“When I went to prison this last time, I lost everything,” Struggle Jennings told American Songwriter. “I watched the mother of my children get addicted to drugs and eventually die from an overdose, I watched my kids go into state custody. Seeing all of the heartache and terrible things they were going through really gave me the motivation to come out and be the best father, man and artist that I could be.”
And in 2016 when he got out of prison, Jennings did just that—in the years since, he’s released a plethora of charting hip-hop albums, won back custody of all of his children and has entirely rebuilt his life through perseverance, talent and honesty. Frequently collaborating with longtime friends like Jelly Roll and Yelawolf, Jennings and his music have become beacons of hope and inspiration for many, sharing a message of clarity, stability and healing with those who need it the most. In late 2020, Jennings and Jelly Roll released their fourth joint-record to date, Waylon & Willie IV, which serves as a testament to the tremendous growth Jennings has undertaken in the past four years.
Yet, the feat of Jennings’ growth was no small task—his life has been true to his first name. Born in Nashville in 1980 to Jennifer Eddy, the daughter of Jessi Colter and Duane Eddy, and raised in the shadow of his step-grandfather, Waylon Jennings (who married Colter in 1969), Struggle Jennings became acquainted with hard-living at an early age.
“My mother decided that she didn’t really want to live off Waylon’s name or really take any handouts,” he explained. “She also had a thing for ‘bad boys’ and always dated guys who were a bit rough around the edges—my father and a series of guys after that being examples. So, I went through a lot throughout my upbringing—especially after my father was killed when I was 10.”
After the death of his father, Jennings found himself in a tough spot and, ultimately, began making decisions he would later regret. “Before my dad died, I spent my weekends on the west side of Nashville,” he said. “In the summertime, I went to the hood. After that, when I got a little older, my mother wanted to make it on her own, so we moved to lower-class, low-income housing. From then on, I was engulfed in that culture. It was just who I was.”
From there, one thing led to another and Jennings ended up having several run-ins with the law, eventually getting sentenced to prison in 2011 and serving until 2016. In the years before that fateful sentence, Jennings faced severe hardship that would’ve been unbearable had it not been for one source of solace and strength: music.
“Well, I had a connection with hip-hop immediately,” he said. “Of course, I come from a family where my grandfather sang country, but my mother had me in 1980 when she was only 16 years old, so she was listening to what was popular then. I really grew up on ‘80s and ‘90s music as it was being made—whatever was ‘hot’ at that moment was what my mother was listening to. The first record ever that I remember getting was N.W.A. Then, the first record I remember actually buying for myself was Dr. Dre’s The Chronic. So, I grew up to that. I remember a friend of mine brought me a 2 Live Crew cassette—he snuck it to me, it was music that talked about shit we weren’t supposed to know as 8-year-olds. But, that was just kinda the era. I related to the stories that were being told in hip-hop.”
For Jennings, this early love for hip-hop came hand-in-hand with a desire to create music himself. “I started writing poems when I was super young,” he remembered. “When I was growing up, my mother was always in the living room, playing piano and writing songs. So, I always felt it calling me. I first started writing poems around when I was 8 years old. While I’ve been singing for as long as I can remember—I was one of those kids who just walked around singing all the time—I was probably about 12 or 13 when I realized ‘Hey, I want to be a rapper.’ But, I didn’t really take it seriously until I was in my early 20s.”
Even though Jennings was pursuing music, he now realizes that he was still on a bad track. While there are many socioeconomic factors contributing to the ongoing crises plaguing low-income Americans—and the criminal justice system tends to exasperate, not alleviate, those issues—Jennings’ own struggles partly stemmed from an unsupportive environment; an environment in-which the wrong things were glorified for the wrong reasons. Jennings remembered this all throughout his prison years, so it’s no surprise that once he got out he devoted himself to crafting music that was as raw and honest as possible.
“My music has to be honest” he explained. “I owe it to, not only the listener, but to my children. I owe it to my family because of all of the heartache caused by beliefs we were taught as kids. You know, stuff like ‘Feed your family by any means’ and ‘It’s okay to do wrong as long as you’re doing it for the right reasons.’ Those beliefs were instilled in us as kids, a lot of times through music and entertainment. The streets had been glorified and I fell right into it. I was blinded by the glitter of diamonds, cocaine, money, women, cars and rims. Now, I have an incredible wife and a beautiful car with rims, but I’m getting it the right way. So, I try to be honest and tell both sides—yeah, I was having fun back then and making money, but I didn’t get to keep any of it. They kicked my door off the hinges and took everything I owned.”
This is a lesson that was also learned by Jennings’ grandfather, Waylon, when he was arrested in 1977 on federal drug charges. In fact—shortly before he began to serve his prison sentence, Struggle began to embrace his heritage for the first time since his mother broke free to make it on her own all of those years ago. Donning the name “Struggle Jennings,” he worked up an incredibly moving tune built around a sample from his grandpa’s famous “Don’t You Think This Outlaw Bit’s Done Got Out of Hand?” The resulting track—“Outlaw”—served as the first of a long line of powerful songs from the younger Jennings.
“When I was first really embracing who I was and the kind of music I wanted to make, I knew that I couldn’t glorify anything I had done in the past or that type of lifestyle and its repercussions,” he explained. “That lifestyle does have repercussions—I’ve felt them, my family has felt them. I’ve buried 40 of my closest friends because of gang violence, robberies, drug violence, overdoses. If I were to be dishonest and go out there and glorify that lifestyle, they’d be dying in vain. I can’t glorify it. I would rather sell 1,000 records and save 10 lives by being honest than go platinum and ruin even one life by inspiring someone to live the lie I was telling in my music.”
This drive—this unwavering desire for self-betterment—was not only a huge source of Jennings’ strength as he navigated the transition from prison life back into family life, but it was also the underlying motivation behind Jennings’ collaboration with fellow Southern rapper, Jelly Roll. Right after Jennings got out of prison in 2016, he and Jelly Roll got into the studio together and began cutting tracks for what would ultimately become the first volume of their Waylon & Willie series. Friends for decades, their mutual backgrounds and mutual search for balance in life forged an unbreakable bond.
“Everything that two men can possibly go through together, me and Jelly Roll have gone through together,” Jennings explained. “We’ve carried caskets, we’ve taken care of each other through jail and prison bids, we were on the streets together when music wasn’t on the up-and-up and we were hustling. We’re best friends. That’s actually where the idea for the Waylon & Willie series came from, our friendship. Willie was the light-hearted one, Waylon was the rough-around-the-edges outlaw. Plus, Jelly smokes a lot of weed, like Willie. So, we called it Waylon & Willie as a tribute to that friendship. The first one was incredible and we had a lot of fun with it, the second one was even more fun and ended up even better. The third one was great too and now we just put out the fourth. It’s something that he and I are really good at doing together. We did three in one year, but now that it’s all kinda blowing up, it’s looking like we’re settling into one a year. We take everything we’ve been through the whole year—we’ve got our own families, our own careers, our own things going on—and we’ll lock-in for two weeks and let it all out through music.”
When listening to Waylon & Willie IV, the confessional, cathartic nature of the music becomes evident. With powerful lyrics addressing everything from depression to addiction to suicide to finding hope, the two men lay bare their souls, all for the purpose of establishing a holistic source of strength and understanding. Both Jennings and Jelly Roll confess that being so candid on record has been scary at times, but, ultimately, the reaction from the community has been so overwhelmingly positive that they can never go back to the way it was before.
“It’s always a little frightening when you put yourself out there in such an honest way,” Jelly Roll admitted. “‘Acceptance’ is such a big word. When we were kids, all we ever wanted was to be accepted. But, I was in the ‘unaccepted’ group, the outlaw, misfit group. So was Struggle. I think that when we started to wear that on our sleeves openly, that’s when things started to open up for us. We realized that there are so many people who feel the exact same way we feel. So, it goes from being kinda scary to realizing that you’re not alone. So many people find strength in this. You can show other people that they’re not alone because of what you do, the music you make and the messages it sends. On this record, I think the most insane line I said about myself was: With depression, we all deal with it different/ as for me, it’s obesity and alcoholism. I’m being honest, I’m saying ‘We all deal with this stuff one way or another, this is just the way I deal with mine.’ People appreciate the integrity, the vulnerability. There’s a saying: ‘Legends are made from vulnerable men.’ I truly believe that.”
If we take this saying at face value, then both Jennings and Jelly Roll are prime nominees for “legend” status. All in all, the life Jennings has lived would be more than enough excuse to succumb to the chaotic currents of the world, but his determination to control his own future shows us who he really is: a strong, principled, humble and loving individual.
“When I got home, I was fighting to get my kids back as a three-time felon,” he said. “They said jobs are hard to get, they said ‘Oh, well you can’t do this because of that.’ To be able to break away from all of those stereotypes and restrictions and be successful, to make it and provide for my family, to get custody back of all of my kids, to stay out of prison and off of drugs, being able to show people that that’s possible… it keeps me grounded. It keeps me from going back. I think about the people who’ve said that my music inspired them to change their lives, to be a better man, father or husband, to work harder, to chase their dream, to understand that they don’t have to go back to prison, they don’t have to continue to use drugs or fall into these same cycles that their families have been trapped in. In a way, it gives me a responsibility—people are watching me, people are looking to me for strength, guidance and a glimmer of hope. Music can save lives—it’s definitely one of the things that saved mine—so, it’s an honor to share that.”
Watch the music video for “Enemy” by Struggle Jennings and Jelly Roll below:
Photos by Alectra Busey