citing local rappers like The Blow Pop Crew, Haystak, Pistol, Rude Awakening, and Kool Daddy Fresh among his favorites. “It was a lot of really cool stuff, especially in that era of hip-hop.” 

Along the way, he became best friends with Struggle Jennings and immersed himself in the local hip-hop scene in the late ’90s and early 2000s. He cut his teeth performing at local clubs where they’d play hip-hop beats and have dance circles known as “hip-hop cyphers.”And of course, he’d show up at almost every freestyle battle he could, at clubs all over Music City. “There was a real culture of hip-hop in the city in that era,” he recalls. 

Another important figure in the Nashville hip-hop scene at that time was future hit country songwriter/producer Zach Crowell, who got to witness Jelly Roll in his element at said freestyle battles. “He was known as the guy who would just freestyle and say any word that would come to his mind,” Crowell recalls of his first memory of Jelly Roll. “When you see someone going for minutes and minutes, they’re in a flow state of creativity.” 

Jelly Roll and Crowell’s paths have long been running parallel. They were both raised in Nashville and got their start in hip-hop before becoming massively successful in country music. After high school, Crowell purchased a drum machine and started making hip-hop beats he’d sell to local rappers, including Jelly Roll, who would also rent studio time from him. “Jelly was always a local star,” Crowell says. “He always had a little more of a glow around him. He’s been a local legend around Nashville since the beginning. He’s been a hero here for a while.”

Jelly Roll was in a dark place, though, during the time he was finding his voice in music. He spent time in and out of jail from the ages of 14 to 24, with charges ranging from drug possession to aggravated robbery. Confined to a jail cell, he used his time wisely: he began to turn his emotions into songs. 

“I wrote more when I was incarcerated than I ever did anywhere else,” he shares. “There is something unique about the situation of being in jail. Everything is stripped from you.” 

His resources reduced to pencil and paper, he eventually went home with a plethora of raps, choruses, and song titles. Then it was back into prison, and during one stretch he started connecting with a new audience: his fellow inmates. 

Every other Friday, the prisoners would host a rap event, and his newfound fans always beckoned him to perform. “I’d always be ready for that, and made sure I had something that went with a topic we can all understand together,” he says. An original song called “Stressed Out” particularly resonated, with lyrics: Talkin’ about being stressed out about the life we live / Just sitting on a bunk wishing we could kiss our kids. 

“It’s something we all felt because there’s the common bond theory of…people connect over common bonds. One common bond in jail is everybody is stressed to maximum capacity,” he explains, recalling how going to court and hearing the possibility of a 20-year sentence was his own top stressor. “I told those kind of stories in song form in there.” 

Flash-forward 15 years from his last jail sentence, and Jelly Roll is now one of the fastest-rising superstars in all of music. Among his many accomplishments: earning his first No. 1 song on country radio with “Son of a Sinner” in 2023; winning New Artist of the Year at the 2023 CMA Awards; and becoming a first-time Grammy nominee in 2024. He was nominated for Best New Artist and Best Country Duo/Group Performance for “Save Me” featuring Lainey Wilson. 

Part of what’s turned Jelly Roll into a superstar is that he doesn’t merely sing about the plight of someone who’s caught in the throes of drug addiction. He’s lived every lyric he writes. This is particularly true of “Nothing Left at All,” “Son of a Sinner,” and “Save Me,” which he cites as the most vulnerable songs in his catalog. 

He wrote “Nothing Left at All” at a time when he was “extremely depressed,” that darkness reflected in such lyrics:  Four in the morning, I cannot sleep / I am depressed, sitting up in my bed / My demons are roarin’, they’re botherin’ me / I’m sitting here with a gun to my head / Finger on trigger, what if I squeezed? / Does that mean that my problems will leave? / Get rid of what’s botherin’ me? / Does that mean that I’m finally free?  

“I wrote this song in a barrel. It felt like where I was at mentally and it’s very reflective,” he says. “That song is extremely powerful to me.” 

He describes “Save Me” as a “cry for help” that also came from an “extremely vulnerable space.” 

“It’s like telling somebody a secret you’ve carried your entire life that’s haunted you every day,” he says of how he feels on the other side of writing such an intense song. “That’s what I said about the anchors of the value of my life—songwriting is that. It’s allowing those thoughts to breathe.”

For Jelly Roll, hip-hop and country have always been linked. He spent as much of his time growing up listening to ’70s country as he did ’90s hip-hop, so it was a natural career move to merge the two genres, which he defines as “autobiographical.” 

Jelly officially made his way into country music with his 2023 debut country album, Whitsitt Chapel. Having watched Crowell’s career skyrocket in country music behind hits from Luke Bryan, Carrie Underwood, Sam Hunt, and many others, Jelly Roll entrusted his longtime friend with co-producing Whitsitt Chapel. Over 30 days, they worked closely together on what would become an acclaimed album featuring back-to-back chart-topping singles (“Save Me” and “Need a Favor”). The record also benefits from collaborations with old friends like Struggle Jennings and Yelawolf. 

“It was always the dream, I just didn’t think I had the voice,” Jelly Roll states of his transition to country music. He says he learned he could sing while recording “Save Me.” “I think a lot of the reason that I did hip-hop for so long was that I didn’t realize that I could sing.” 

Observes Crowell, “It took a while for his musical identity to show up. Once he started singing about the pain and his past that he’s come from, you realize that’s extremely fresh in a genre of music that hasn’t sung about that in a long time, or ever.” 

Crowell also notes how Jelly Roll would oftentimes show up to the studio with unfinished songs and come up with lyrics for them on the spot.“The whole process is extremely honest. The whole thing [went] down unlike the way the rest of the town functions. He’s able to write songs about subject matter that other artists don’t write about.”

Recording “Save Me” introduced Jelly Roll to both the power of his voice and, eventually, the therapeutic power of his words. The singer says he gets inspiring messages “daily” from fans about how his music has impacted them. 

“Knowing how big ‘Save Me’ has been for people in recovery is probably the single most impactful thing,” he marvels. “The saddest stories are always when you meet mothers who play your song at their son or daughter’s funeral. That’s always a really heavy one. To [learn] our song was selected as a way of signifying how this person felt … that somebody deemed it to be played at their funeral. Those are the stories that really resonate with you.” 

Jelly Roll also took his mission to help people in recovery or who are struggling with drug addiction all the way to Congress. He was there to advocate for a bipartisan anti-fentanyl bill, and his powerful testimony quickly racked up more than 3 million views. 

“I’m very conscious of who I’m writing for, and making sure that I know that I’m telling the right story for the little slice of America that allows me to speak for them,” he remarks. “You just make sure you’re writing what you see, or what you know. I never thought that this would be the position I’d be in. I’m very honored, but also very aware and try to be respectful of it, too.”

Part of Jelly Roll’s appeal is the way he’s unapologetically himself. He refers to himself as an “extremely average guy” who’s still learning how to navigate his newfound fame. Crowell can attest to that authenticity. He references the “sweet text” he got from his friend after Whitsitt Chapel was completed and the profound statements he would make during the recording process. 

“At one point he said the phrase, ‘I make broken music for broken people.’ I always gravitated to that, because it’s not polished music. There’s a rawness to it, there’s imperfections. At times, some of the lyrics don’t make perfect sense, but you feel them perfectly,” Crowell reflects. “I did hear him say he wants people to feel music,” Crowell continues. “That’s the number-one thing, he wants them to feel it, and I think he nails that. It’s one thing that he’s always done, is capture a feeling.” 

Jelly Roll is taking his passion back into the studio with Crowell as they work on his next album. “It’s definitely for his people, but he’s growing and his audience is getting bigger,” Crowell says of their approach to the forthcoming release, noting that Jelly is “raising” the bar for his songs. “We’re trying to make music that’s honest to him while keeping his core fanbase happy and fed. We’re trying to make the best art we can.” 

“I can tell you my favorite song I ever wrote in my life is in my phone,” Jelly Roll hints. “I think that this song is so what I do, but so unexpected for me. It’s when a story starts to emerge and the concept and the album start to feel like it means something.” 

Making music that has meaning is a trademark of Jelly Roll’s artistry. The sense of freedom he gets from turning his truth into music is profound, and he’s making it his mission to provide that same feeling of freedom to all who listen. 

“I can remember songs freeing me. I can remember how [Craig Morgan’s] ‘Almost Home’ made me feel when I heard it on the radio in jail,” he reflects. “If I’m able to write a song that affects you in any way that ‘Against the Wind’ by Bob Seger or ‘Fire and Rain’ by James Taylor affects me, I’m honored.” 

One of the many times Jelly Roll got to experience firsthand the feeling his music brings to the masses was when he stood on stage inside Nissan Stadium during the 2023 CMA Fest. Surrounded by thousands of country music fans, he sang his heart out to “Son of a Sinner” and “Need a Favor,” tears welling in his eyes as he stood across the street from the juvenile detention center where he once was locked up. Whether he’s delivering an impassioned acceptance speech at an awards show or sharing a playful (or tearful) video on Instagram, it’s clear Jelly Roll’s gift of connecting with people through music is born from his true spirit.  

“I know the ability that music has to make people feel. I know that in a way that I think a lot of people don’t. I truly understand what it’s like to have a song get you through the death of your best friend, to have a song you remember your son being born to, and what it’s like for these moments to be driven with songs. I get that in a different way. I know more than a lot of people in the city about how music actually makes you feel. When you find a group of people that’s been impacted by the same song the same way, it just resonates different. It’s something about it speaking to the core of our human,” he proclaims. “It’s truly the most powerful vibration on Earth.”

Photos by Andy Pollitt