Jelly Roll isn't shy about his complicated past, and he also opens up to fans about his current personal life.

It's an unexpected success story, but it's the kind that country music loves to share. The name Jelly Roll has only recently become well-known, but many can relate to his challenges.

After a difficult childhood and several stints in jail as a teenager, the Tennessee native found the motivation to improve himself and pursue his dreams, which ultimately led him to fame.

At the 2024 CMT Music Awards, Jelly achieved a remarkable feat at the star-studded event held at the Moody Center in Austin, Texas, winning Male Video of the Year, CMT Performance of the Year, and the top honor, Video of the Year.

This marked his second consecutive year of sweeping the awards. "I don't know what to say. I'm out of words.

By the last time I got up there, I was like, 'Man, this is crazy,'" the "Need a Favor" artist shared with ET backstage. "It's just unreal, man."

This came after he won the New Artist of the Year award at the 2023 CMA Awards and received two GRAMMY nominations, including the prestigious all-genre Best New Artist category, at the 2024 ceremony.

The fact that he didn't take home a golden gramophone in February is hardly a concern for him.

"Being recognized by the [Recording] Academy and being here to represent Nashville and country music, as well as my slice of America that often goes unheard, means a lot.

There are many people who have never been represented, and they are represented here tonight," Jelly expressed to ET on the GRAMMYs red carpet.

"We didn't come to win; we came to represent, baby!" Here's a look back at the winding journey that took Jelly Roll from a troubled teenager to a country music sensation.

EARLY STRUGGLES

Born Jason Bradley DeFord in Nashville in 1984, a tumultuous upbringing led Jelly Roll to a life of crime at an early age.

A guard knocked on my cell door one afternoon during lockdown," Jelly recalled in an interview with Billboard last year.

"He said, 'You had a kid today.' In that moment, I felt a strong urge to change my life. I knew I had to figure things out right then and there."

The birth of his daughter, Bailee, in 2008 shifted the singer's perspective, prompting him to pursue his GED to improve himself. "I spent less than 60 to 70 days in high school.

I thought I was a real dumbass. I believed I had a learning disability," he shared, noting that he passed his exam on the first attempt. "I walked in there and knocked it out of the park."

He first ventured into the music industry in 2003, starting with hip-hop and releasing The Plain Shmear Tape. After a series of collaborations, mixtapes, and further stints in jail, Jelly transitioned to rock and country music, eventually performing on the Grand Ole Opry stage in November 2021. 

I cried like a baby in front of 12 strangers. I had just signed my record deal, so I didn't even know my record label yet, he remembered about the moment before his fourth performance in April 2023.

"But that was part of why I signed my record deal – I had two conditions. I told them, 'You have to promise me you'll get me in the local newspaper, and you have to promise me you’ll get me to the Grand Ole Opry.'

I just wanted to prove that I am who I say I am, even if they never bring me back. That's fine. Just let me be the guy who gets to do it."