Jelly Roll is opening up about an emotional conversation he had with his 16-year-old daughter Bailee who is now the same age he was during his struggles as a teen.

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,

Despite his own troubled adolescence, Jelly Roll noted that he feels confident in Bailee's future, saying that she is "ahead" of where he was at 16. While he sometimes pushes her, he assures that it's from a place of love and concern.

"Lonely Road" singer Jelly Roll—who got arrested at age 14—shared insight into difficult conversations he's had with his 16-year-old daughter, Bailee, about his past.