The Bobby Bones Show - MORGAN: Struggle Jennings On Getting Shot, Surviving Prison, and Carrying a Legendary Name

Episode Date: September 1, 2025

Struggle Jennings has lived a life few could imagine from surviving gunshots, serving time behind bars, and carrying the weight of being the grandson of country music icon Waylon Jennings. In this powerful conversation, he opens up about the turning points that led him from prison cells to packed-out shows, how he rewrote his story through music, and what it means to honor a legendary name while carving his own path. Follow Struggle Jennings: @iamstruggle Follow Morgan: @webgirlmorgan Follow Take This Personally: @takethispersonallySee omnystudio.com/listener for privacy information.

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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 follow. it 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. Thanks for having me. I got to carry that

trophy home that day. You did. I was supposed to give it to jelly and he never picked it up so it is on my mental. I love that. You're like, by 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. This is the dude. I do. It was going to be hot and I was going to have a lot of friends and just bring snacks for friends. You knew how to make friends. Like, you knew the momentum there. 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, I was 16 when she had me. 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. Very much stuff. And talk to me about your life and your childhood, which also, one of my questions, is struggle your real name or is this just a snage name? Okay. And why? What is struggle? Like, where did that come from?

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 of course, I had a name in the streets. But I was like, I don't know if this name is really digestible. I don't know if a parent's going to let her kid buy a CD from Little Killer. That was your name in the streets from Little Killer. When I was a teenager. Do you get that name or does somebody give you that name? Somebody gives it to you. And the same way with struggle.

A friend of mine, we were working. We were about to go do our first studio session. And we had been, like, practicing or writing the songs. And me and him were doing like an EP together. And I got him white boy. And he was like, man, he was like, what are you going to go by? I was like, man, I don't know. 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 go by struggle. And I was like, all right, cool. So I started going by.

At first it was like young struggle. Yeah. And as I got older, it became struggle. And then my grandfather being Waylon, when I caught my case, they automatically started calling me Struggle Jennings. They were 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 socialism. That was before Instagram or anything like that.

My Twitter is still a young strug. He was like, no, man, he was like, dude, if you Google struggle, it's going to pop up like kids in Africa and wars, all kinds of struggles that are like going on. He was like, Struggle Jennings. It'll be Google boy. I was like, man, I don't know. And so I called my uncle Shooter. And he was like, nah, Waylon would love that.

He was like, take that name and make it your own. And so I rode with it. By the time I came home, there was really no reversing it. It had already been done. You already became Struggle Jennings. And you just mentioned your mom. And talk to me about childhood because you talked about your friends and you went through a lot of struggle. Yeah.

What were some of those moments in your life that led to where you are now? Yeah. So, I mean, starting early, my mom was 16 when she had me. And she's the daughter of Jesse Coulter and Duane Eddy, who's a legendary guitar. player rock and roll and jessie and wayland 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 roughneck good old boy and they met at the west national skating rink and one starry night in the back of his el camino

I was made. You love to tell that story, don't you? Yeah. Yeah. I love it. I'm about as West Nashville as they get. So they lasted until I was about four. My grandpa bought them a house in Franklin in a neighborhood called Maplewood.

There was only like four or five houses when he bought the house. And it was like a 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. 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, 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 four. So she was doing it on her own, but she was still singing backup for Waylon. So she was gone a lot on tour And then in the summertime I'd get to go on the bus And I was at Waylon's house a lot

Because me and Shooter Are just a year apart Which is my uncle, though Yeah, that's Waylon and Jesse's only kid together Yeah 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 shit out of her And of course, my dad came over there and ran him off. But then when I was 10, my dad was murdered. I remember when we were talking before this, you had mentioned that.

And were you living with your dad at the time? No, I was living with my mom. Okay. 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'll call him back later. And then when I came in that night, she was crying in the back room.

all of a sudden, Wayland, 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. Were they telling you that to protect you, 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 had been living with my uncle because I started getting in a lot of trouble. 12, I joined the gang, started selling drugs. My mom had her and Wayland 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. I think you should chill a little bit. And she's 20-something-year-old young lady looking for love and on her own and alone. And she's gone through a lot of stuff at this point. Yeah, for sure. And so she kind of had that mentality, you know what? I don't want your money. I don't need your help.

I'm going to do it on my own and I'm going to show you that I can do it on my own. So it was like a culture shock. 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 them and she was trying to prove. So we went through from what seemed like a pretty normal childhood. I'd be at West Nashville on the weekends a lot to see my dad or my uncle or my cousins and stuff. So I always straddled those tracks where when I was in West Nashville,

you know, I've 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 Wayland's house and see the Jag and the Cadillac and the maid and the nanny and the guards. These very two polarized lives. 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 with the drug dealers. So I always gravitated towards that because I saw a quality of life that I knew is 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. That kind of led me into being a drug dealer most of my life and in a life for crime.

That's really tough too. 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? Oh, a thousand percent. Like, I have no regrets in life. I mean, there's some things I wish I may not have said or a couple of 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, you know, I just. just it kept leveling me up to the place that I'm at now as a man. Oh, and I want to ask you because I grew up in rural Kansas.

There's not a lot happening over there. We got a lot of farmers in countryland. That's what I'm not in. Most people get in trouble is when it's boring is when you find shit to do. 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 cave, that was terrifying and you were doing and experiencing things that as a kid you never should have had to? For sure. I think that we were so caught up in the lyrics of Tupac and no limit and 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 never 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 was a time where I wanted to be Tony soprano I want to be John Gotti you really went through different periods I did I did.

Like eras of struggle. 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. 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. 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, I really just want to be home with the kids. Do I really want to be a huge country star or 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'm so embedded with just a love for music as my life to a point. My children are my life and my family, of course. But 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 of 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 a, a, you know, 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. Are you telling me that you've been shot before? Oh, yeah, I've been shot twice. I actually got shot. You know where Big Bad Breakfast is? Yeah. Okay, so that used to be Wendell Smith's. It was a corner store.

Okay, Wendell Smith is still there. The restaurant and the liquor store. Okay, okay. So Big Bad Breakfast was the convenience store. So old man, Wendell had the convenience store. the liquor store and the restaurant. My whole family worked in the restaurant. My aunt was a waitress there.

I think my dad bus table was 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 an old school gambler, like Southern mafia type guy. His son, Benji still runs. And then the grandson also runs the restaurant. Okay.

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

I don't care what you're saying. Yep, that's me. Clipper Taylor the 4th. You might have seen the skits, the reactions, my journey from basketball to college football, or my career in sports media. Well, somewhere along the way, this platform became bigger than I ever imagined. And now I'm bringing all of that excitement

to my brand new podcast, The Clifford Show. This is a place for raw, unfiltered conversations with some of your favorite athletes, creators, and voices that not only deserve to be heard, but celebrated. One week, I'll take you behind the scenes of the biggest moments in sports and entertainment, and the next we'll talk about life,

mental health, purpose, and even music. The Clifford Show isn't just a podcast. It's a space. For honest conversations, stories that don't always get told, and for people who are chasing something bigger. So if you've ever supported me or you're just chasing down a dream, this is right where you need to be. Listen to The Clifford Show on the IHeart Radio app, Apple Podcasts,

or wherever you get your podcast. And for more behind the scenes, follow at Clifford and at TikTok Podcast Network on TikTok. You can have opinions. You can have like a strong stance. And then there's your body. having its own program. I'm Dr. Maya Shunker, a cognitive scientist and hosts of the podcast, a slight change of plans,

a show about who we are and who we become when life makes other plans. We share stories and scientific insights to help us all better navigate these periods of turbulence and transformation. There is one finding that is consistent, and that is that our resilience rests on our relationships. I wish that I hadn't resisted for so long. the need to change. We have to be willing to live

with a kind of uncertainty that none of us likes. Listen to a slight change of plans on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. I feel like it was a little bit unbelievable until I really start making money. It's Financial Literacy Month

and the podcast Eating While Broke is bringing real conversations about money, growth, and building your future. This month, hear from top streamer, Zoe Spencer and venture capitalist Lakeisha Landrum-Pierre, as they share their journeys from starting out to leveling up. If I'm outside with my parents and they're seeing all these people come up to me for pictures, it's like, what?

Today now, obviously, it's like 100%. They believe everything, but at first it was just like, you got to go get a real job. There's an economic component to community striving. If there's not enough money and entrepreneurship happening in communities, they fail. And what I mean by fail is they don't have money to pay for food. They cannot feed their kids. They do not have homes. Communities don't work unless there's money flowing through them.

Listen to Eating While Broke from the Black Effect Podcast Network on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. Wait, and so you got shot where that place is now? Yeah, I got to shoot out there when I was young. How old were you? I got hit in the shin. It actually ricocheted underneath the car, I believe. And it hit me in the shin. What does it feel like to get shot?

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. And this was that when you were wrapped up in things back then? Oh, yeah, 100%. From the time I was 12,

I 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 I had always been planted, had seeds planted of right and wrong. But I just tugged away from. 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. I 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, walked straight from five years, raising my kids.

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

Temporary money. Yeah. 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 friend's bonds or you're paying for this funeral. or you're somebody robbed somebody and you got to jurors.

And so it's like there's all way or you get busted and they take everything. So it was like money that kind of felt like not yours. You just actually do anything with? Yeah, it's an illusion. And that's why I try to tell a lot of these young guys now when I go to these prisons and talk and stuff is like it all looks good. But my uncle 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 never really. You never really retire from this. You either end up dead or in prison. And so was 21 your last one? 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. I was in a federal halfway house for six months. Got out, me and Jellie started tour. And Jellie 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 Whelan and Willie.

Obviously inspired from your grandfather. And their friendship and the two dualities of the two guys. Did you feel like you and Jelly were Whalen and Willie in the way? We still are. We still are to this day, 100%. Does that same kind of vibe? The more stories I hear even now, my God, this is crazy. Yeah.

Like the outlaw side and just the things you guys have experienced or more personality side? Both, both. All the above. Really. Wait, so who's whaling and who's Willing? I'm whaling. I'm hard-headed. I still wear a hat that says CMA, country my ass.

And what makes jelly, Willie? The lightheartedness, he smokes a lot of weed. I'm following. I got to. Yeah. There's a lot of things. And he's been incredibly successful. And he moves really good.

in that world. And he's just, he's done so much. I'm proud of him. 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?

Let's talk about it, Morgan. Yeah, tell me. When I went to prison, the mother and 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 into 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 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 having eight 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 stories told. This 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. Oh, yeah. We love that. That's amazing.

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. You're like, that's okay. I'll take that. Yeah, yeah. 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. And was that your wake-up call? Just hearing that phone call? 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, jellies out in a van, sleeping in a van tour 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 and 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 start 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? What 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 had rid myself of a lot of irrational thinking and beliefs and things that I was instilled through music and environment. Was that hard to rewrite, especially as your sense? 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?

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 and the fear of change. Something like that.

And that's essentially what was happening to you 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. Oh, 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 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, honey, bun 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 train staying in shape and they stay in packs and I was like that's what I want then you went to the pack that was going to the classes yeah yeah I took the class I would take the classes so many times that I would be the teacher and what are the classes you like parenting and finances critical thinking I did all the drug programs anti-violence programs just trying to learn how to real your anger in and catch it before it gets anywhere and I just rational self-analysis type stuff but that was all a choice you weren't

required to go to any of that 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 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 months 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 program, it like a light bulb struck. And I was like, okay, I got this. Yeah, that first time it was, okay, this is all information for the first time. And I have to learn it, learn it, write it down, take a test. Once I've already learned it, I know I can pass the test. I'm really learning it. It's really soaking in at that point.

When I'm really understanding it. 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? 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 I could shift the blame and be like, man, I can't do that. I really got to take accountability for that in relationships and 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 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 lifeing. And you'll fall back into old ways or you'll start to slip.

And it's just about readjusting yourself every day. 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 got to be like, look, I can't let the sun set on my anger. I 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 gym.

jails and rehabs and speaking and we're opening rehabs across the country right now called Sound sobriety where we're implementing songwriting in. It's 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. 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. 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 hold it in. You'd be a man. You suck it up. But I was raised by a single mama that cried every day. Where she really went against that.

Yeah, and I'm a mama's boy. Like, the wrong commercial come on. I'm bawding 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. 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?

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 stepkids. 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've 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 who's 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 passed 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 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 and repeated and cried like a animal for two hours in the shower.

And then he came out, I was like, all right, let's go. You got to find that time to grieve. And I'm learning that. Life is, you're always a student. And I'm always learning things. 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. You try to be too tough. You'll find out how weak you really are. Try to hold that in. And then it's going to spill over and you're either going to lash out or you're going to break or you've got to allow yourself to feel. You got to allow yourself to release.

You got to allow yourself to feel those emotions. The older I get, the more I realize, real men cry. And they got to, we have emotions, we got feelings. We got to let it out. Yes, we got to do it in our own time a lot of times because when you do have the women and children of your house, 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. I would put my arm around me. When I came back, they knew that I knew that I, I was dealing with it, but I still just put the smile on and we finished family vacation. A win is a win. A win is a win. I don't care what you're saying.

Yep, that's me, Clifford Taylor the 4th. You might have seen the skits, the reactions, my journey from basketball to college football, or my career in sports media. Well, somewhere along the way, this platform became bigger than I ever imagined. And now I'm bringing all of that excitement to my brand new podcast, The Clifford Show. This is a place for raw, unfiltered conversations with some of your favorite athletes, creators, and voices that not only deserve to be heard, but celebrated. One week, I'll take you behind the scenes of the biggest moments in sports and entertainment,

and the next we'll talk about life, mental health, purpose, and even music. The Clifford Show isn't just a podcast, it's a space for honest conversations, stories that don't always get told, and for people who are chasing something bigger. So, if you've ever supported me, or you're just chasing down a dream, this is right where you need to be. Listen to the Clifford show on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. And for more behind the scenes,

follow at Clifford and at TikTok Podcast Network on TikTok. I feel like it was a little bit unbelievable until I really start making money. It's Financial Literacy Month, and the podcast Eating While Broke is bringing real conversations about money, growth, and building your future. This month, hear from top streamer, Zoe Spencer, venture capitalist Lakeisha Landrum Pierre, as they share their journeys from starting out to leveling up.

If I'm outside with my parents and they're seeing all these people come up to me for pictures, it's like, what? Today now, obviously, it's like 100%. They believe everything. But at first, it was just like, you got to go get a real job. There's an economic component to community striving. If there's not enough money and entrepreneurship happening in communities, they fail. And what I mean by fell is they don't have money to pay for food.

They cannot feed their kids. They do not have homes. Communities don't work unless there's money flowing through them. Listen to Eating While Broke from the Black Effect Podcast Network on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. You can have opinions. You can have like a strong stance. And then there's your body having its own program. I'm Dr. Maya Shunker, a cognitive scientist and hosts of the podcast, a slight change of plans, a show.

about who we are and who we become when life makes other plans. We share stories and scientific insights to help us all better navigate these periods of turbulence and transformation. There is one finding that is consistent, and that is that our resilience rests on our relationships. I wish that I hadn't resisted for so long the need to change. We have to be willing to live with a kind of uncertainty that none of us likes. Listen to a slight change of plans on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. How are you?

I can only imagine how great of a girl dad you are. I need to know like girl dad's struggle. Yeah, I'm hearing of a tough struggle, right? I need girl dad struggle. I've got four daughters. And yeah, I love my sons. Don't take it wrong. They're my little mini-meater.

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. There was one of the last things my dad told me. 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. They're raising the next generation of men. 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 have a 25-year-old named Brianna Harness.

Wow. She's my firstborn. She's a blues singer. She's got an incredible voice. She's just dropped, I think, her fifth album. Wow. And she's 25? Yeah.

She's done more than I have. I'm 31. Hot damn. Okay. She works 10 hours a day on a farm. Wow. I think four days of, weekend 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 Dule, 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 a straight-A student. I think her lowest grade It was a 98. She had like 104s and stuff. It's insane. But she gets up every morning.

It goes to the gym. 5 a.m. 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 state in soccer. And just you hear her talk and she's got it figured out more than I do. Okay. I need to know, like having them meet the boyfriend situation for the first time. Because when I first somebody I was like, oh, dang. Like, he's going to be mean, tough, whatever. And then you're just like this teddy bear who's pulling snacks out of his backpack. Yeah.

But when they first meet you, was it like, oh, crap? 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 of snow. He's not picking you up.

He's going to knock on the door. Yeah, but you're making sure your girls are treated with princess treatment. As they should be. 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 have a, there's a bar that they can't go under. So that you're telling me that they don't have the bar in hell that some of us had over our 20s? Got you. I'm proud of that for them. Yeah. And then I got a daughter, my stepdaughter, patience.

She's like our wild one. She's incredible. Is she the youngest of all of them? She's a young, she's not the youngest kid because we have two boys that are younger than her. But she's the youngest of the daughter. and she's just herself. Like she chops her own hair. She wants to be a hairdresser.

So she's constantly here. You never know. When she walks out of that room, you never know what color her hair is going to be 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 shit. She's just, 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. 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 shit. 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. So you're telling me outside of all the touring and all the stuff that you're doing. You're full on dad over here. Oh, yeah, definitely. And you really could be PTA dad if you wanted to. Man, I would love to.

I would love to go in there and tell them how to get it right. Do all these things. This is what I suggest bringing the fruit snacks. I can totally see you bring fruit snacks. I love fruit snacks. You do. You also brought the bubble gum. What was that?

Big League, you can't go on a baseball field without Big League too. I like a date. Dad trauma. I feel like this needs to be a thing. Yeah, for sure. You have so much of that musical touches in your life. You mention it and 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 Colter, your uncle is Shooter Jennings. You mentioned in just multiple different assets how you just have all these different connections to different things. No pressure. Yeah. What's that like? Well, that's why I became a rapper because I wasn't going to 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. 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. So, like, music was always,

but I had such, I had boots that I could. could never feel. Like I could never be Waylon Jennings, but I can do the shit out of struggle Jennings. And there was something Waylon taught me early, is 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.

That's some great advice to get from Whalen, but also as a listener and a fan of country music, we know Waylon for Outlaw Country. We know the music that I sang 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? Waylon was Waylon, and he definitely had,

he was always Waylon. He was always tough, but he was so loving. And he was 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 Whaling told the school, he'll be back next year. He was like, he'll be back and he'll be in the next grade, got it? You had somebody that was really having your back, not just like a normal having your back.

Oh, no. Because 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. 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. Different lives. 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. But Shooter, he left home at 18 to go have a rock band in L.A. and never left L.A.

and he had his own dark path and overcame all of it. Now he's crushing it. Grammy after Grammy between Brandi Carlisle and Tanya Tucker. And 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 crushed. I'm shooters probably the best human being on the face of the planet in my eyes.

Besides my beautiful little daughters. 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. Yeah. So what at what point did you realize? Yeah, when you get it in school. Like when you're in school, they'd be like, oh, they would try to use it against you.

Is that why you turned away from it originally? I know you said that you didn't want to use the name. Yeah, because I always wanted to make more. 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? Dude, 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? Turned a radio down. He was 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 it? And I said, you're right. Do it out the window on Broadway.

he still tells that story. But yeah, and I'd 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. Country was always the backdrop. Waylon and George Strait.

I know just about every word, every George Strait 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 early 2000. 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 Nellie's 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 make. country and rap. You're going to ruin your career. And then I went to prison and came home after I dropped out law shit, went to prison, came home. And it was like a whole new genre. Was that weird too? You drop an album. You're like, oh, I can't wait to promote it. You go to jail instead.

Drop the song and then went to jail. Actually, the day I dropped the video, I went to jail the the same day. And then I was gone five years. About a year and a half into my sentence, we dropped the whole album. So were you making phone calls from jail and dropping that 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 actually had signed me to a label deal, and then his father had passed away, and 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, I 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 whaling samples. And then me rapping to it. And that was the album that Outlaw shit 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. Holy crap. I didn't know that about that record. Yeah. And it actually released while I was sitting in a prison. When you had fans over this course of you.

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. Yeah, but like the guards would come in and be like, man, we'd listen to your song out in the parking lot. And then people would come in and be like, I'm in. And then especially being gone 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 shit. So it's cool. I was getting a fill it. And I was getting a lot of fan mail in there, which gave me a lot of inspiration and hope. and I perfected handwriting. Were you songwriting in ever when you were there?

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 going to sit in here the next three years because I was like writing the first two. I was like, I'm just going to absorb.

And then when I get out, I'm going to 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 Wolf 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 in my little area. and I was in there writing songs and recording.

A little work around, but you weren't working. It's just not probably an official version of what work looks like. Yeah, so they were going to 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 said goodbye to my kids after being gone all this time. And they were in a 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 to come downstairs. I thought marshals were there to pick me up. And go in there, and that lady was like, I don't, somebody called. I guess you got somebody on your side, but we're putting an ankle monitor on you, da-da, and you're going to do this, and you're going to do that. I was like, oh, shit, 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 going to 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 going to allot you eight hours, 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. And so I ended up not going back. It just took that one person. That one person to just believe and go, okay, this guy really has an opportunity to make a change. And yeah. Wow. That's a really cool story. I'm glad that was not where I anticipated it going, but that was really cool. And all. also awesome just that there was that one person out there who said, I'm going to do things a little differently. 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. 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 i probably got like i'd say 13 or 14 out there but i've got i have 85 now unreleased songs crazy i'm about to release

first single drops friday for me and brian martin did the EP called nineteen seventy six he just got kicked off the morgan walling tour and he came over We were meeting for the first time, going to 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 them rock. We laid the vocals, all super old school, got just a real authentic feel. It's called 1976. The album is, and it comes out October 3rd. Wow. And that's the latest. September 26th.

Okay. That's the latest album of all of these. 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 got to go relay a few vocals because I got with a vocal coach. I was like, I'm going to take this serious. Being a rapper so long and my heart-bending country music and wanting 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 to perfect it and find my voice and be able to use it. 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 six months? 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 like Bob DePiro 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 was kind of chasing for a little while, the country radio thing. I was like, man, I was, 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've got to completely commit to country and 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. It's part of who you are. 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 to 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 so 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 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. We talk about this a lot, that fame is so shifted. And you can have a successful career any which way as long as you go for it, really.

For sure. There's not a one pack. I want to do it until I'm 90. I'm going to 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. 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 I also kind of like being independent. 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've made it through everything. And I'm going to drop a whole new catalog for that time. 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. I've been blessed recently. I just got made the director of Send Musicians to Prison. Nathan Leesman running it for 16 years. And they took me under Rikers Island.

And it was so special. I was like, and 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 staying 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 this.

shit 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 beyond where you can dream you would be in any aspect, whether you're going to 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. Oh, that's 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. Well, I think it's better to focus on building something bigger than you. yourself. Absolutely. It's a whole part of the reason why we're here, right? So struggle, thanks for being here. Thanks for being so open sharing your story. Thank you. I told you guys, this is a great one. I'm happy it's filing your hands. And if you liked it, please subscribe to the podcast and follow at Take This 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. A win is a win. A win. A win is a win. I don't care what I'm saying. Yep. That's me. Liver Taylor the 4th. You might have seen the skits, my basketball and college football journey, or my career in sports media. Well, now I'm bringing all of that excitement to my brand new podcast, the Clifford Show. This is a place for raw unfilled conversations with athletes, creators,

and voices that not only deserve to be heard, but celebrated. So let's get to it. Listen to the Clifford show on the IHeard Radio app, Apple Podcast, or wherever you get your podcast. And for more behind the scenes, follow at Clifford and at TikTok Podcast Network on TikTok. Day May 2nd. Country's biggest stars will be in Austin, Texas. At our 2026, I Heart Country Festival

presented by Capital One. C. Cain Brown. Parker McCollum. Riley Green. Shaboozy. Dylan Scott. Russell Dickerson. Gretchen Wilson.

Chase Matthew. Lauren Elena. Tickets are on sale now. Get yours before they sell out at Ticketmaster. It's Financial Literacy Month, and the podcast, Eating While Broke, is bringing real conversations about money, growth, and building your future. This month, hear from top streamer Zoe Spencer and venture capitalist Lakeisha Landrum Pierre, as they share their journeys from starting out to leveling up. There's an economic component to communities thriving. If there's not enough money and entrepreneurship happening in communities, they failed.

Listen to Eating While Broke from the Black Effect Podcast Network on the IHeart radio app, Apple Podcasts, or wherever you get your podcast. This is an IHeart podcast. Guaranteed human.