When he was just 23 years old, country music star Jelly Roll served time behind bars after being convicted of drug dealing. At the time, he was expecting his first child with then-girlfriend, Felicia Beckwith.

Jelly Roll, whose real name is Jason DeFord, was in jail when Bailee Ann was born. When he was released, he had a 2-year-old who barely knew him — and he had to work to build a relationship with her.

“I got home when she was almost 2,” he said on the Monday, March 3 episode of the SmartLess podcast. “Her mother, at the time, because I was rightfully so a [expletive] criminal, wouldn’t let me see her. So I had to go to court. I had to get supervised visits through the courtroom.”

“I had to step that very slow, build a relationship, then six hours on Friday evening, but she had to be home before 10 p.m. I just had to keep going to the court every six months and going, ‘Look, I’m continuing to prove I’m changing.’ Music, like being famous, wasn’t even a thought then. I just wanted to be a good dad,” he added.

Jelly Roll’s legal issues started when he was just a teen. At the age of 16, he was arrested for aggravated robbery — and charged as an adult. The aftermath of that arrest is still haunting him today.

“They were talking about giving me more time than I’d been alive,” he told Billboard in June 2023. “I hadn’t hit my last growth spurt. I was charged as an adult years before I could buy a beer, lease an apartment, get a pack of cigarettes … I feel like the justice system at that point kind of parked me on my only set path.”

Jelly Roll and Bailee Ann are extremely close. In 2020, the two collaborated on the song Tears Could Talk, and the teen appeared in the music video.

“Proud dad moment today…She wrote this verse all by herself , and getting to share her story and shoot this video means so much to me I am getting emotional just typing this post,” he captioned an Instagram post in March of that year.

These days, Bailee Ann, 17, lives with her dad and his wife, Bunnie XO (whose real name is Alyssa DeFord). Jelly Roll is also a dad to son Noah, 8, whose mom’s name is Melisa Cowell.