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Struggle Jennings on Grandpa Waylon Jennings’ Legacy and Return to Music After a Prison Sentence

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Struggle Jennings has been through hell and back — but he’s not going to let his past define him. Instead, he hopes to share it through his music and help someone in need.

Jennings’ newest record Monte Carlo, out Friday, shows the musician in a new light as he opens up about his dark past and journey to finding light.

“A lot of people told me, ‘Man, calling yourself Struggle, you’re going to go through a lot of struggles,’ And I was like, ‘Yeah, but if I can overcome them, then I own that name,’” Jennings, 42, tells PEOPLE exclusively.

He adds, “‘And I give people hope that regardless what they’ve been through, their past doesn’t have to define them.’ I always say, ‘Don’t let your past define you, make it refine you. Make it make you better.’”

The record — named after the nostalgia that his ’84 Monte Carlo brings him — has a touch of the ’80s, hip-hop and rap, though this is the first time that Jennings ventures into country music.

“I love country music. It’s part of my history, and my background, and the backdrop of my childhood,” he says. “So ‘Monte Carlo,’ the song and the album is that bridge where it’s the best of both worlds.”

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Writing this album was a healing process for him, as it touches on personal subjects like the murder of his father, his five-year prison sentence from 2011-2016 on drug charges and losing the mother of his children to an overdose.

“I was just fed up with all these people making bad decisions and us having to lose family members to addiction and poor choices,” he confesses.

“Every time I would start listening to it, I would just break down. Watching my kids go through what they went through, losing their mother and feeling the weight of that,” the father of seven continues. “And me not really being able to protect them from it, only be there for comfort and support, but not being able to fix it. As a father, that was really hard.”

He adds, “But it was such a relief and I got that off my chest. I was able to express myself through a song that’ll hopefully help somebody else who’s going through the same thing.”

 

When asked what it was like coming back to his life after spending five years in prison, the singer says that it certainly wasn’t easy — but time made him realize what was most important, like his friendship with country singer and rapper Jelly Roll.

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“It was difficult, but I knew what I wanted and I knew what I was going to do. I sat in prison and I realized when I got there that I had lost complete control of everything on the outside of those walls. My family was going through terrible things. My money was disappearing,” he says.

“Everything that I had built was pretty much crumbling and I couldn’t control that. I had incredible friends that would stop through and help out any way they could. At one point, Jelly Roll had my kids. But I’ve realized the only thing that I could control was me, and who I became, and how I let that time affect me and who I was going to be when I came home,” he concludes.

Now, Jennings is focused on the future. He has a 50-date tour with Jelly Roll that kicks off in June and he’s hard at work in the studio.

Jennings — who used to simply go by “Struggle” — has also learned to embrace his last name and honor Waylon’s legacy.

“The quote that Waylon had was like, ‘Don’t stand in my shadow, find your own light.’ And that’s something that I’ve tried to do,” he says. “[But I’m] paying homage to the man. My dad was murdered when I was 10, and Waylon stepped up and was a father figure in my life. He was the only real male role model I had besides my uncle on my dad’s side that ended up getting custody of me when I was young.”

He continues, “But Waylon was one of the biggest male influencers in my life. He taught me about family, he taught me about standing your ground, sticking to your guns, he taught me what being a man is.”

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