MORGAN: Struggle Jennings On Getting Shot, Surviving Prison, and Carrying a Legendary Name

Summary

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Podcast Summary: The Bobby Bones Show

Episode: MORGAN: Struggle Jennings On Getting Shot, Surviving Prison, and Carrying a Legendary Name
Host: Morgan (Premiere Networks)
Guest: Struggle Jennings
Date: September 1, 2025

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Main Theme / Overview

In this riveting episode, Morgan sits down with rapper, country artist, and legendary namesake Struggle Jennings. Together, they explore Struggle’s tumultuous yet inspiring life journey—from a chaotic and traumatic childhood through the dark chapters of gang involvement, addiction, being shot, and multiple stints in prison, to becoming a devoted father, community leader, and thriving independent musician. The conversation is raw, emotionally charged, and full of candid reflection, centering around themes of resilience, redemption, legacy, and the transformative power of taking ownership of one's story.

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Key Discussion Points and Insights

1. Growing Up Jennings: Dual Realities and Early Struggles

• Struggle shares stories of “always being the new kid,” moving often with his young single mother (03:44), learning early how to make friends by bringing snacks.
• Explains his stage name: Given “Struggle” by a friend upon returning from jail, moving on from his less “digestible” street name, “Lil Killer”. “You gotta go by Struggle… I ain’t seen nobody go through the stuff you go through on a daily basis” (05:04).
• Discusses his extraordinary family tree—grandson of Waylon Jennings and Jessi Colter, son of a teenage mom, raised amidst both poverty and the wealth/fame of Nashville music royalty (07:19).
• Endured family trauma: An abusive stepfather, his dad’s murder (originally told as a suicide), and his mom’s deeply independent struggle to provide.

2. Sliding Into Crime, Addiction, and Survival

• Struggle openly explains being drawn into dealing and gang life from a young age, influenced by both street role models and proximity to privilege (11:26).
• Laments, “The only people that had the Cadillacs and Jaguars were the drug dealers. So I always gravitated toward that” (11:30).
• Admits there were times music was sidelined: “There was a time where I wanted to be Tony Montana… Tony Soprano, John Gotti… went through different periods, eras of struggle.” (14:03)

3. Near-Death Experiences and Prison

• Struggle recounts being shot twice: “I got into a shootout there [at Big Bad Breakfast], got hit in the shin. It actually ricocheted under the car and hit me” (19:43).
• Details a destructive cycle: periodic stints in jail, attempts at turning life around, relapse into crime—“I knew I was good at being bad” (20:59).

4. Fatherhood, Grief, and Hitting Rock Bottom

• Shares deeply personal accounts of the consequences his choices had on his children: While in prison, his ex-wife spiraled into addiction, his daughter had to make dinner for siblings, and eventually his children entered foster care and faced trauma (24:00).
• Moving story of accountability: “I had to really take full accountability for all of it… I left my wife out there without a husband, my mom without a son, my friends without their friend…” (25:12).
• Daughter Innocence, after surviving immense hardship, graduated with a 3.9 GPA—his proudest on-stage moment (25:01).

5. Rehabilitation, Transformation, and Choosing a New Path

• While incarcerated, Struggle immerses himself in self-betterment: “Parenting, finances, critical thinking, anti-violence programs… just trying to learn how to reel your anger in” (28:43).
• Highlights importance of active change: “Change happens when the reality of the outcome becomes scarier than the fear of change” (27:00).
• On returning, completely different: “I lost 120 pounds, rid myself of a lot of irrational thinking…” (26:45).

6. Vulnerability, Grieving, and Being a Dad

• Shares learning healthy grief: “I had to put my grieving on the back burner… I’ve learned that’s not always healthy… Gotta find your own time to grieve” (33:27).
• Reversal of toxic masculinity: “The older I get, the more I realize real men cry… We have emotions… You gotta allow yourself to feel those emotions.” (35:28)
• Talks about raising five children and two stepchildren, especially as a “girl dad”, imbuing resilience in each (39:06).

7. Legacy, Music, and Standing in His Own Light

• Explains pressure and pride of being “Jennings”: “I could never be Waylon Jennings, but I can do the hell out of Struggle Jennings.” (45:12)
• Waylon’s advice: “Don’t try to stand in my light… find your own light. Be yourself.” (46:18)

8. Staying Independent, Staying Real

• Shares candid industry insights: prefers indie path, releasing prodigious amounts of music: “13 or 14 albums out, 85 unreleased songs” (55:44).
• Collaborative projects, working with Brian Martin, Shooter Jennings, Brantley Gilbert, and venturing fully into both rap and country.
• On independent hustle: “I just like to still be able to go into Kroger and shop. My community loves me…” (59:48).

9. Community, Service, and the Message of Redemption

• Struggle is now the Director of Send Musicians to Prison—sharing music and testimony in jails nationwide.
• Central message: “Don’t let your past define you… Anything you’ve been through is leading you up to where you’re supposed to be. Don’t be afraid of those flames.” (61:00)

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Notable Quotes & Memorable Moments

• On his stage name’s origin:
  “I don’t know if a parent's gonna let her kid buy a CD from ‘Lil Killer’ ... My friend said, ‘You oughta go by Struggle. I ain’t seen nobody go through what you go through.’”
  – Struggle Jennings (04:32)

• On living between two worlds:
  “When I was in West Nashville, I learned a lot of those irrational beliefs… that outlaw mentality… then I’d go to Whalen’s and see the Jag, the Cadillac, the maid, and the nanny.”
  – Struggle (11:26)

• On redemption:
  “I have no regrets in life… everything I went through brought me to exactly where I’m at, made me who I am.”
  – Struggle (12:11)

• On coping with pain:
  “Try to be too tough, you’ll find out how weak you really are.”
  – Struggle (35:28)

• On the impact of prison:
  “I had to really take accountability for all of it... I left them out there without a father…”
  – Struggle (25:12)

• On legacy:
  “Don’t try to stand in my light… find your own light… you may not be everybody’s cup of tea, but you’ll be somebody’s cup of coffee.”
  – Waylon Jennings (as recalled by Struggle, 46:18)

• On motivating others:
  “I wasn’t born ready. I had to go through all the shit I went through to get ready. When they purify gold, they put it in fire... Don’t be afraid of those flames.”
  – Struggle (61:00)

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Timestamps for Major Segments

• [03:36] – Childhood, moving constantly, “learned how to make friends, bring snacks”
• [04:10] – The origin of the stage name “Struggle”
• [08:31] – Family trauma, father’s murder
• [11:26] – Growing up between “the two worlds”
• [13:13] – First drug dealing, getting into crime as a teen
• [15:50] – Being shot, living dangerously
• [24:00] – Impact of prison on family, daughter’s story
• [26:45] – Prison self-work, drug programs, transformation
• [33:27] – Grieving process, handling loss
• [39:06] – Fatherhood, raising daughters and sons
• [45:10] – Musical legacy, Waylon’s advice
• [55:44] – Releasing music, upcoming records, working with peers
• [61:00] – Redemption message, summary advice: “Don’t let your past define you”

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Conclusion

This episode offers a powerful portrait of Struggle Jennings’ life: an unflinching reckoning with pain, loss, and the hazardous allure of outlaw living, transformed by accountability, tenderness, and an ever-present creative drive. The conversation will move anyone interested in stories of redemption, family legacy, and the complex realities behind musical success.

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Recommended for:
Listeners who seek stories of overcoming adversity, music fans, those affected by addiction or incarceration, and anyone inspired by real-life redemption arcs.

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Transcript

[Morgan]

This is an iHeart podcast.

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[Announcer]

Take this personally with Morgan.

[Morgan]

The incredible stories are continuing. I can't wait for you guys to listen to this interview. You may have heard of this guy in a whole bunch of different ways. Maybe you listen to one of his rap albums or maybe his country albums or you followed along with him on social media. Or maybe from his famous grandfather. His name is Struggle Jennings. He has a story full of resilience and he's being open and vulnerable about so many things that have happened in his life. It's one of my favorite interviews to date. So without further ado, let's get into it. Morgan here I'm joined by Struggle Jennings, and I'm really excited because Struggle and I met, gosh, three or so years ago. We played in the Folds of Honor celebrity softball game. So, Struggle, thanks for joining me. This is awesome.

[Struggle Jennings]

No, thanks for having me. I got to carry that trophy home that day.

[Morgan]

You did?

[Struggle Jennings]

I was supposed to give it to Jelly, and he never picked it up. So it is on my mantle.

[Morgan]

I love that you're like, by the way, it's just mine now. My first introduction to you was you pulled out a whole bunch of snacks out of a backpack, and I was like, I like this guy. Yeah, the dude.

[Struggle Jennings]

I knew it was gonna be hot, and it was gonna. I was gonna have a lot of friends and just bring snacks.

[Morgan]

You knew how to make friends. Like, you knew the momentum there.

[Struggle Jennings]

I grew up in a household where my mom. We moved, like, every nine months or something. Six to nine months or every year. My mom was 16 when she had me, so. So she was one of those kind of, I need a fresh start. And we'd move to the other side of town or we'd move here. And so, yeah, I learned how to make friends. When you're the new guy, bring snacks.

[Morgan]

And talk to me about your life and your childhood, which also, one of my, like, questions, Is Struggle your real name or is this just a stage name?

[Struggle Jennings]

Stage name.

[Morgan]

Okay. And why. What is Struggle? Like, where did that come from?

[Struggle Jennings]

So I was actually with a friend of mine, and I started rapping. I just came home from a jail sentence, and I was a single dad with my two kids and really trying to get my rap career off the ground. And. And of course, I had a name in the streets.

[Morgan]

Okay.

[Struggle Jennings]

But I was like, I don't know if this name is really digestible. I don't know if a parent's gonna let her kid buy a CD from little Killer.

[Morgan]

That was your name in the Streets.

[Struggle Jennings]

When I was a teenager.

[Morgan]

Do you get that name, or does somebody give you that name?

[Struggle Jennings]

Somebody gives it to you.

[Morgan]

Okay.

[Struggle Jennings]

And the same way with Struggle is a friend of mine. We were working. We were about to go do our first studio session, and we had been, like, practicing and writing songs, and me and him were doing, like, an EP together, and a guy named White Boy. And he was like, man. He was like, what are you gonna go by? I was like, man, I don't know. I just. I guess it'll come to me. And he was like, man, you ought to go, I struggle. And I was like, struggle. And he was like, yeah, bro. Like, I ain't see nobody go through the stuff you go through on a daily basis. He was like, you need to by struggle. And I was like, all right, cool. So I started going by. At first, it was like, young struggle.

[Morgan]

Yeah.

[Struggle Jennings]

And as I got older, it became struggle. And then my grandfather being Whelen, when I caught my case, they automatically started calling me Struggle Jennings. They're like the grandson of Waylon Jennings, rapper Struggle Jennings. And I was fighting it at first. I was like, man, I was telling my guy that was handling my socials, and that was before Instagram or anything like that. My Twitter is still young strugg at young struck. He was like, nah, man. He was like, dude, if you Google struggle, it's gonna pop up like kids in Africa and all kinds of. All kinds of struggles that are, like, going on. He was like, struggle Jennings, it'll be Google. I was like, man, I don't know. And I. So I called Michael Shooter, and he was like, nah, Waylon would love that. He was like, take that name and make it your own. And so I rolled with it. When I. By the time I came home, there was really no reversing it.

[Morgan]

It had already been done. Like, you already became Struggle Jennings. And you just mentioned your mom and talk to me about childhood because you talked about your friend saying you went through a lot of struggle.

[Struggle Jennings]

Yeah.

[Morgan]

What were some of those moments in your life that led to where you are now?

[Struggle Jennings]

Yeah. So, I mean, starting early. My mom was 16 when she had me, and she's the daughter of Jesse Coulter and Dwayne Eddie, who's legendary guitar player rock and roll. And Jesse and Waylon had ran off together when my mom was like four and moved from California to Nashville, and Waylon adopted her and so forth. And then she had me at 16. She met my dad. My dad was an old West Nashville. Came from poverty, just rough neck, good old boy. And they met at the West Nashville skating rink. And one starry night in the back of his El Camino, I was made.

[Morgan]

You love to tell that story, don't you?

[Struggle Jennings]

I can tell, yeah. I love that I'm about as West Nashville as they get. So they lasted till I was about 4. My grandpa bought them a house in Franklin and a neighborhood called Maplewood. There was only like four or five houses when he bought the house, and it was like just single story, cute little house in Franklin. And then the neighborhood built up. By the time I was six. There was probably 250 houses in the neighborhood. Yeah, but it was a pretty enclosed neighborhood, like, one way in, one way out. So as a child, I had a pretty normal upbringing. Like, pretty clean cut. My mom was 16. She was. She was. We were raising each other. The firefighters were at our house every day because she was burning something, trying to learn how to cook. And I heard my dad. They split up when I was 4, so she was doing it on her own. But she was still singing back up for Whelan. So she was gone a lot on tour. And then in the summertimes, I'd get to go on the bus or. And I was at Waylon's house a lot because me and Shooter are just a year apart.

[Morgan]

Which Shooter is your uncle, though?

[Struggle Jennings]

Yeah, that's Whelan and Jesse's only kid together.

[Morgan]

Yeah.

[Struggle Jennings]

And so then when I was. Went through some stuff, like when I was, like, eight, my mom got in a real abusive relationship. She got married to another guy, and I watched him beat the. Out of her. And of course, my dad came over there and ran him off. And. But then When I was 10, my dad was murdered.

[Morgan]

I remember when we were talking before this, you had mentioned that. And were you living with your dad at the time?

[Struggle Jennings]

I was living with my mom.

[Morgan]

Okay.

[Struggle Jennings]

And so when that happened, I was outside playing football, and my mom called me and was like, hey, your dad's on the phone. He wants to talk to you. And I was like, I'll tell him. I called him back later. And then when I came in that night, she was crying in the back room. All of a sudden, Waylon and all my family pulled up and sat me down and said, your dad's no longer with us. They told me it was suicide. So throughout my childhood, I was, like, living with that regret. What if I would have answered the phone? Would he still be here? And it wasn't until I was 18 that I found out he was murdered.

[Morgan]

Were they telling you that to protect you?

[Struggle Jennings]

I assume so. My dad's side of the family knew what really happened, but they were protecting the family. And so my mom genuinely didn't. She thought that he had committed suicide. And it wasn't until I was 18 that I was, like, suicidal. And I was. I'd been living with my uncle because I got started getting in a lot of trouble. 12. I joined a gang, started selling drugs. My mom had her. And Waylon had kind of fell out because she was, like, starting to date again. And he was like, hey, son just lost his dad. You just got out of a terrible marriage. Thank you. Should chill a little bit. And she's 20 something year old young lady looking for love and on her own and alone.

[Morgan]

And she's gone through a lot of stuff at this point.

[Struggle Jennings]

Yeah, for sure. And so she was kind of had that mentality, you know what? I don't want your money. I don't need your help. I'm gonna do it on my own, and I'm gonna show you that I can do it on my own. So it was like a culture shock. At the same time, I lost my dad, we moved to the other side of town and she got two jobs and was going to cosmetology school and working her ass off trying to raise me and not cut the cord from the family, which I still was at his house a lot because I was over there hanging out with Shooter and all the holidays and stuff. But financially she wouldn't take anything from him and she was trying to prove. So we went through from what seemed like a pretty normal childhood. I'd be West Nashville on the weekends a lot to see my dad or my uncle and my cousins and stuff. So I always straddled those tracks where when I was in West Nashville, you know, I learned a lot of those irrational beliefs and just the things that kind of sparked that mentality, that outlaw mentality. But then I'd go to Whalen's house and see the Jag and the Cadillac and the maid and the nanny and.

[Morgan]

The guards and these very two polarized lives.

[Struggle Jennings]

Yeah. And knowing Whalen came from nothing gave me that sense of anything's possible. But then when I'd leave his house and go back to my neighborhood, the only people that had the Cadillacs and the Jaguars were the drug dealers. So I always gravitated towards that because I saw a quality of life that I knew was obtainable. I was just in. I allowed my circumstance to keep me. This is all I have. This is all I can do. This is all I can get. And that kind of led me into being a drug dealer most of my life. And in a life of crime, that's really tough too.

[Morgan]

Do you look back at that time in your life? Do you. Are you not necessarily happy that it happened, but do you feel like it made you who you are today to be the person that you are?

[Struggle Jennings]

Oh, a thousand percent. Like, I have no regrets in life. I mean, there's some. There's some things I wish I may not have said or a couple things I wish I hadn't done in my life. But as far as looking back or having any kind of like victim mentality, there's not like I went through everything that I went through. It brought me exactly where I'm at, made me who I am and gave me the testimony to be able to reach other people. It gave me the insight and through the different phases, I just. It kept leveling me up to the place that I'm at now as a man.

[Morgan]

Oh, and I want to ask you, because I. I grew up in rural Kansas. There's not a lot happening over there. We got a lot of farmers in country land.

[Struggle Jennings]

That's about it. Most people get in trouble. Boring is when you find to do.

[Morgan]

I did drink very early. That's very true. But there wasn't a lot of activity. I wasn't around a whole bunch. So when you get into drug dealing and stuff, I have to imagine as a kid that was terrifying. And you were doing and experiencing things that as a kid you never should have had to.

[Struggle Jennings]

For sure. I think that we were so caught up in the lyrics of Tupac and no Limit, Master P, and we just accepted that as life and that's what it was and that's what we gravitated towards. And I don't ever really remember any time in my life really being like, poor me or I think because a lot of times, because I had seen the two sides so much and I knew that Waylon grew up with nothing. They were dirt poor in Texas, dirt floors. And he made it out of there on a dream. And my dream was just shifted a lot of times. Even though I always had music in my heart and I wanted to do music, there was a time where I wanted to be Tony Montana. There's a time where I want to be Tony Soprano, I want to be John Gotti.

[Morgan]

You really went through different periods.

[Struggle Jennings]

I did, I did.

[Morgan]

And like eras of struggle.

[Struggle Jennings]

Yeah, for sure. No, there's. You can go back and look at pictures. There's times where I had braids to my ass and right where my pants were and gold chain. And there's times where I was in a three piece suit thinking I was about to start a mafia family.

[Morgan]

Do you feel like that was because you were going back and forth like you would go and hang out with your grandfather in this kind of fame filled and very successful life and you're seeing these things and you want to be this one person and then you'd go back and you'd be with your mom and you'd see this other side and you're like, Well, I kind of want both.

[Struggle Jennings]

Yeah, I still struggle with that. Right. Even there's times where my career starts lifting to a certain place and things get crazy and I'm like, man, I really just want to be home with the kids. Do I really want to be a huge country star, rapper or entertainer? Do I want to be a PTA dad and coach my son's football? There's still always that internal battle. The music just won't let me go anywhere else. I. I'm so embedded with just a love. For me, music is my life to a point. My children are my life and my family, of course. But there's. I just had that gravitational pool that I've never been able to run from it. Even when I've tried. It's kind of like, God, many a times I tried to run completely in the opposite direction and something would happen that would be life altering and a bullet would miss me by inches or whatever the case was that it could have been really a lot worse than it was and always reeled me back in to like. No, I know this is what is true. And this is true to me and.

[Morgan]

Are you telling me that you've been shot before?

[Struggle Jennings]

Oh, yeah, I've been shot twice. I actually got shot. You know where Big Bad Breakfast is?

[Morgan]

Yeah.

[Struggle Jennings]

Okay, so that used to be Wendell Smith's. It was a corner store.

[Morgan]

Okay. Wendell Smith is still there.

[Struggle Jennings]

The restaurant. Oh, the liquor store.

[Morgan]

Okay. Okay.

[Struggle Jennings]

So Big Bad Breakfast was the convenience store. So old man Wendell had the convenience store, the liquor store and the restaurant.

[Morgan]

Okay.

[Struggle Jennings]

Whole family worked in the restaurant. My aunt was a waitress there, I think my dad bus tables there when he was young. My grandma worked there. But then a guy named Jakey Cook married Wendell Smith's daughter, Beverly Smith. And so my whole life Jakey Cook was running that. And he was like a old school gambler, like okay, Southern mafia type guy. His son Benji still runs and then the grandson also runs the restaurant.

[Morgan]

Okay.

[Struggle Jennings]

But Jakey was just like cool old multi, multi millionaire that you wouldn't even, you wouldn't even know it was under the radar. Yeah, he's just cool, chill guy. A lot of them got their start with like poker machines in the back of. Yeah.

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[Struggle Jennings]

You can make a difference in someone's.

[Announcer]

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[Morgan]

These jobs offer flexible schedules, healthcare, retirement.

[Announcer]

Options and free training.

[Amy Brown]

They also provide paid time off and opportunities for overtime. Visit oregonhomecarejobs.com to learn more and apply.

[Struggle Jennings]

That's oregonhomecarejobs.com foreign.

[Amy Brown]

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[Morgan]

Wait, and so you got shot where that is now?

[Struggle Jennings]

Yeah, I got into a shoot out there when I was young.

[Morgan]

How old were you hit in the.

[Struggle Jennings]

Shin at the it actually ricocheted underneath the car I believe and hit Me in the shed.

[Morgan]

What does it feel like to get shot?

[Struggle Jennings]

You don't realize you get shot at first. Like, you don't feel it. You feel the pressure of the tug. But when you're in the moment with adrenaline, you don't feel it like that.

[Morgan]

And this was that when you were wrapped up in things back then?

[Struggle Jennings]

Oh, yeah. 100. From the time I was 12. Always went through phases because I always knew better. I'd been planted those seeds by my mom and my grandma, heavy in church and. And I had always been planted. Had seeds planted of right and wrong, but I just tugged away from it so much. And so I went through phases like 12 to 15. I was just wild. Went to move in with my uncle, was doing good for a little while, was like, yeah, I'm changing my life. Got caught back up. Went to jail when I was 21 on a weed case. Did 15 months, got out, walk straight for five years raising my kids, and then always diverted back to it when things got tough. It was like a comfort zone for me. Like, I knew I was good at being bad.

[Morgan]

Yeah, you. And you knew there was money. You knew there was a way to help you survive.

[Struggle Jennings]

Yeah, yeah. Temporary money.

[Morgan]

Yeah.

[Struggle Jennings]

Like, even at the height of my career in that world, even if I was making hundreds of thousands of dollars a month, when you're living that life, you don't really get to enjoy it or spend it. It gets spent for you. Like, you're making your friends bonds or you're paying for this funeral or you're. Somebody robbed somebody and you gotta. Jurors and you gotta. So it's like, there's always. Or you get busted and they take everything and you start.

[Morgan]

It was like money that kind of felt like not yours. You just actually do anything.

[Struggle Jennings]

It's an illusion. And that's why I try to tell a lot of these young guys now when I go into these prisons and talk and stuff is like, it all looks good. But my uncles told me when I was young, and they were caught up in a lot of the same things, too. But they told me when I was young, they're like, man, there's really only. You never really retire from this. You either end up dead or in prison.

[Morgan]

And so was 21 your last one?

[Struggle Jennings]

No, I just got home nine years ago. I did five years from 31 to 36. I did five years federal prison and state prison. Came home in 2016, was in a federal halfway house for six months. Got out, me and Jelly started touring. Jelly was just starting to get on his feet. He had been putting in a lot of work, but he was starting to catch a little bit of steam. And that was still five years before. And we did a few albums, did four albums called Waylon and Willie and.

[Morgan]

Just obviously inspired from your grandfather and.

[Struggle Jennings]

Their friendship and the, the two dualities of the two guys.

[Morgan]

And did you feel like you and Jelly were Waylon and Willie?

[Struggle Jennings]

We still are. We still are to this day. 100. Does that say the more stories I hear? Even now I'm like, God, this is crazy.

[Morgan]

Yeah. Like the outlaw side. And just the things you guys have experienced are more personality.

[Struggle Jennings]

Both. Both. All the above really. It's.

[Morgan]

Wait, so who's whaling and who's.

[Struggle Jennings]

Oh, I'm whaling. I'm hard headed. I still wear a hat that says cma. Country my ass.

[Morgan]

And what makes Jelly Willy?

[Struggle Jennings]

The light heartedness. He smokes a lot of weed.

[Morgan]

Like I'm following. I got.

[Struggle Jennings]

Yeah, there's a lot of, there's a lot of things. And he's been incredibly successful and he moves really good in that world and he's, he's just, he's done so much. I'm proud of him.

[Morgan]

And you get out nine years ago and what has been this stint that's kept you on this path to hopefully never go back?

[Struggle Jennings]

Let's talk about it, Morgan.

[Morgan]

Yeah, so tell me.

[Struggle Jennings]

When I went to prison, the mother of my kids fell really hard. My wife at the time, she got addicted to drugs, ran off with one of my best friends at the time. He ended up getting locked up. She got in a relationship after relationship with people that were using drugs and doing drugs. And she just went down a really dark path. Ended up losing custody of my kids. Before she lost custody, it got super dark. There was a time my daughter, innocence, she. She was three when I went four when I went to prison. By the time she was like five, six. I'm calling from prison. Her brothers and sisters haven't ate all day. It's five o' clock in the afternoon. Her mom's passed out on drugs. I had to teach her how to make macaroni and cheese from a jail phone so she could feed her siblings. And it was just thing after thing like that where it just struck that core that I was like, this cannot be how the story is told. This is. Can't be what I leave my kids. This can't. I can't. I know where they're headed with the environment they're in and what they're going through right now. And it's Not a pretty future. My daughter was molested in a drug house. They ended up in foster care. Their mother passed away from a drug overdose. That little girl just graduated with a 3.9 GPA honors.

[Morgan]

Oh, yeah. That's amazing.

[Struggle Jennings]

I love telling that when I say it on stage. Like, that's probably the loudest the crowd gets for me all night. But that's okay.

[Morgan]

You're like, that's okay. I'll take that.

[Struggle Jennings]

Yeah. Yeah, but. And all my kids are just thriving and doing so good. But I really. When I was in there, I had to really take full accountability for all of it. I was like, I'm the one that left them out there with a father. I left my wife out there without a husband. I left my mom without a son. I left my friends without their friend. Because I was the provider for a lot of people and always took care of everybody.

[Morgan]

And was that your wakeup call, just hearing that phone call?

[Struggle Jennings]

Yeah. And I never really had a chance to go back to sleep because it was every day I was getting a call like that. And then meanwhile, Jelly's out on a. In a van, sleeping in a van, touring. And every time I call him, having that little bit of hope of him going, man, this shit's really happening. We're out here. I'm in Tupelo tonight. I'm in Kansas City tonight. Or I'm here. So, like, hearing that, knowing, okay, this is possible. I can't control what's going on out there. The only thing I can control is what I do with this situation and who I become and who I come out. And so I just started stripping away all those layers and figuring out what are the thinking patterns that keep bringing me back in here? Why do I keep going back to the same thing? Why do I keep making the same mistakes and decisions? And I had to process a lot and figure it out. And so I came out a completely different person. I had lost 120 pounds. I rid myself of a lot of irrational thinking and beliefs and things that I was instilled through music and environment.

[Morgan]

And was that hard to rewrite? Especially as you're sitting in a prison where you're surrounded by people who have similar minds in a way. Was that hard to rewrite that entire story for you to come out a completely different person?

[Struggle Jennings]

A thousand percent. But the thing about it is 99 of people have it in them, and they want to change and they know better. It's just. Change is scary. And I was beyond the fact. The point of fear, my fear had Diverted from change to the end result of what was going to happen to my children. I just saw something the other day. It was like change happens when the reality of the outcome becomes scarier than the fear of change. Something like that.

[Morgan]

Essentially. What was happening exactly in these moments? How long, like when you were getting those phone calls, how much longer did you have to serve before you were able to get out?

[Struggle Jennings]

Oh, it started as soon as I got in there. It started happening as soon as I was away. Call home. And the first call is, oh, this happened, I'm so sorry. And then it's like you can just see the it getting worse and worse. And as soon as I hit prison, I walked in and I saw the different types of people, right? And you have the group that's still gambling, smoking, doing drugs, eating honey buns, sitting there watching TV all day. And then you got the guys that are getting up, going to classes all day, going to the yard to tr. Staying in shape and they stay in packs. And I was like, that's what I want.

[Morgan]

And you went to the pack that was going to the classes and working out.

[Struggle Jennings]

Yeah, I took the club, would take the classes so many times that I would be the teacher.

[Morgan]

And what are the classes like? What are these classes?

[Struggle Jennings]

You're like parenting and you have finances, critical thinking. I did all the drug programs, anti violence programs, just trying to learn how to reel your anger in and catch it before it gets anywhere. And I just rational self analysis type stuff and.

[Morgan]

But that was all a choice. You weren't required to go to any of that.

[Struggle Jennings]

Not at all. The drug program, you get time off if you take it. So of course there's an incentive to that. But I knew I needed it and I did it in the state, made parole in the state, but then I had to go serve my fed time. So then when I went to the feds and I went to do the program again because it would take a year off your sentence and you'd get six month guaranteed halfway house. So you're literally getting out 18 months earlier if you do the drug program. And I had five years, 57 months in the feds and a 13 year sentence in the state. But then the second time I went through that drug program, already knew all of it because I had taken the same program in the state. So I wasn't having to learn anything. I was getting to digest it. So the second time I went through the drug program, it like light bulb struck and I was like, okay, I got this.

[Morgan]

Yeah, that first time it was okay. This is all information for the first.

[Struggle Jennings]

Time, and I have to learn it. Learn it, write it down, take a test once. I've already learned it. I know I passed the test. I'm really learning it. It's really soaking in at that point. I'm really understanding it.

[Morgan]

So struggle now. Obviously, this is nine years ago, but you now, do you look at your life and you see your kids thriving, and you see you doing music and doing the things that you would talk to Jelly when you were in jail and he was doing. Do you look at your life now and you're like, dang, I did this.

[Struggle Jennings]

Yeah. But I still look at it like, man, I need to do better every day. I fall short of something. I could jump to conclusions and be like, I should have sat on that a little longer. Or. Or I could shift the blame and be like, man, I can't do that. I really got to take accountability for that. In relationships, in business, I still make a lot of mistakes, but I'm having to, like, really sit back and just learn how to remind myself of who I was when I came home. Because it's so easy. It's so easy to come out of prison and be like, oh, I got this. Watch this, and be this great person. And then life really starts happening. Life starts life in. And you'll fall back into old ways or you'll start to slip. And it's just about readjusting yourself every day. And really, prayer helps me a lot, especially with anger, because I'll just assess the day. Somebody might have said something to hurt my feelings, I might have done something to hurt somebody else's feelings. And I just gotta be like, look, I can't let the sun set on my anger. Pray about it, give it to God, and wake up and start fresh the next day. And that's really. With that and things like staying in a good routine with the gym, a lot of community work, a lot of going into jails and rehabs and speaking. And we're opening rehabs across the country right now called Sound Sobriety, where we're implementing songwriting in as me and Bradley Gilbert and a business partner named Michael Fry and his wife. And they were implementing songwriting into their therapy, teaching them how to put their feelings and their emotions and their testimonies in a song form.

[Morgan]

Can I ask you this, too? Because I imagine growing up in the ways that you did, you were not taught to share your feelings and emotions. You were probably taught, that's not what you do.

[Struggle Jennings]

And, yeah, so the men in my life, of course, Were like that. You don't cry, you don't tell anybody how you feel, or you hold it in, you be a man, you suck it up. But I was raised by a single mama that cried every day where she.

[Morgan]

Really went against that.

[Struggle Jennings]

Yeah, I'm a mama's boy. Like the wrong commercial. Come on. I'm balling like a baby. And then even as a father, you have. Now I see why the men told me that. Because there's a lot of time as a man, especially as a father or a husband or a friend, you have to. You want to shield them from knowing how bad it is sometimes. So you got to hold it in and deal with it sometimes. Because if everybody's looking at you as the breadwinner, the protector, the provider, the security, you can't let them know that everything's in shambles and you're trying to figure it out.

[Morgan]

Do you feel like that healing has started to reverse for you now? Like where you got. You got out and you were doing all this stuff to bounce back your life? Are you now at the point where you're able to look back on all of it and start to heal your inner self of stuff that was happening?

[Struggle Jennings]

Yeah, for sure. And, like, when the mother of my kids died, I wasn't able to grieve for a year, right. Because my kids were grieving really heavy. And then I lost the right behind it. We lost the father to my two step kids. He died of the same way. So between those two and then other friends and stuff, sometimes I've had to put my grieving on the back burner. And I've learned that's not always healthy. Like, you have to separate yourself, and you got to go find your own time to grieve. Whether it's an hour car ride, punching the steering wheel and screaming at God, whatever it is, praying and crying and whatever that may be, because I'm dealing with it right now. I'm wearing these two necklaces today because one of my best friends, Nemo, is actually fighting for his life right now. And I just had these made for us and was going to gift him to him. He was supposed to come down this week and stay at my house, and I didn't get a chance to give him to him, but he's fighting right now. And I had one of my best friends and workout partners pass this morning. I've had to take. I was just on vacation when I heard. When I got the news about Nemo. And he wasn't an artist or singer, but he was an Incredible singer and a songwriter, but he's just a biker. But he. We had got him to record a song that he had wrote. And so I literally had to like, we're on family vacation. I had to break away and go, hey, y' all just need a little while. And literally went there and turned that song on repeat and cried like a animal for two hours in the shower. And then came out, was like, all right, let's go. Gotta find that time to grieve. And I'm learning that life is. You're always a student and I'm always learning things.

[Morgan]

What do you feel like are some of your hardest lessons? Because I was going to ask you about grief because I do feel like, unfortunately you are no stranger to grief. Which sharing that of you getting in the shower and crying, I think is a good lesson for a lot of people. Because grieving tends to be one of those processes. We just push back and do what needs to be done to get through something.

[Struggle Jennings]

Yeah, you try to be too tough, you'll find out how weak you really are. Try to hold that in and then you're just gonna. It's gonna spill over and you're either gonna lash out or you're gonna break or. You gotta allow yourself to feel. You gotta allow yourself to release. You gotta allow yourself to feel those emotions. The older I get, the more I realize real men cry and they gotta. We have emotions, we got feelings. We gotta let it out. Yes. We gotta do it in our own time a lot of times. Because when you do have the women and children of your house and your friends and everybody looking at you for that strength, you got to be strong for them. But also when I was going through that, all my daughters came up to me and would put my arm, their arm around me. I came back, they knew that I was dealing with it, but I still just put the smile on and we finished family vacation.

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[Morgan]

How are you? I can only imagine how great of a girl dad you are.

[Struggle Jennings]

Oh, they're my baby.

[Morgan]

I need to know like girl dad struggle. Yeah, I'm hearing all like tough struggle right? Yeah, I need girl dad struggle.

[Struggle Jennings]

I've got four daughters and yeah, they're I love my sons. Don't take it wrong. They're my little mini me. I'm a little tougher on my boys because I want them to be good men. I want them to love and cherish the women in their life that was one of the last things my dad told me. Like, it's your job on this earth as a man to protect and provide for the women in your life. Never put your hands on a girl. So I'm super tough with my boys about their manners, chivalry, and raising the.

[Morgan]

Next generation of men.

[Struggle Jennings]

Yeah. I tell people all the time, I don't want to hear none of y' all complaining about the way this country is. If you're not raising your kids to fix it, if you're not raising your kids to be the next generation and to do better than we did, then you're missing, you're dropping the ball. But yeah, my girls, I have the best relationship with my daughters. We text and talk every day. We got a 25 year old named Brianna Harness.

[Morgan]

Wow.

[Struggle Jennings]

She's my firstborn. She's a blue singer. She's got an incredible voice. She's just dropped, I think, her fifth album. Wow.

[Morgan]

And she's 25.

[Struggle Jennings]

Yeah.

[Morgan]

But she's done more than I have and I'm 31. Hot damn. Okay.

[Struggle Jennings]

She works 10 hours a day on a farm. Wow. I think four days a week. And then cleans houses the other days. She's like, really independent as far as she only calls me when it's an emergency for money, which I. She knows I'd get her anything she needs and always be there, but she's really crushing it. And then my daughter, Innocence, she's dating a professional boxer named Austin Dulay, who I've known forever. He's a good friend. I'm great friends with his dad. And then I've got a daughter, courtesy, who's 17 and she's straight a student. She. I think her lowest grade was a 98. She had like 104s and stuff is insane. But she gets up every morning, goes to the gym, 5:00am, does Bible study, goes to school, gets off school, goes to work, and sometimes goes back to the gym. She's got a great relationship with her boyfriend. He's like number one in the state in soccer. And just you hear her talk and she's got it figured out more than I do.

[Morgan]

Okay. I need to know, like, having your. Having them meet the boyfriend situation for the first time. Because when I first met you, I was like, oh, dang. Like, he's gonna. He's been mean, tough, whatever. And then you're just like this teddy bear who's pulling snacks out of his backpack. Polar opposite. But when they first meet you, was it like, oh, crap.

[Struggle Jennings]

Oh, yeah. And I've already Got a reputation from the previous life before and then being a rapper and then a country singer. And I've got a checkered pass and live in a really nice neighborhood. So I'm already like that dad. And I'm the type that's. No, he's not picking you up. He's gonna knock on the door.

[Morgan]

Yeah, but you're making sure your girls are treated with princess treatment as they should be.

[Struggle Jennings]

Yeah. And they know whatever you do to her, I'll do to you. But I've had a couple that I kind of had to tighten down on. But for the most part, I raised my daughters to not settle. And by giving them an example of I'm not perfect. I definitely want my daughters to find somebody way better than I am. But they see the way that I am in my relationship and they see how I am as a man. And so they, they could. They have a. There's a bar that they can't go under.

[Morgan]

So that you're telling me that they don't have the bar in hell that some of us had.

[Struggle Jennings]

Yeah.

[Morgan]

In our 20s. Got you.

[Struggle Jennings]

Yeah.

[Morgan]

Proud of that for them.

[Struggle Jennings]

Yeah. And then I got a daughter, my stepdaughter, Patience. She's like our wild one. She's incredible.

[Morgan]

Is she the youngest of all of them?

[Struggle Jennings]

She's the young. She's not the youngest kid. Cuz we have two boys that are younger than her, but she's the youngest of the daughters and she's just herself. Like she chops her own hair off. She wants to be a. A hairdresser. So she's constantly her. You never know when she walks out of that room, you never know what color her hair is going to be and the next day. But it's always fashionable and she looks good. She pulls it off. She gets in a little bit more trouble at school, but it's because she doesn't take any. Like, she's just, she's. She's like real. I don't want to say stubborn. There's something else. All my kids have been through so much. Like she just lost her father, her biological father, to an overdose. And my kids lost their mother. And then my two oldest kids, my son, little Will, and my daughter Brianna, their mom, she went through it. She was a dancer and was on drugs and went to federal prison and. But now she's three years clean and sober, doing good, getting her life back in order. My kids still went through a lot with what I put them through, what their mothers put them through. And so there's a sense of resilience and just strength. If you met courtesy. First she pulls up in her little Lexus. In the first couple minutes, you're like, oh, this girl comes from money. And then you start having a conversation. You're like, oh, no, she's been through some. She just wears it really well, and she's learned from it. I got two beautiful young boys, 14 and 13, and one's into boxing, one's into football, and they're both doing good in school.

[Morgan]

And so you're telling me outside of all the tourists and all the stuff that you're doing, you're full on dad over here.

[Struggle Jennings]

Oh, yeah, definitely.

[Morgan]

And you really could be PTA dad if you wanted to.

[Struggle Jennings]

Oh, man, I would love to, too. I would love to go in there and tell them how to get it.

[Morgan]

Right, do all these things. This is what I suggest. Bringing the fruit snacks. I can totally see you bringing fruit snacks.

[Struggle Jennings]

I love fruit snacks.

[Morgan]

You do? With. You also brought the bubble gum. What was it?

[Struggle Jennings]

Yeah, you can't go on a baseball field. A big league, too.

[Morgan]

I like Da da tro. I feel like this needs to be a thing.

[Struggle Jennings]

Yeah, for sure.

[Morgan]

You have so much of that musical touches in your life. You mentioned it in your daughter's pursuing it. What was that like for you? You take away all the other things that you were experiencing in life, but you were the grandson of Waylon Jennings. Jesse Coulter. You. Your uncle is Shooter Jennings. You mentioned in just multiple different assets, how you just have all these different connections to different things.

[Struggle Jennings]

No pressure.

[Morgan]

Yeah. What's that like?

[Struggle Jennings]

Well, that's why I became a rapper, because I wasn't gonna try. My mom is an incredible writer and singer, and I grew up in a house with a piano. And whatever I was going through when I was little, my earliest memories was her waking me up, going, come on, we got to get ready for school. Come in the living room. And I'd come in the living room, she'd be, this is the day. This is the day that the Lord has made that the Lord. And she'd be playing hymnals and getting me up, and I'd be dancing. And so, like, music was always. But I had such. I had boots that I could never fill. Like, I could never be Waylon Jennings, but I can do the out of Struggle Jennings. And that was something Waylon taught me early. He's. Don't try to stand in my light. Don't stand in my shadow. Step outside and find your own light. And be yourself. So always be yourself Regardless what you're Going through. Stay true to what you're going through to yourself and your music, because there's millions of people going through the same thing that you are and that feel the same way. And you may not be everybody's cup of tea, but you'll be somebody's cup of coffee.

[Morgan]

That's some great advice to get from Whan. But also as a listener and a fan of country music, we know Waylon for outlaw country. We know the music that I sing about. We know what he sung about. Was he, like, that tough exterior on you as a grandson, or was it just a different person?

[Struggle Jennings]

Waylon was Whelen, and he definitely had. He was always whaling, he was always tough, but he was so loving, and he was such. Such an incredible. He was more like a dad to me because when my dad got killed, I went and stayed with Waylon for a while. I didn't go back to school that year. I took the last half of school off. And Whalen told the school he'll be back next year. It was like, he'll be back and he'll be in the next grade. Got it.

[Morgan]

You had somebody that was really having your back, not just like a normal having your back.

[Struggle Jennings]

Oh, no. Because he was. He was really that guy. Like, he was firm, he was tough, but he was so loving, and he made me feel like I was the coolest thing on the planet. I was only grandson that lived in Nashville for a long time. Way moved to Nashville and his brother moved to Nashville in their teens. So I, like, grew up in the house. Shooter was, like, a little bit more sheltered because he was in the house all the time.

[Morgan]

Different lives.

[Struggle Jennings]

Yeah. So I was, like the one that was coming from the outside in, like, first cigarette, showing him his first porn magazine. I was the bad influence because I was out there in the real world and. But Shooter, he left home at 18 to go have a rock band in LA and never left L. A. And he had his own dark path and overcame all of it. Now he's crushing it. Grammy after granted Grammy, between Brandy Carlisle and Tanya Tucker, and he just. He's producing all the Charlie Crockett stuff now. And Jake Owen just went and did a record with him, and I got a record with him coming out next year. So he's just. He's crushing it. I'm. Shooter's probably the best human being on the face of the planet, in my eyes, besides my. My beautiful little daughters.

[Morgan]

And when you were a kid, too, I was imagining that you don't really know any different. This is Just your family. This is your life.

[Struggle Jennings]

Yeah.

[Morgan]

So what. At what point did you realize.

[Struggle Jennings]

Yeah, when you get it in school, like, when you're in school, school, they'd be like, oh. They would try to use it against you.

[Morgan]

Is that why you turned away from it originally? I know you said that you didn't want to use the name.

[Struggle Jennings]

Yeah, because I always wanted to make money. I was friends with Yellow Wolf for probably a year and a half before I told him my grandpa was whaling. And the night that I did, he was like, what? Do what? And we're, like, drinking downtown Nashville, riding, listening, and we were listening to a whaling song. And I was like, he was my grandfather. He's like, what? Turn right around. He's like, what? And then he looked down. I've got this big watch on, this big expensive watch because I'm a drug dealer. And he's like, you're wearing a watch like that? And I said, you're right. Threw it out the window on Broadway. He still tells that story. But, yeah, and I just. I had always gravitated towards rap because that's the era that I grew up in. That's the environment that I grew up in. That's what spoke to me. But I loved country, and country was always the backdrop. Whan and George Straight, I know just about every word to every George Straight song. And then being on tour, hearing the instruments and the steel guitar, like, crying, and I always loved it. That's why I was really, like, the first one to ever put steel guitar on a rap record. In the early 2000s, I was the first one that started blending the two genres. Besides, of course, Bubba Sparks had a lot of country flavor in there. Timberland was in the beats and stuff, and Bubba's accent and the Tim McGraw and. But I was already mixing rap records in my bedroom with country at that point when that came out. And then a lot of people were like, oh, you can't mix country and rap. You're going to ruin your career. And then I went to prison and came home after I dropped Outlaw, went to prison, came home, and it was like a whole new genre.

[Morgan]

Was that weird, too? You drop an album, you're like, oh, I can't wait to promote. I can't wait to sing about it. You go to jail.

[Struggle Jennings]

Yeah. Dropped the song and then went to jail. Actually, the day I dropped the video, I went to jail the same day. And then I was gone five years. About a year and a half into my sentence, we dropped the whole album.

[Morgan]

So were you making phone calls? From jail and dropping the album.

[Struggle Jennings]

Yeah. So I had one of my best friends in the world, and he still works with me, does all my content, shoots most of my videos. And he's like my right hand man, Sebastian. He. He actually had signed me to a label deal and then his father had passed away and he. I quit hustling and all this. And then he like disappeared because he was having to deal with his grief and get his family right and make sure his mom didn't lose her house. And so he stepped away. And then when he called me back, he's like, man, what are you doing? I'm like, she got indicted. Looking at a bunch of time. And he was like, dude, I'm coming down there. And we recorded I Am Struggle, which was all whan samples and then me rapping to it. And that was the album that Outlaw was on. But we recorded it right before. It was like a rat race to get an album done before I went to prison because I didn't really know how much time I was looking at.

[Morgan]

Holy crap. I didn't know that about that record.

[Struggle Jennings]

Yeah. And it actually released while I was sitting in a prison.

[Morgan]

When you had fans over this course of your career. So was that also weird because you're like there and you're not really getting to do or have any interaction with what's happening with your music.

[Struggle Jennings]

Yeah, but like, the guards would come in and be like, man, we're listening to your song out in the parking lot. And then people would come in and be like, oh, man. And then especially being on five years, so about a time I'm in there three or four years, the song's gotten big, so new people coming in are like, oh. So it was cool. I was getting a feeling. I was getting a lot of fan mail in there, which gave me a lot of inspiration and hope. And I perfected handwriting.

[Morgan]

Were you songwriting in ever when you were there?

[Struggle Jennings]

So when I went in there, I started scribbling a bunch of lyrics and stuff. And then I was like, you know what? I started to notice that everything I was writing was from a perspective being in there. And I was like. As I was changing, the narrative was changing. So I was like, you know what? I'm not even going to try to do this. I'm gonna sit in here the next three years because I was like writing the first two. I was like, I'm just gonna absorb, and then when I get out, I'm gonna tell the story. So as soon as I got out, Yellow Wolf put me in the Studio. And I wasn't supposed to be recording because I was in a federal halfway house, so I had to have a real job. So Yellow will put me on payroll as the merchandise marketing director. And I had a little fake desk set up with a laptop that didn't even work in the corner of the studio in case the parole would come and have to check out my little area. And I was in there writing songs and recording.

[Morgan]

Little workaround. But you were working. It's just not probably an official version of what work looks like.

[Struggle Jennings]

Yeah. So they were gonna violate me and send me back because I was putting up these documentary episodes, and they were like, this isn't a real job. So they were about to send me back. They came and told me. They said, hey, you're going back to prison. This lady came in. She was on fire. She was like, I'm sending you back to prison. And I think, oh, this is BS you need to get a real job. This isn't a real job. And then they tell me, I'm going. So I packed all my stuff. Dr. March, say goodbye to my kids. After being gone all this time. And they were in a foster. In foster care at the time. I had to say goodbye to them again. Woke up the next morning, and they were like, hey, we need you to come downstairs. I thought Marshalls were there to pick me up and go in there. And that lady was like, I don't. Somebody called, and I guess you got somebody on your side, but we're putting an ankle monitor on you, d. And you're going to do this, and you're going to do that. And I was like, oh, I'm not going back. And then she leaves, and the director of the halfway house calls me in there, and he puts me on speakerphone, and it's the lady that's over all the programs, and she's like, dude, I love your documentary. She's like, I'm gonna start using it because greatness is in the gray area, and we've been black and white for so long. She was like, I'm gonna allot you eight hours a week of studio time, but you got to keep your job, and you got to bring your pay stubs in and pay your fees. We got an ankle monitor on. She was like, that's the only way that I could really justify not sending you back. And she really. She helped out a lot.

[Morgan]

And.

[Struggle Jennings]

Wow. So I ended up not going back.

[Morgan]

It just took that one person.

[Struggle Jennings]

That one person to just believe and go, okay, this guy really has the opportunity to make a change. And. Yeah.

[Morgan]

Wow. That's a really cool story.

[Struggle Jennings]

I'm glad.

[Morgan]

That was not where I anticipated it going, but that was really cool.

[Struggle Jennings]

Yeah.

[Morgan]

And also awesome. Just that there was that one person out there who said, I'm gonna do things a little differently.

[Struggle Jennings]

Yeah.

[Morgan]

Because it always takes one person to make a change. I know sometimes you do everything monotonous and stay in the black and white, as she said. Because that's what you mentioned way before any of this. Is that change is hard.

[Struggle Jennings]

Yeah.

[Morgan]

Making that change is hard. And she just chose. And it's really cool. That made a point in your story. So all of your music. I know we've talked about all the personal stuff, and I think I could sit here and talk to you all day about all of the things in your life, but two things. Your music. How many albums do you have?

[Struggle Jennings]

I probably got, like, I'd say 13 or 14 out there, but I've got. I have 85 now unreleased songs.

[Morgan]

Crazy.

[Struggle Jennings]

I'm about to release first single drops Friday for me. And Brian Martin did an EP called 1976. He just got kicked off the Morgan Wallen Tour, and he came over. We were meeting for the first time, gonna write a song, and ended up with a bottle of whiskey and telling me everything that was going on in his life. And I said, man, let's do an album together. He was, like, getting blacklisted and stuff at the time. And I'm like, I like you. And so we sat in there five days, wrote five songs, brought all the band in one room, let him rock. We laid the vocals all super old school. Got a just a real authentic feel. It's called 1976. The album is. And it comes out October 3rd.

[Morgan]

Wow. And that's the latest.

[Struggle Jennings]

September 26th.

[Morgan]

Okay. That's the latest album of all of these.

[Struggle Jennings]

Yeah, yeah, that one's coming out. And then right behind it in November, I have my album Last Name, produced by Ned Cameron, who's incredible. He produced Only God Knows with me and Jelly. And a couple songs off my last album. I've got a full album that's coming in November from. Produced by him. Then I've got two more rap albums that are finishing up now. And I've got the album produced by Shooter. It's done. I gotta go relay a few vocals because I got with a vocal coach. I was like, I'm gonna take this serious. Being a rapper so long and my heartbeat in country music and wanted to go to switch completely over the country was originally my idea. I Just jumped in with a vocal coach to just really learn and perfect it and find my voice and be able to use it.

[Morgan]

How do you have time to sleep and be a dad when you have four actual albums that are happening all in the span of the next.

[Struggle Jennings]

Even more than that, because I got another one that we're recording in August. It's all old school. I wrote a bunch of songs with like Bob Dapiro Row and a bunch of old school writers that just. It came out and it was so different than the other stuff that I had that I was like, oh, we got to put this on a project. So me and a good friend of mine, Zach Garner, who's. He co produces a lot of things with me, and he's incredible. So we're doing that in August. And I wasn't. I was kind of chasing for a little while the country radio thing. I was like, man, we would. All. Growing up as a kid listening to the radio, you want to hear your stuff on the radio. But there's a lot of steps involved to that. But I was really getting the whole, you got to completely commit to country and you can't put out any more rap. And then Bradley Gilbert was like, bubba, you can't forget to dance with the girl that brought you to the party. And I can't not rap. That's.

[Morgan]

That's part of who you are.

[Struggle Jennings]

Yeah, it's part of who I am. So I was just like, you know what? As much as I would love country radio, maybe one day I'll get to hear my songs on the radio. But I'm not going to chase that. I'm not going to. I'm going to just keep doing exactly what I'm doing. I'm going stay independent and I'm going to keep pumping these albums out. The hard part about being independent is a lot of times you don't get the push and you don't get the promotion and the marketing that you would get if you were on a major label. But some songs, it could be number one on country and they get looked over, but they become other people's favorite songs. Like 50 Times a Day, I get comments like, why is this not number one in the country? But I just. I like to still be able to go into Kroger and shop. My community loves me. I love to be able to pull up at the kids football games and.

[Morgan]

And there's a lot of beauty and independent that you get to put out what you want to put out and do the projects you want to do. You have so much more drive to do it too. So I think it looks differently every. We talk about this a lot. That fame is so shifted. And yeah, you can have a successful career any which way as long as you go for it. Really?

[Struggle Jennings]

For sure.

[Morgan]

There's not one I want to do.

[Struggle Jennings]

It till I'm 90. I'm gonna be. I don't care if it's just. I don't. I was blessed to get to go do amphitheaters with Jelly Roll and watch that. Now he's in stadiums with post and watching all that. I'm so proud of him and. But there's moments where I'm like, man, I see the way he has to live. I see the way that. How busy he is and how much he does. And there's moments where I'm like, man, I would be blessed to be in that position. But also kind of like being independent.

[Morgan]

Absolutely. And I do love to end these things on a piece of advice. And I want everybody to go check out all of struggles music. I think you could listen to it for a whole entire year before you finally made it through everything.

[Struggle Jennings]

I'm drop a whole new catalog.

[Morgan]

Yeah. So get through all of that. But I like to end the podcast on whether it's a piece of advice or motivation or inspiration, something that maybe we haven't touched on. However, the floor goes to you. But that's what I like to end on.

[Struggle Jennings]

I've been blessed recently. I just got made the director of Send Musicians to Prison. Nathan Lee's been running it for 16 years, and they took me into Rikers island, and it was so special. I was like, man, I want to do this more and be a part of it. And Nathan Lee had just been to where he was stepping down from it and just stand on the board. And they were like, we're looking for a new director. And so they all voted, and I became the new director. And so I'm getting to go back into prisons. And one of the things that I find the most that I really is just on my heart to tell people is, don't let your past define you. There were so many times in life where people would ask me, like, are you ready? And I was like, yeah, I was born ready. But I wasn't born ready. I had to go through all the that I went through to get ready. And I like to use the analogy when they purify gold, they put it in a fire, they pull it out, wipe off all the imperfections, and they put it back in the fire. Don't be afraid of those flames. Anything you're going through, anything you've been through, it's all leading you up to where you're supposed to be. You just have to keep that mindset. You have to keep moving forward, make the best decisions you can and you will get where beyond where you can dream you would be in any aspect, whether it's success, business, relationships, love. Just keep moving and just lead with your heart and don't give up.

[Morgan]

Oh, that's a really confusing Congratulations on becoming the director. I think that's really cool. Yeah, obviously that's going to be a great way for you to get back in the community. It's cool that you're changing what would have been really beneficial and helpful for you. You're making sure that's happening for other people and I think that's really awesome.

[Struggle Jennings]

Well, I think it's better to focus on building something bigger than yourself.

[Morgan]

Absolutely. It's a whole. It's part of the reason why we're here. Right?

[Struggle Jennings]

Yeah.

[Morgan]

So struggle. Thanks for being here. Thanks for being so open sharing your story.

[Struggle Jennings]

Thank you.

[Morgan]

I told you guys this was a great one. I'm happy it's finally in your hands and if you liked it, please subscribe to the podcast and follow at. Take this person personally on Instagram for so much more content. Thanks for being here with me this week. As always, I'm happy that you're here and I can't wait for you to be here next week.

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[Struggle Jennings]

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[Morgan]

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[Morgan]

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