Struggle Jennings on Redemption, Outlaw Hip Hop, and Turning Pain Into Purpose

As a part of our interview series with leaders, stars, and rising stars in the music industry, we had the distinct pleasure of interviewing Struggle Jennings.

The grandson of Waylon Jennings and Jessie Colter has been nothing short of a true Outlaw from a long line of gangsters, outlaws, and rockstars, making his family lineage proud. An RIAA Certified Gold-selling artist for his collab with Jelly Roll on Fall In The Fall, and #1 Billboard Charting artist for “God We Need You Now”. Struggle has revolutionized a new style of music, blending Country and rap influences and making ground-breaking country rap styles. Contrary to his family’s upbringing, Struggle and his single mom grew up in low-income housing, and being the black sheep of the family, he fought through the streets of West Nashville and into the studio where he would create the foundation for what has become his contribution to the Jenning’s family legacy. Struggle’s message of strength, determination, and courage in the face of adversity continue to connect and resonate with people around- the -world. By sharing his story with honesty and passion he has developed a large and loyal fanbase who relate not only to his music but also to his journey. Since being released from prison in 2016, where he served a five-year drug-related sentence, Struggle has performed for sold-out crowds across the country and released multiple projects. He is finally poised to secure his position as the Godfather of the burgeoning Outlaw Hip Hop Rock & Roll movement.

Thank you so much for joining us in this interview series! Before we dive in, our readers would love to learn a bit about your “origin story”. Can you tell us the story of how you grew up?

Thank you for having me! I grew up in a single parent home; my mother & father split when I was 4, & my father was later killed when I was 10. My mom was 16 when she had me, so we kind of grew up together learning life as we went. She was the daughter of country music star Waylon Jennings & Jessi Colter, & was also an aspiring singer herself. She didn’t want any handouts from my grandparents, & wanted to prove she could do it on her own. When I was 11, shortly after my father was killed, we moved into low income apartments on the other side of town. Growing up I would spend the weekends at my dad’s side of the family on the west side of Nashville, & sometimes at my grandfather Waylon’s house playing with my Uncle Shooter, who is only a year older than me. I guess you could say that I kind of ‘straddled the tracks.’ I saw what was possible with the mansion, the Cadillac & Jaguar in the driveway, but going home to a neighborhood of poverty where the only ones with Cadillacs were drug dealers. I quickly gravitated toward a life of crime in and out of juvenile detention until my dad’s brother got custody of me at 16. I dropped out of high school to go to work because I missed too many days of high school selling drugs for them to pass me. I started having kids at 19, & throughout my 20’s I spent most of my time dealing drugs & in & out of jail. By the time I was 30 I had landed a long term prison sentence, leaving behind a wife and 5 kids. I immediately decided that it wasn’t the legacy I wanted to leave my kids, so while I was in prison I completely turned my life around. I got in the best shape of my life, physically, spiritually, mentally, & emotionally. I came out with a mission & purpose to inspire others that regardless of what they’ve been through, they can overcome & turn it around. By the time got home from prison my kids were in foster care & my wife was in the streets strung out on heroin. She later passed from an overdose as I fought to regain custody & rebuild a life of stability for my children. I had been making music before I went to prison & released an album while incarcerated. I came home to nothing except for a dream & the determination to prove to myself & to my children that our story was just beginning. 6 years later I have custody of all my kids, remarried with two incredible stepchildren whose father passed from an overdose. Since coming home from prison I’ve built a career & life to be proud of. I bought my children the biggest house they’ve ever stepped foot in, started a record label, got a gold record & a couple #1 Billboards, & I spend every day of my life trying to shine light on those in the dark.

Can you share a story with us about what brought you to this specific career path? I always had a love for music; I remember sitting at the foot of my mother’s piano as she sang songs that she wrote or hymnals. Regardless of what I had been through that day, the music always took me to a better place. I quickly learned that I had a gift of writing & being able to put a story & an emotion into words. I spent most of my life with one foot in music & one foot in the streets until I made the decision that music was my path, & that there were no other options.

Can you tell us the most interesting story that happened to you since you began your career?

I’ve had a lot of pinnacles from working with some amazing artists that I never thought I’d work with to producing a record with my first born daughter, to starting a record label & giving other artists a platform & opportunity to chase their dreams. To pinpoint just one story as the most interesting would be almost impossible because every day almost trumps the last.

It has been said that sometimes our mistakes can be our greatest teachers. Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Mistakes are definitely our greatest teachers. I tell people all the time that prison was the best thing that happened to me. I live with no regrets because every decision, every mistake, & every time I stumbled along my path, it led me to where I’m at right now. I’m grateful for every mistake & for every lesson that I found in the midst of it.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I have a handful of people in my life that have been writing for decades. One is my brother Jelly Roll, he has been a huge supporter of mine, & was such an inspiration while I was locked up. He was out here grinding & touring the country, letting me know that it was possible. When I came home he gave me the opportunity for us to do the Waylon and Willie albums, which changed both of our careers forever. Yelawolf has also been a great friend, & an artist I’ve learned a lot from the last 15 years. He’s another one of my biggest supporters, & might believe in me more than I believe in myself sometimes. I also have to mention my good friend Sebastian, who was the first person to ever sign me & give me a chance. He’s still by my side to this day, almost 20 years later dedicating his life & his work to building my brand. Of course my wife & kids, all the family around me, the artists on my label, & the employees that work their asses off to help this whole thing move along. And I really I couldn’t have done it without the fans. They watched me go through many phases of my life, ups & downs, & they continue to ride with me, sharing their stories of strength & hope. They say my story has inspired them, which in turn inspires me daily to not give up & let them down.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

I have a couple of quotes that I live by, one is from Bruce Lee, he said, “I don’t pray for an easy life, I pray for the strength to endure a hard one.” It always resonated because the harder my life got, the more it made me work. The harder I worked, the easier things got, which really taught me gratitude & humility. Even though life is a little easier than it was before, I still go through so many hardships. I’ve lost so many friends & family in the last few years to drug overdoses, long term prison sentences, cancer, drinking & driving, & suicide. One thing I’ve realized is that every time that happens, it gives me another story to tell & in turn inspires someone to hold on & to keep pushing if they’re going through the same thing. The hard life I’ve been dealt has touched a lot of people & helped others turn their lives around.

What are some of the most interesting or exciting projects you are working on now?

I just finished up my newest album Monte Carlo where I dove into a whole new realm by singing. I felt like I hit the peak of what I can do rapping; I’ve perfected my style, formula, & what I do as far as rapping. Diving into singing was almost like starting over in a whole new journey. It’s very raw, real, & one of my most vulnerable projects to date. I also produced an album with my right hand man ScatteredBrains & my daughter Brianna Harness called Cowgirls Don’t Cry, which is amazing to say the least. We also just finished Caitlynne Curtis’s new album All For You, where we dove into the pop world & made it our own. All the projects coming from Angels and Outlaws this year are, in my opinion, some of the best music ever created.

We are very interested in diversity in the entertainment industry. Can you share three reasons with our readers about why you think it’s important to have diversity represented in music, film, and television? How can that potentially affect our culture?

In a world full of people trying to fit in or following a bandwagon, I think it’s important to have honesty & integrity in every creation. Diving into the elements & cultures inspired me to make them my own, while paying homage to those who paved the path before me. Giving ppl something to relate to, something to hold on to, & something that makes them feel as if they are understood & not alone in their struggles has been one of the things that has meant the most to me. We all come from different places & different backgrounds, yet all of our struggles are the same in the aspect that we’re given obstacles & hardships in life that give us an opportunity to rise above them, strengthen ourselves, & overcome. Letting people know they’re not alone in their struggles & having that sense of unity & understanding for others & the things that they face is so important. I was an 80’s baby who grew up on hip-hop, & rappers like Tupac spoke to me & into the life that i was living, but also on the weekends hung out around a bunch of guys that were listening to country or southern rock ’n roll, so adding those elements into my hip-hop background only made sense to truly reflect who I was.

What are your “5 things I wish someone told me when I first started” and why? Please share a story or example for each.

I didn’t have many people in my life that had much experience in what I wanted to do. My grandfather passed before I chose music as my path completely, but I told him I was rapping & that I wanted to make music. The one thing he said that resonated was “If you just tell your story & you’re honest, you’ll realize there are millions of people going through the same thing you are.” That played such a role down the line as I embarked on this journey of music & built my brand on my story, the story of those around me, & the honesty of every mistake, every triumph, every failure, & every success.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

I see so many other artists give up or get fed up & burn out way too quickly. They either let the money make them paranoid & they quit trusting the people around them & isolate, or they pay attention too much to the numbers & they get discouraged when they don’t grow fast enough or any sign that they’re falling off. The one thing I would say to anybody is do it because you love it, do it for a purpose, find your mission statement & live by it. Once it becomes a job & once you get too caught up in it & the industry itself, it’s easy to lose sight of why you became an artist in the first place. Create the music you love, tell your story, & enjoy doing it. Whether there’s 5 or 5,000 people in the room, you gotta be grateful for the 5 that showed up to listen to your story & to hear you sing. I live by purpose over popularity, so even in moments I feel defeated because things might not be exactly where I wish they were, I have to remember that I’m still doing what I love to do & I’m still better off than where I thought I would be. Also remember that there are hundreds of thousands of people out there grinding & wishing they had a stage to stand on, so if you have that opportunity and you’ve been blessed with an audience, keep that in mind.

You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

I really just want to shed light & share my story to let people know they’re not alone, that we are all one, & regardless of color, race, religion, or creed we are all human beings. If I could strike just a lil bit of peace amongst the masses & bring a little bit unity & love, that would be a huge win in my book.

Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might just see this, especially if we tag them. :-)

I think I would love to have breakfast with Dwayne ‘The Rock’ Johnson. We went back & forth online & he’s posted my music before, but to be able to sit down & talk about life would be amazing. He himself has overcome a lot & inspired millions of people, & continues to raise the bar.

This was very meaningful, thank you so much! We wish you continued success!