Jelly Roll has never been shy about his long, hard road to stardom, which included multiple run-ins with the law as a teenager and twentysomething that landed him behind bars. But now that he’s on the straight-and-narrow path and has catapulted from juvenile delinquent to chart-topping global country superstar, the 39-year-old singer told People magazine that he’s making sure his 16-year-old daughter Bailee doesn’t hit the same roadblocks he did when he was her age.

“[I said], ‘I don’t judge you based on what you do. I judge you based on what I know you’re capable of,’” he said of a recent chat he had with his daughter in which he reminded Bailee of how much potential he sees in her in the cover story titled “From Inmate to Icon: How Jelly Roll Beat the Odds.”

“‘You’re so much smarter than I was at 16. You’re so much better, so much more emotionally intelligent,’” he said he told his daughter, who was born in 2008 when he was in prison. “‘You can read a room so much better. So don’t try to talk your way out of getting in trouble, Miss Sassy, by weaponizing my past,’” added the “Save Me” singer who was 14 the first time he got arrested. Jelly and wife Bunnie XO have had full custody of Bailee since 2017 because of her biological mother’s reported substance use struggles.

The good news for the father of two — he also has an eight-year-old son named Noah — is that he thinks Bailee is “totally ahead” of where he was at her age, confident that she has a promising future. “When I look at what she does that I consider horrible, I look back at what I was doing at 16, and I’m like, ‘Oh man…’ When I’m hard on her about stuff or a little pushy, she knows it’s from love,” he said.

As proof, Bailee was with Jelly when he performed at last week’s 2024 CMA Awards. “We were really, really close before it exploded, but she understands what it’s doing for her future and the family’s future,” he said of the path the father-daughter relationship has taken as his career has gone supernova over the past two years. “She’s a really hammered down kid. She’s been in the same public school district for 10 years and had the same friends since me and Bunnie have had custody of her. I think a lot of that has helped.” In a recent appearance on Bunnie’s Dumb Blonde podcast, Bailee said she hopes to attend Columbia University to study criminal law after high school.

The six-time country Airplay chart-topper closed out his Beautifully Broken arena tour at Nashville’s Bridgestone Arena on Tuesday night (Nov. 26) where he was joined by guests including Snoop Dogg, ERNEST, Morgan Wallen, Keith Urban and Skylar Grey. He is slated to support Post Malone on the singer’s 2025 Big Ass Stadium Tour next spring.