Cross-genre artist, Jelly Roll, has come a long way since his days behind bars. Now, 15 Hip-Hop albums deep, celebrating multiple #1’s in Country Radio and recently charting Top 40 on Pop radio, the 38-year-old is ready to take this thing international.

“I’m starting to scare myself with my dreams now,” he told Audacy’s Rob + Holly, admitting he never would have been “bold enough” to dream this big in his troubled younger years.

“I’m shooting for the moon now — Madison Square Garden, baby” he exclaimed. “Man, I wanna go play the O2 Arena in London. I’m havin’ international dreams. I wanna go see the world. I wanna go see Egypt, I wanna go to Dubai. I want to take this thing everywhere, dude. I want to go to Italy, I want to eat pizza and ride on one of the little boats. I’m having dreams I never even thought was possible.”

The Nashville native has always been open with fans surrounding his troubled past including his struggles with addiction and the legal system. Instead of hiding from his truth, Jelly has boldly stepped up to to inspire, connect and educate fans all over. “I think my message to people is simply, ‘believe and dream,’” he shared. “I think at some points it wasn’t a belief that this thing was going to work for me, I think it was almost stupidity. At some point it was almost delusional, I bet people thought.”

There’s nothing “delusional” about Jelly’s success now… according to his wife, Bunnie, the only thing delusional about him was his thinking his hairstyle looked good before getting it cut last week. Jelly recently wow’d his fans with a clean cut after sporting long, mullet-style locks for the past several months, a look his wife was vocal about disliking.

“I finally cut it,” he told Rob + Holly while showing off the new look. “My wife had been telling me to cut it for six months, and you know how we are with the person we trust the most in our life— we think they’re bein’ a hater,” he laughed.

“It’s like, ‘I trust you with my life, my children, my finances, but you don’t have an opinion on my hair,’” he continued. “And then you cut your hair and you’re like, ‘why did nobody tell me I was lookin’ unkept?’ I was out here on red carpets wearin’ baseball caps lookin’ homeless.”

Never a dull moment when Jelly Roll is around. Check out his entire interview with Rob + Holly above to hear more about his big dreams, most successful night at the casino, plans for the future, and more.

Words by Monica Rivera Interview by Rob + Holly