The country star opens up to PEOPLE about raising his daughter Bailee, 16 Jelly Roll was just 14 years old the first time he was arrested — but he’s not worried that his teenage daughter Bailee will make his same mistakes.

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,

"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.