Why did Jelly Roll spend years in prison? All he's said about his arrests and felony | HELLO! (2024)

It has been a long, complicated journey for Jelly Roll to become the award-winning country singer that he is today.

The "Son of a Sinner" singer, whose real name is Jason Bradley DeFord, was born in Antioch, Tennessee in 1984, and before he was mingling with stars at award shows, he was in and out of prison for much of his teenage years.

The country star has since transformed his life — with the loving support of his wife Alyssa "Bunnie XO" DeFord, who he married in 2016 — and has spoken candidly about his previous troubles with the law, in addition to becoming a drug prevention activist. Here's what to know.

Childhood

Growing up, Jelly Roll's father worked as a meat dealer and bookie, while his mom, who was the one to first nickname him Jelly, struggled with mental illness and addiction.

During an interview with CBS News in which he visited his old jail cell at the Metro-Davidson County Detention Facility in Nashville, he admitted he never pictured himself as a singer despite his love for music, and shared: "I knew my father booked bets. I knew my mother struggled with drugs. So, to me, this was just what you did," referring to when he worked as a drug dealer.

Still, he worked on his music even then, and further recalled: "I'm just like, 'Yo, here's a sack of weed. Here's a gram of co*ke. Here's a mixtape.' Know what I'm saying? 'I rap, too!' It was like my business card. Even my drug dealing, to me, was always a means to music."

Why did Jelly Roll go to jail?

Jelly Roll first went to jail when he was 14, and spent the next almost ten years in and out of facilities — he's said he's been arrested around 40 times — for charges relating to drug possession, drug dealing, shoplifting, and aggravated robbery.

"There was a time in my life where I truly thought this was it," he said during his CBS News interview.

What was Jelly Roll's felony?

When he was 16, Jelly Roll was arrested for aggravated robbery and charged as an adult after he was part of a robbery with a gun over weed. "I never want to overlook the fact that it was a heinous crime," he told Billboard, adding: "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."

He was sentenced to eight years in prison and seven years of probation, and though he only served just over a year for the charge, the felony conviction has had long-lasting consequences.

Because of Tennessee's zero-tolerance policy for violent offenders, the charge is still on his record, therefore he cannot vote, and until recently, he couldn't get a passport and travel internationally.

He told Billboard it also got in the way of him being able to buy a home he wanted in a gated community with its own private golf course. "Imagine changing your life in such a way that you can afford the kind of house in this community I was looking at," he said. "My money was welcome, but I wasn’t, all because of something I did [almost] 24 years ago."

Post-Prison Life

When he was 23, on the day he was last released from prison in 2008, Jelly Roll learned he had fathered a daughter, Bailee Ann, who he met on her second birthday, and is raising along with his wife Bunnie. The couple has full custody of the 16-year-old, and they also co-parent son Noah, seven, with a previous partner of the doting dad.

In November of 2022, he donated over $200,000 to the Davidson County Juvenile Detention Center, where he spent time as a teen, for the construction of a music studio.

In January of this year, he also delivered powerful testimony before Congress in support of anti-fentanyl legislation. "I was a part of the problem. I am here now, standing as a man that wants to be a part of the solution," he said.