How Jelly Roll's Music Career Started While He Was In Prison

It's undeniable that Grammy-nominated singer Jelly Roll has led a tumultuous life. The singer, whose real name is Jason Bradley DeFord, has been incarcerated numerous times since he was a teen for crimes related to drug dealing and, when he was 16, for aggravated robbery. Luckily, the birth of his daughter Bailee Ann in 2008 while he was imprisoned inspired him to change his lifestyle, and the rest is history.

While serving time in various jails and prisons obviously wasn't great, it did give Jelly Roll time to focus on writing songs — and he took advantage of it. The singer told guest host Martin Short on "Jimmy Kimmel Live" that he had started composing his own songs as a kid, influenced by his mom's love of music. "In jail is where I really started [writing music]," Jelly Roll said. "I had a lot of time. A lot of time. I was like, 'Maybe I should invest this time in something positive.'"

Short seemed intrigued by how Jelly Roll managed to write music while incarcerated, especially when Jelly Roll said that it took unconventional means to actually craft a melody. "We wouldn't have an instrument, so we would have to make them on the table," he said. When the "Father of the Bride" actor asked what that meant, Jelly Roll gave him a personalized demonstration.

While appearing on "Jimmy Kimmel Live," Jelly Roll demonstrated how he crafted the beats for songs while in jail by pounding out a rhythm on a table and snapping his fingers. He even wrote an impromptu rhyme for guest host Martin Short and fellow guest and "Glee" star Jane Lynch, much to the actors' delight. "I can't believe I'm doing this / I'm sitting by your side / I can't believe I'm sitting with the / Father of the Bride ... Hey, that's crazy to me / I'm in between Martin Short and the lady from 'Glee'," Jelly Roll rapped.

Jelly Roll's talk-show appearance is just another piece of evidence showing what makes him so relatable as an artist — his willingness to share his tragic life story and his gratefulness for getting to where he is today. In June 2024, he and Ashley McBryde hosted the summer concert special CMA Fest, which aired on Hulu in June 2024. It was another surreal moment for the "Halfway to Hell" singer due to the location of the show in Nashville, not far from the Davidson County Juvenile Justice Center. "The magnitude of the moment really hit me, to be across the street from the juvenile detention center I was in and to now be onstage hosting," Jelly Roll said (via CT40). "how do you describe being in the same exact place while being in a place that couldn't be more different, at the same time?"

These days, Jelly Roll has transcended his past and the accolades are piling up. The "Wild Ones" singer received two nominations at the 66th Annual Grammy Awards for Best New Artist for his album "Whitsitt Chapel" and Best Country Duo/Group Performance for the remix of his song "Save Me" with singer Lainey Wilson. In April 2024, he collected three trophies for "Need a Favor," including Video of the Year, and had won three more the year before for "Son of a Sinner." 

The singer also experienced a life-affirming moment when one of his idols, Eminem, sampled Jelly Roll's song "Save Me" on his 2024 album "The Death of Slim Shady." Jelly Roll shared his joy about the situation on Instagram. "As a teenager (and still today) I could recite every song on the Slim Shady album, the Marshal Mathers album, and the Eminem show," Jelly Roll wrote alongside a picture of himself with the "Houdini" singer. "I related to every word Eminem wrote. ... for him to use the song to discuss the other side of what could've happened if he would've allowed his demons to win brought me to tears." We can only imagine how special the moment must've been for Jelly Roll, and it's super sweet that he still gets starstruck — just like he did when he met singer Gwen Stefani.

Jelly Roll has also proven that he's willing to give back to those in need. In 2023, he performed for inmates at a jail where he himself once served time. The singer has created scholarships for college-bound students in Davidson County, Tennessee, and also planned to fund a recording studio in that same juvenile detention center where he was incarcerated.