Struggle Jennings lives up to the name. The grandson of Jessi Colter and Duane Eddy, raised in part by Waylon Jennings, the rap-cum-country maverick came of age on West Nashville’s mean streets. His father was murdered when he 10, his mother struggled, and he got into dealing and rapping to make his way.

A year younger than his uncle Shooter Jennings, he balanced a rough home life in the hood with trips to his legendary grandparents’ home—and made a name as a rapper before pulling straight-up country into his mix. With 2023’s Monte Carlo and April’s El Camino (via ONErpm) being aggressive outlaw-meets-rap, the music is full-throttle, raw and real. But having survived five years in prison and losing the mother of his seven kids to an OD, he’s leaning hard into being smart about how you love.

You were in Kentucky, talking to elected officials about the opioid crisis.

One of my kids overdosed and died. The father to my stepkids overdosed and died. My kids’ grandmother, my kids’ grandfather, a couple of my kids’ uncle—that whole family is wiped out from drug abuse and overdosing. I have 100 friends probably, in the last several years who have passed from drug overdoses. Being blessed to have been given a second, third, fourth chance, with everything that I know, and making it through all the things I went through in life, I feel that responsibility. It gives me a purpose.

I used to say “purpose over popularity.” I’m not going to make music that reflects a behavior I don’t want my kids or myself doing. I’m not going to. If I can sell 100,000 records and change 100 lives, that is so much better than selling 10 million and ruining one.

That’s straight up.

I’ve realized being a man and a father, a lot of men put a tough-guy facade on, don’t cry, but it’s not real. We should be able to show emotion, be honest, be exactly how we feel. Talk baby talk to a baby and die protecting them in the same breath.

Me taking a stand, saying, “That shit ain’t right,” “No, leave the kids alone,” “Get off drugs, go to work, stand up, dust yourself off, stop blaming” is important. I understand anxiety, I understand depression. There came a point where these young men started leaning on it and using it as a crutch. I get anxiety all the time; take a deep, deep breath and say, “Hey, this is just anxiety. I can get through this. I got stuff to do.”

You’ve lived it.

For so long, being the tough guy and trying to carry this façade kept me in prison, because I wanted to be a baller; I wanted to be a bad guy, a gangster. In the end, I realized being a gangster is taking care of your family, the ones you love, being a strong leader, someone people can look up to.

For a long time, I made dope-boy music, and it was real. I was really living that life—it sent me straight to prison. I justified that I was doing it for my fans and my kids. In the end, they were the ones who were the most impacted.

My kids got dragged to drug houses after I left, ended up in foster care, went through hell while I was in prison. I came home, fought for them—I got them back. All my kids are doing great, you’d never know they went through that unless you had a conversation with them. Then you see the strength and resilience, that they’ve been through some shit.

Who was your role model?

Waylon was a role model, because he was my grandfather. I got to see the duality. I got to see him being a family man—because I was in the house with him—being a father, a grandfather and a boss. But I always knew that outlaw side from the music, from being a kid at school and people saying, “Your grandpa’s not a country star, he’s just a drug addict.”

I always grew toward the outlaw side, because that was cool. Billy the Kid was more loved than Hank Aaron. There’s always been a beauty to being an outlaw. I wanted to be Tony Montana when I was a kid. I thought I was going to be a big drug lord. I listened to music that pumped that into me from a young age. …

I had a really big drug case, and I made a lot of money selling drugs. I didn’t get to keep any of it. Was it worth it? Absolutely not. Would I take it back? No. Because it gave me a story, a testimony, it gave me something I can show other people, to say, “Hey, regardless what you’re going through, this is what I went through—and I made it on the other side. You can, too.”

You brought country to hop hop.

I was the first to put steel guitar on a rap record—I sampled Waylon on “Outlaw Shit” in 2008. I was the first really mixing country with rap. Yelawolf was the first I ever heard putting fiddle and those crazy fucking arrangements. I was just poppin’ out mix tapes.

When I first recorded “Outlaw Shit,” Yelawolf was the only one who saw it and jumped on that song with me. I didn’t put that out till 2010 because everyone was telling me, “Aw man, you can’t mix country and rap, it’s going to be career suicide. You need another club banger,” so I left that record sitting there. I went and did a bunch of records with Drumma Boy; I was trying to be the white Rick Ross.

I was really in the middle of the streets—really selling cocaine, really carrying a gun and running with a gang. When that all came crashing down, I’d recorded I Am Struggle before I went to prison, which is the album I sampled Waylon. “Outlaw Shit” was 2008, so me and Yelawolf were on the cutting edge of that.

So far beyond Music Row, so from-the-streets. Clearly it wasn’t chasing hits.

We weren’t in for a hit record, we were doing what felt good to us and true to our roots. We all grew up listening to rap, but we’re ’80s kids—our uncles and dads were listening to Waylon, Lynyrd Skynyrd, ’90s country. We grew up with country being a backdrop, the soundtrack was rap.

At first we were just rapping beats. As soon as we learned how to implement music, we started implementing all those pieces. It was always my dream to do country music. Jelly Roll said to me the other day, “Struggle, you told me 20 years ago that you were going to have gold teeth singing country music.” He said, “I thought you were crazy.”

Now look.

They messed up and let Jelly in the door. He snuck around and let his friends in the side. We’re in here now, and we’re changing it internally. I love what’s happening in the genre and subgenre of country and country rap. Just so many, me and Jelly, a handful of others. Brantley Gilbert is one of us. I’m so excited to tour with him next month.

Ryan Upchurch, Cheatham County, born and raised. Started as a comedian on Vine, got a huge following. Started rapping about country stuff because he’s a real country boy. Started doing music, did a couple rock albums, country albums. Probably one of the most successful independent artists in the game, period.

Your voice has changed.

Back as far as Monte Carlo, then my new album, out in April, El Camino, the mixing engineer would send tracks back, I’d be, “Absolutely not! You may have cleaned it up, but you took out all the shit that was cool. I only have a couple things that are cool. You smoothed it out. Put that (gravel) back, I don’t want any autotune at all. Take the emotion out? Absolutely not!” I want you to feel it.

That’s why Waylon loved you so much. He really did. We talked about you.

I remember that ’90s era. Waylon’d be like, “What do you listen to?” I’d say, “Bell Biv DeVoe. I like rap.” He’d say, “Let me hear it.” I’d start rapping for him in the living room. Ever since I was 8, he called me “his only Black grandson,” because I had that swag, that demeanor.

We had the most amazing relationship. I get so mad when these interviewers or blogs—because they’re doing their due diligence, but they’re “stepgrandson of Waylon.” I’m like “That was my pawpaw.”

Then you have the hater fan: “He’s using his grandpa’s name, and he’s not even really related.” I’m like, “That was my father.” My dad was murdered when I was 10, so Waylon was my dad. I’ve stood on my own, haven’t tried to use his name, haven’t tried to sound like him. I made my own life, I made my own struggles, I made my own name, I went through my own pain. But yes, I represent the last name, and I wear the flying W a lot. I cry for who my grandfather was and the legacy he left, the man he was.

I’ve got an offer to sell my catalog, where it could be really life-changing money. I was talking to Shooter, who said, “Bro, they’re going to give you 15 times what it made this year. You know your grandma’s bills are still being paid off work Waylon did 50 years ago.” And that’s fine. … I want my grandkids and my great grandkids to still be eating off of what I did when I’m long and gone.