From Prison to No. 1 Song: Jelly Roll’s Unlikely Rise to Country Music Stardom

Born in Antioch, Tennessee, in 1984, Jason Bradley DeFord had a rough start. He was the child of a drug-dependent mother and a bookie father. Few who knew him as a young rapper constantly in trouble with the law would imagine he'd become Jelly Roll, a chart-topping country artist who took the world by storm with his 2022 single "Son of a Sinner." Let's look back on Jelly Roll's remarkable journey from prisoner to Billboard chart topper and the bright future that lies ahead.

Most teens focus on keeping their grades up, finding their place in the social hierarchy, and navigating crushes. For young Jason, or Jelly as his mother called him, 14 marked his first of many arrests. He spent his 15th birthday behind bars, starting a trend that would continue for the next five years. Among his worst offenses were two counts of aggravated robbery at just 16. He faced a 20-year sentence but served just over a year, yet it wasn't enough to scare him straight.

Jelly Roll was incarcerated 40 times and missed many important events, including the birth of his daughter, Bailee, while he was serving time for drug dealing in 2008. He told Billboard that her birth was a turning point, noting, "I've never had nothing in life that urged me in the moment to know that I had to do something different. I have to figure this out right now." And figure it out he did, mending his ways and focusing on being a good father.

Rap was a part of Jelly's life throughout his struggles with the law. He made hip-hop mix tapes, which he'd give to the people he dealt drugs to. He wrote hundreds of songs while incarcerated and launched his rap career when he left jail for the last time. His 2010 rap single, "Pop Another Pill," was a minor hit, but he struggled to break through.

That was until 2020, when his acoustic version of a song called "Save Me" went viral. The next year, Jelly performed at the Grand Ole Opry, cementing his transition from rap to country music.

Jelly Roll got his first taste of major success with the release of "Son of a Sinner" in 2022. It reached No. 8 on Billboard's Hot Country Songs chart and topped the Country Airplay charts. The enthusiasm of fans played a key part in the song's radio success. Atlanta program director Mike Moore said several listeners called into his station to request "Son of a Sinner."

But it wasn't just the country world that fell for this No. 1 song. "Son of a Sinner" also reached No. 31 on the Billboard Hot 100, proving his cross-genre appeal.

On his Facebook page, Jelly Roll explained the meaning of "Son of a Sinner," noting that "It is about the duality of life, and we all go through it. Sometimes we are all just a little right and wrong." He brings that duality to life through the story of a recovering addict who's always "one drink away from the devil." Listening to the opening verse, where the narrator is on a lonely highway, it's easy to see why Jelly Roll, a touring musician, told Billboard that some parts of the song are "extremely autobiographical."

The positive reception to "Son of a Sinner" helped open doors for Jelly Roll. The opportunities it brought set the stage for his future success.

Jelly Roll isn't your typical country music success story. His underprivileged childhood, face tattoos, and willingness to experiment with genres help set him apart from his contemporaries in the genre. Few other country acts would collaborate with rappers such as Shaboozey, Eminem, and Machine Gun Kelly or pop artists such as Alex Warren and Jessie Murph, but Jelly seems to relish the challenge.

Walking his own path hasn't hurt Jelly Roll's career. The Country Music Association named him the Best New Artist in 2023. He took home three trophies at the CMT Music Awards in 2023 and 2024. He also beat out acts such as Linkin Park and Superheaven when "All My Life" was named Top Hard Rock Song at the 2024 Billboard Music Awards. He's also sold out prestigious venues, including Nashville's Ryman Auditorium and Bridgestone Arena. As the country world embraces this unlikely star, Jelly Roll is opening doors for other artists who don't fit the mold.

Jelly Roll aims to pay it forward and help others in need. He's passionate about reforming the criminal justice system and supporting those impacted by incarceration. Believing in the healing power of music, in 2022, he donated $250,000 to build a recording studio in the Davidson County Juvenile Detention Center, where he spent time as a troubled teen. The money would also help fund scholarships for graduating teens and provide holiday food and toys for local families in need.

Having seen the impact of drugs first-hand, in 2024, Jelly Roll testified before Congress, urging them to pass antifentanyl trafficking laws. In 2025, he became the co-chair of the Mobilize Recovery Campus Surge 2025 Initiative. The program aims to help students access treatment options and mental health support as they navigate sobriety.

In 2024, Jelly Roll released his latest album, Beautifully Broken. It became his first No. 1 album, showing that there's no slowing down this juggernaut. His U.S. tour with Post Malone, the "BIG ASS Stadium Tour," called the "BIG ASS World Tour" for their shows in Europe, make 2025 a year to remember. With so many opportunities in the United States and abroad, such as Canada's YQM Country Fest, Germany's Superbloom Festival, and Mexico's Corona Capital Festival, the future looks bright for Jelly Roll.

Jelly Roll's story proves that no matter how low you fall, it's possible with perseverance to rise again. His trajectory serves as an inspiration for anyone who's hit rock bottom. Through music, Jelly Roll has managed to transform his life and make a contribution that's more positive than he may ever have imagined. He's already made a massive impact on the country music scene, but his upward trajectory suggests he has the power to continue breaking barriers and making his mark.