Rapper Struggle Jennings Talks Famous Family Legacy, Prison & Redemption On New Album “Troubadour of Troubled Souls”

Struggle Jennings: Photo Credit - Credit: Alectra Busey

Waylon Jennings’ grandson Struggle Jennings discusses his sound, biggest influences, his family lineage, music being therapy, the response to “Waylon & Willie IV” and more!

Struggle Jennings pours his heart and soul into his music, and you hear it with each release. Hailing from Tennessee, the prolific Southside rapper is step-grandson to Waylon Jennings and grandson to Jessi Colter, inheriting the same musical genes and talents while keeping his family’s legacy alive. 

However, he’s an artist in his own right, with one hell of a story to tell.

Embracing the obstacles and life struggles he faced as a teenager to doing a 5-year stint behind bars, the rising star fully embodies his moniker: Struggle Jennings. 

Through his music, he’s able to share personal and vulnerable experiences, records that help himself as much as it helps listeners.

Describing himself as “the troubadour of troubled souls,” also the name of his forthcoming album, Struggle Jennings, real name Will Harness sees himself as a poet of the broken. Most recently, he released his new collaborative album with Jelly Roll titled Waylon & Willie IV, also releasing the official music videos for “Good Die Young” and “Comfortably Lonely.”

AllHipHop: Why are you the poet of the broken?

Struggle Jennings: I’ve been through a lot, hence my name, but I also overcame a lot. I keep my music super honest and transparent so that those going through the same thing have something that gives them hope. I want people to know they’re not alone and know that other people are out here going through it and that they can make it out of it.

AllHipHop: How would you describe your sound, if you could?

Struggle Jennings: I’m from the streets. I’m an 80’s baby, grew up in the 90’s on rap and hip-hop. Of course, I’m from the South and come from a musical background. My family was in country music – I have a family member in the Rock & Roll Hall of Fame. My uncles and everybody listened to country or Southern rock so I absorbed a lot of that. Myself… I grew up listening to Tupac, UGK, the whole beginning of rap through the late 80’s and early 90’s. My sound is a collective of everything I’ve absorbed over the years.

Sometimes it’ll be straight rap, sometimes Southern hip-hop. Other times you’ll hear East Coast elements. Sometimes you’ll get that West Coast bounce out of me. A lot of times, I’ll pull in the instruments I love like the steel guitar, fiddle, or something with a lot of emotion in it to convey the emotion of what I’m saying. My sound’s all over the place. People ask “well, which ‘genre’ are you?” What is that, French? [laughs] I don’t even know what that word means anymore.

AllHipHop: Being from Tennessee, how does that play into your life and your career? 

Struggle Jennings: Nashville is Music City. Everywhere you go in Nashville, on every street there’s 5 different bars with live musicians playing. I grew up listening to a lot of 8Ball & MJG and Three 6 Mafia. Being from Tennessee makes it harder to come out of Nashville as a rap artist because of the stigma of country music, the capital’s Music City. Coming from Nashville and everything I’ve endured gave me a hell of a story to tell WITH all the different people I’ve seen. From the struggling artists to the artists that made it – it has definitely given me a sense of inspiration. 

AllHipHop: What does it mean to be step-grandson to Waylon Jennings, and grandson to Jessi Colter?

Struggle Jennings: It’s crazy because of course, it’s a double-edged sword. My mom had me when she’s 16 years old. She sang backup for my grandfather for a couple of years. She wanted to pursue her music, but she wanted to do it on her own. She didn’t want any handouts. She liked bad boys so with all the guys she dated, we ended up breaking away from the family. I still spent time with my grandfather more than any of the other grandkids, and my uncle Shooter, who is a year older than me. He’s my uncle, but more like a brother. It was a lot of pressure coming out, people think you’re supposed to fill those shoes or go in one direction.

When I first started rapping, people said “you’re Waylon Jennings’ grandson? He’d roll over in his grave.” Nah, if Waylon was alive right now, he’d be rapping too — if he was my age and raised up in the era that I was. My mom wanted to do it on her own so we ended up living in lower income housing. She worked 2 jobs and worked on her music — a single mom trying to raise me. 

With us living in that environment then me going to Waylon’s house on the weekend to hang out with Shooter or to see my grandfather and grandmother, it was completely opposite sides of the tracks. I straddled those tracks: “okay, well this is possible because Waylon came from dirt floors in Texas. Now he’s got this big house, Cadillacs, Jaguars, Mercedes, maids…” Then back to being in my mom’s one-bedroom apartment where she took the living room so I could have a bedroom-type environment, it gave me a sense that it’s possible. What really drove me through a lot of the dark places I went and pulled me out of the mud was having that sense of “this s### is possible.”

AllHipHop: New album Waylon & Willie IV in collaboration with Jelly Roll. How does it feel for it to debut at #2 in the iTunes Hip Hop Albums chart? 

Struggle Jennings: It was beautiful. Me and Jelly Roll have been friends going on 20 years now. From my past life, we were both in the streets together. He did time. I did 5 years in prison, he held me down the whole time I was down. With me coming home and transitioning, he’d already built a base and a platform. 

Going through that same inspiration and hope like “oh okay, we can really do this.” Waylon & Willie I did incredible. Waylon & Willie II took off like nuts, we toured it. We dropped Waylon & Willie III, then this one was super special. We’re both at different points in our career now so to be able to get back together and throw all the b####### out the window, 2 friends go in there like it’s 2002 again and cut records, it’s always a blessing.

AllHipHop: “Enemy” is at 1.5 million views on YouTube in a few months, how does that make you feel?

Struggle Jennings: It’s doing pretty good. We’ve had some big ones like “Fall In The Fall,” it’s over 58 million now. When me and him get together, it’s magic. “Enemy” was especially good to see people rocked with it because it’s such a meaningful song. 

Jelly and I lost one of our best friends last year to a home invasion so the song had a lot of meaning. We used old footage for the video along with his studio performance. To be able to watch it back and relive those moments was surreal, some of that footage you see in the “Enemy” video is from ’08. Anytime the supporters or the fans really cling onto something, share it and show it love is always nice. We’re telling our story and our life, it’s really personal when you do that and people f### with it.

AllHipHop: What inspired “Good Die Young”?

Struggle Jennings: The same thing that inspires all of them. I’ve got 7 kids and I came home 4.5 years ago. At that time, my kids were in foster care. I had an ankle bracelet on in a federal halfway house, and I went and lived in my brother’s basement.

I had just closed on our new house that I bought for my kids. I’ve got custody of all my kids now. It was one of those nights. A bottle of tequila and a whole bunch of reflecting, really thinking about how I want my kids to remember me. 

The song’s saying I know I’ve been a bad guy, but I’ve always had a good heart. “I played the part of the villain, but I’ve been a hero for my children. When I’m no longer living just remember all the good parts.” Really speaking on this is who I am, I’ve always done my best to be my best even at my worst. I hope that’s what they remember me for. 

AllHipHop: How’s fatherhood? I know family’s huge for you.

Struggle Jennings: With me, it’s family over everything until everything is gone. They’re my world, my life. They’re my inspiration, the reason I get up every day and keep pushing. Going through everything we’ve been through as a family, my 3 youngest kids lost their mother to a drug overdose. 

My 2 stepkids…we buried their father a month and a half ago to a drug overdose. I’ve lost a handful of friends. My wife…. she’s been my best friend for 15 years. We were in separate relationships so now we’re the two that made it out of the storm. We are protecting the babies…giving them the best life they’ve ever lived. They taught me everything about life, about love. My kids are the best. As much as I am they’re foundation, they’re my backbone. 

AllHipHop: How is music a coping mechanism for you? Just with everything you’ve been through.

Struggle Jennings: Music’s definitely therapy, since day one. I started off writing poems when I was a kid, then writing raps. I gave it up and went back to the streets. Did some time, started writing while I was in jail. The first time I did 2 years back in 2000, writing the whole time. When I got out, I was a single dad. The first bit of money I saved up, I bought a studio. Before that, I was recording in my closet. I’m a guy that really lives off faith and hard work, I believe those are the keys to success. Having music as such a passion and a driving force for me always gave me something to work for…something to have faith in. Even when everybody around me is dying or getting busted, it always gives me something to hold on to.

Of course, the therapeutic aspect of being able to put all that out on wax and record these songs. Now, one of the biggest things that keeps me sane is getting on Instagram or YouTube and watching all the comments. People pouring their hearts out saying “your music helped get me off the drugs” or “helped me through some addiction or prison sentence.” “My mom just died and your song ‘Your Little Man’ has gotten me through this.” Now I can’t go back because I can’t let them down. They’re looking at me like I made it through it, they can make it through it. Between music, the gym, and my kids, that’s the only thing that keeps me from going off the deep end. 

AllHipHop: Biggest lesson you learned behind bars?

Struggle Jennings: The biggest part of my transition in prison was definitely letting go of all the irrational beliefs. As a kid I was taught: you feed your fam by any means necessary. It’s okay to do wrong as long as you’re doing it for the right reasons. Those old street codes were instilled in me as a child by my father and uncles. I’d always been the guy that felt I had control of my family, control of my environment, control of my money. Going into prison and not having control of anything outside of that cell: watching my baby mama get strung out on drugs, watching my kids be tossed around traphouses and going into foster care, watching my world and everything I held dear crumble and be affected by the decisions I made.

The fact I wasn’t there for them anymore gave me a whole new perspective on life: what mattered, what was important, and who I was as a person. I had to strip all the way down. I had to completely work all the way down to my childhood and say “okay, what is it that keeps sending me back to prison? Why do I keep making these decisions?” Because I feel I’m doing it for the right reasons, or at least I’m justifying it. I’m blaming my decisions on my conditions, instead of changing my conditions. The book that I’ve been reading that has helped me a lot is The Four Agreements.

AllHipHop: Yeah, everyone’s been talking about that recently!

Struggle Jennings: I’ve been talking about it for 10 years. I’ve been preaching the gospel of it. A lot of my mistakes and bad decisions in life were based on taking s### personally…allowing somebody else’s perception to rest on me and feel like I had to prove them wrong, getting violent or whatever it may have been. When in reality, how somebody sees me isn’t a reflection of me. It’s a reflection of how they feel. I love that book, definitely one of the biggest tools I used from it.

AllHipHop: What can we expect from your forthcoming album, Troubadour of Troubled Souls, out this Friday?

Struggle Jennings: It’s a complete reflection of me, who I am. There’s so much – this album’s special. I ended up having to break it up into 2 albums. The next one will come out in fall, but I locked in this year. 2020 was crazy. With us not being able to tour, the temperature, everything going on in the world, I had a lot of time to reflect. I started a record label, signed 5 artists and spent all of 2020 locked in the studio. 

Troubadour of Troubled Souls was a collection of all the different stuff I went through. Not only me, but watching others I love going through it. Thinking about what my family went through, peers, the world in general. To date, it’s one of my favorite projects ever for sure. I’m excited! I want to talk more, but I don’t want to gas it up. I want them to hear it because I’m really excited for this album.

AllHipHop: What does it mean to have features with Yelawolf, your daughter Brianna, Jesse Whitley? I know Yelawolf is a longtime friend for you.

Struggle Jennings: Yelawolf’s my little brother man, he’s little big bro. He’s actually older than me. [laughs] Anytime I get in the studio with him, it’s amazing. He’s a musical genius and a good friend, we have fun in here. Everything with Brianna, those are some of the most proudest moments of my life watching her blossom into the artist she’s becoming. Got Caitlynne Curtis on “God We Need You Now” and “Soul on Fire,” one of the artists I signed this year. She’s amazing.

Jessie Whitley’s a longtime friend. He’s the son of Keith Whitley and Lorrie Morgan: country music royalty. He lost his dad at a young age. He lives a couple blocks from me, we have so much in common. Getting in and locking in with him, I love writing with other people. I love bringing people in and saying: “man I went through this, have you ever been through this?” 

Struggle Jennings: We find some common ground, we go back and forth with the emotions that we felt and really dive into whatever it is we’re talking about. I got a chance to do that with Jesse Whitley, that was amazing. I’ve got JD Huggins on the album on a song called “Man Like Me,” that’s super rowdy. He’s a rock singer I just signed to my label as well, I got the fam all on there.

AllHipHop: What’re you most excited for with the tour kicking off with Brianna and Caitlynne Curtis on May 1st?

Struggle Jennings: I’m excited to get back out on the road. 2019, I did 191 shows. 2020 we started off the first month with 20 shows on the West Coast, then COVID hit. This is the first time I’ve been able to get my guys really back out on the road: go out there, hug people and shake hands. See fans and give that back out. I’m super excited for the fans to see Brianna and Caitlynee. I’m ready to get out there, see some beautiful scenery. Meet some beautiful people, rock them stages and drink too much tequila.