Struggle Jennings Praises His Grandfather, Waylon, As ‘Monte Carlo’ Is Out

Struggle Jennings‘ latest album, Monte Carlo, is out now. The record is a testament to how far Jennings has come, including a five-year incarceration on drug charges, and overcoming addiction that already claimed the lives of those close to him. It’s an uphill battle that Jennings says would not have happened without the influence of his grandfather, Waylon Jennings, and the hands-on support of his good friend, Jelly Roll.

“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,” Jennings tells People. “[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.”

Jennings’ life could have — and likely would have — turned out entirely differently, if not for Waylon taking on an active role in his grandson’s life.

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

It was while he was in prison that Jennings realized he was at a crossroads, vowing to do whatever he could to make sure the trajectory of his life changed. It was a sobering wake-up call, which required the help of Jelly Roll, who understood all too well the challenges Jennings was facing.

“It was difficult, but I knew what I wanted and I knew what I was going to do,” Jennings recalls. “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.”

“Everything that I had built was pretty much crumbling and I couldn’t control that,” he adds. “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,”

All of the songs on Monte Carlo in some way touch on Jennings’ path, becoming a story of redemption that touches on the myriad of emotions he has experienced over the past several years.

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

“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.”

Jennings at one time wanted to be known for his own music, not as part of country music royalty. But now, the singer-songwriter is honored to carry on a name that has become iconic within the genre.

“I don’t really feel the pressure anymore,” he tells Everything Nash. “Of course at first I did, but I had to create my own path. There were definitely no doors opened because of that name. If anything, a lot of time there’s a stigma that comes with the name. And what I was doing was so outside of the box of country, I didn’t get any love because of that name. Of course, through relationships I did, but there was no like, ‘Oh, he’s Waylon Jennings’ grandson, let’s bring him in and give him a record deal.’ There was nothing like that.”

Jennings will serve as the opening act for Jelly Roll’s Backroad Baptism Tour this year. Find Monte Carlo and all of Jennings’ music and upcoming shows at