Jelly Roll talks 'second chances' after growing up in and out of prison: 'Nothing I am prouder of'

Jelly Roll is well aware and grateful of the second chance at life he has gotten.

The "I Am Not Okay" singer has come a long way from his difficult childhood and early adult years spent in and out of jail, and these days his focus is his family, career, and leading a healthy life.

Plus, now he is also focused on passing on some of the luck he got when it came to turning his life around.

Speaking with People about designing and launching his own shoe with HEYDUDES, Jelly first reflected: "From who I represent and the people I represent in America, also even in country music, to being one of the first country artists with my own shoe… I don't know man, it’s just cool and it could have happened with anybody."

The rapper, whose real name is Jason Bradley DeFord, was born in Antioch, Tennessee in 1984, and has spoken candidly about his prison record. He 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. 

Further discussing how the new shoes represent him, he said: "It's Jelly Roll all over the shoes — redemption, second chances, self-belief, faith, family. I stand on everything I stand for when I wear these shoes."

"I think second chances are earned," Jelly went on, adding: "I think sometimes you can earn them in opportunity — there are opportunities to earn — but I believe that second chances are earned."

He's still sometimes in disbelief over the opportunities he has earned. "There are so many experiences that in real time you can't quite even believe they are happening because how can you believe that you're at this show or talking to this person," he said.

"But if you're asking me what I am most proud of, it's going back to see the kids at the juvenile and being able to visit with different facilities across the country and now internationally when I am touring and hearing the stories of those that feel like they may not feel represented all the time," Jelly further shared.

Last year, 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.

Now, he takes his new privilege seriously. "Being able to speak on a real level with someone about how they are one good decision from changing their life and being on track is something that I don't take for granted that I get the opportunity to do."

"Showcasing that second chances are possible? There is nothing I am prouder of," he added, maintaining: "And I want to continue to be an example of that."