Sunday Sitdown with Willie Geist - Jelly Roll on His Journey From Struggle to Country Stardom (October 2024)

Episode Date: August 31, 2025

Few artists have walked a path like Jelly Roll, who grew up surrounded by struggle and addiction before choosing redemption. In this sitdown from October 2024, Jelly Roll talks with Willie about his transformation from rapper to country star, the resilience that shaped his music, and the persistence that led him to selling out arenas across the country. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Hey guys, Willie Geist here with another episode of the Sunday Sit Down podcast. My thanks, as always, for clicking and listening along. Man, am I excited for you to hear my conversation this week with one of the brightest, most talented and honestly most inspiring stars in all of music right now? He goes by the name of Jelly Roll. His real name is Jason DeFord, but his mom gave him the nickname Jelly Roll many, many, many years ago. And it has stuck through his life and now through his rise to stardom. If you don't know Jelly Roll, look them up real quick. You'll know him right away. Big guy, face tattoos, big smile, lots of energy, lots of charisma and lots of talent as a musician. He actually started as a rapper and has evolved in the last few years to become one of the biggest stars in country music and really has transcended into popular music as well. You may know him because he just was on SNL. He was the first musical guest of SNL's 50th season recently. And I caught him in this incredible moment. We got to got together in a hotel room in New York City. I'm surprised he even had an hour to spend with me. He's so busy between

everything he's doing and the tour he's on. The album he has coming out beautifully broken. So I caught him in this moment where he had just played a sold-out show in Boston at the arena where the Celtics play. Then he had sold out the next night, Madison Square Garden in New York. Next day, he headlines the Global Citizen Festival in Central Park in New York, tens of thousands of people in the park watching him. And then that same night he does SNL. Next night he sells out the Prudential Center in Newark, New Jersey, across the river. Then he does Fallon and then goes back out on his tour. So it was just great to sit with him and just let him kind of take a deep breath and appreciate all that's happened for him.

Just honestly, in the last couple of years when he has exploded. A very troubled youth that he's very open about. Most of his music, in fact, is about it. You'll hear him talk about it. Went to jail for the first time at 14, at age 16. He was charged with aggravated robbery as an adult, a charge that has stuck with him all these years. He's 39 years old now, about to be 40. Still can't vote.

He's getting turned down when he wants to live in certain areas and communities to buy a house, having trouble with insurance, can't own a gun, all the things that come with something that happened when he was 16. But, man, he owns up to it. Makes no excuses. Says, I'm not a victim. I was a bad kid. I was a bad young man. but his story is about redemption and hope.

And now trying to sort of be a symbol of all that for other people who may find themselves in similar circumstances. So I will step out of the way and let you listen to really, this is one of my favorite interviews just because of all he's been through and where he is now, how grateful he is and how he's turning it into helping others. So sit back, relax, and enjoy Jelly Roll right now on the Sunday Sit Down podcast. Jelly, so good to meet you, man. Honored.

Thanks for doing this. Thank you. Honestly, I'm just happy we've got you to sit still for a few minutes here, as busy as you've been lately. Even while you're here in New York, selling out Madison Square Garden, playing Central Park for the Global Citizen Festival, then hopping downtown and doing SNL. Oh, yes. You did Fallon. You did Boston before that. New Jersey Sunday.

Jersey Sunday. And as we sit here, you are a handful of hours away from another show in Western Pennsylvania. Yes, sir. What has this weekend been like for you? Nothing short of unreal. I would say I dreamed about it, but that'd be a lie. I wasn't brave enough to dream this big. I love when people were like, this was my dream country.

I'm like, how cocky were you to feature? You know, it's like, that's crowd, how brave? So for me, it's like just experiencing it. Being present's been the best part, too. I also had a real understanding of how country I am. All my New York friends have been making fun of me because when I went to Central Park, I was like, dude, this is from home alone,

and this is where Garth Perks played the infamous Central Park show, and they're like, that's what you know Central Park for. And I was like, yeah, and I'm excited to go. That's fair. Both of those things happened there. I thought they were really cool, you know, big moments. But Saturday Night Live is something you watch and just, I mean, what a, you know, one of the greatest shows, I think, ever.

I mean, and the idea of it just, and I watched some of my favorite performances ever on Saturday Night Live, like when my favorite artists made their debuts, I remember how important, like I felt special for them, you know? And I just hope that registered to my people, too, of like how big that moment was for all of us, really, especially, like, who I represent

and the slice of America that I speak for, we're often don't get a chance or we're often not spoken for on platforms as big as Saturday Night Live or Willie Geist. So this is a big deal for us, man. Well, we're thrilled to be sitting with you. I've heard other artists say there's their career before SNL and their career after

SNL, only because not that you're doing anything different, but an entire new world opens its eyes to you. Did it feel in the moment like something was happened? Did it feel like a moment? It felt like a moment when it was happening and all night, and I have a rule now that whenever

we have really big things happen in our life, I completely disconnect from anything outside of what's happening in it. So I didn't even poke my head up out of my turtle shell till yesterday to go, did everybody else think it was as cool as I felt like it was? You know what I mean? And it's been really overwhelming the response. That's probably smart, right? Just enjoy it. Don't worry about what other people

are saying about it. Exactly. Because when I, because I left there feeling like, man, I could be wrong, but I feel like we just had a really special moment, you know? I'm in Saturday Night Live, a sketch comedy place, you know, everybody's laughing and I'm singing a song and I'm watching this crowd cry. I'm watching emotional tears happen. I'm like, this is happening in the middle of a funny show. Yeah, right. I wonder how this is going to connect with people outside. It did, man. It did.

And by the way, you were great in the sketch you appeared in. That was my favorite fun. I was a comedian all of a sudden. I was willing to sacrifice a song to be in a sketch, by the way. My published was so mad at me. I was like, we'll give up a song if we have to. If they're shut on time or something. And she was like, we're not going to give a song, man.

I was that excited to do a sketch. So to me, that's like the ultimate. Anytime I got to see one of the artists do a sketch, it was like, I don't know what it was. It just felt special and rare. And I just was so excited. I was pushing for it all week. You were great. You were really great.

People still talking about it. And I was looking, this weekend is sort of a microcosm of what's been happening in your life. It feels like for the last couple of years, even just looking at your tour schedule, I'm looking for days off. And they're few and far between. Have you had a chance in these last couple of years to stop and appreciate it? Or are you just going 100 miles an hour? No, no, no. We stop.

We stop and regroup and settle in. And one way to appreciate it is I'm pretty much fun. phone-free. I live a pretty phone-free life these days. So that's a great way to be present. And my touring schedule, believe it or not, is the way I prefer to tour. You know, I came up old school in the van. There's a lot of artists out there, and I'm not talking crap, but they didn't have to, because of the internet, they didn't have to cut their teeth in a bar. So, you know, we're a little bit older, but it happened a little later for me in life. So I still had to actually get in a van and sleep in a van and do $50 shows with chicken wire around the stage, you know,

in case somebody tried to throw a beer at you. Like Blues Brothers. Yeah, We live Blues Brothers. So we were so used to doing five shows a week anyways because, you know, when you're getting $50 a night, any night you're not playing, you can't afford to put gas in the van. You know, you can't afford to pack of cigarettes gas or a hotel, you know?

You got to pick one. You're either going to buy weed or gas. You know what I'm going to eat? You got to alternate nights on that? Yeah, it's a different thing. It's like, oh, we're going to be sober, but we're going to get there. You've got to manage the budget, right?

You live that way for so long that when it's time to keep doing it, you're like, well, this is the way we like to do it, though. It's the rush. I also believe that it's a tour starts to become a machine. Like, you start to fill a flow with the guys. When you do it every weekend, like most of my country peers, they come out and they're having to re-reve the engine every week. I mean, we're rolling, dude. Even when it's time to sing, it's, I'm singing with Kelly Clarkson yesterday, and normally I would have been, I was still nervous, but normally I would have been just knee-knocking nervous. But we're singing one of my songs that I've sung 30 times in the last 43 days. You know what I mean? She's like, I am primed to sing

this puppy right now. What is it like having played for $50 with chicken wire around the stage to walk out at Madison Square Garden and see that famous ceiling and see the place sold out and to know where you've come since those $50 gigs? Man, it's so, it's overwhelming. And I'm already kind of an emotional guy. I didn't cry much at all until I was in my early 30s. No, I just can't stop. You know, it's like, it's like it was almost like when you drink too many beers and you pee the first time and then you just keep going all night. That's been my relationship with the emotions. And you walk out, but the first time I walk into the arena, just empty arena, you look up and you're just like, I was emotional before there was a soul in the building. And then you sell it out

with souls, you know, and I'm big on telling people that this isn't a ticket stub. This is a story. There's a story. They ended up here. There's a story that brought you to a jelly roll show. You didn't stumble by MSG and go, I wonder what's happening there tonight, you know? So I was emotional before the souls were in there. Once you put the souls in there, man, I mean, it was really overwhelming. So you're singing some of the new songs off the new album, beautifully broken, which is going to be a massive hit. I got a chance. Thank you to listen ahead of time some of the songs. It's incredible. What did you want to say with this album that I know took you some time because you want to get it right. What's the message of this album, if there is one?

Redemption and Hope is where it all leads to. But I feel like my last album was called Witsitt Chaplin. I named it after my childhood church. And it was kind of my letter to my faith. It's kind of how I looked at that album. And I look at this as more of a diary into my mental health. And it's very vulnerable and honest. And I was hoping. to create a community with it as well. I want people to, one of the coolest things that's ever happened to me is when I went to the Grammys this year was right after I'd spoke at Congress about the fentanyl crisis. And I won't name their names, but A-list celebrities. I mean, the biggest celebrities on earth stopping me on the red carpet and going, I have a son, I have a cousin.

Yep. I have a niece. I have a friend. This did this, this, you thank you for this. How can I help? more, even cooler, how many of them were immediately called to action with me? You know what I mean? And I was like, man, I really am speaking for a group of people that have never been spoken for. I'm really putting a light on extremely dark issues. And I take extreme pride in that too. So beautifully broken means what exactly to you? That we're all broken, but we're beautiful. You know, I think we're all a little broken inside. And I think if we were more honest and vulnerable about where we're broken and how we feel about things, and it could create more conversations to grow and move forward. And I think that that first step is going, just because one's broken doesn't mean they're not

beautiful, you know? We're in a world full of only seeing the highlight reels of everything, right? It's like, I think it's okay to show a blemish every now and then and kind of humanize everything. We're not humanizing each other no more, man. It's sad. We've kind of lost a sense of humanity a little bit. And I think just kind of stepping forward and accepting that we're broken is the beginning of that, because we're all just a little up.

Yeah. You know? Yeah. I think... I could not find a better word. No. I was like, I don't know. You're good.

You're good. I think that's why people have been so drawn to you. One of the many reasons, in addition to the music, is that you kind of transcend all the crap we see on TV, which is us versus them, the politics, the bicketts, the big. the fighting, like you said, this sort of sanitized version of people we see on Instagram. Is that a conscious thing for you to say, I'm not going to participate in that? I'm going to be real over here and work on real problems, and you all can do that. But I'm going to, I'm going to fix some things, hopefully. Yeah, I just, I come from a kind of roll your sleeves up and do it place,

you know, don't talk about it as much as you can do it. Kind of put feet on your faith. It's kind of a big place for me. And it's also like, I just stay out of stuff that I don't know. know anything about neither. And man, I just, I kind of wish a lot of people would take that approach too, because a lot of people that don't know a lot that are talking a lot about stuff they don't know a lot about. And I just don't want to be one of those guys. And I know what I know and I know what I'm here for. I know what God's plan for me is. I feel like I'm kind of living directly in what, because I know when I wasn't living this way, nothing was going right. And I know ever since I've been living this way, man, I mean, the walls have fell down in my favor.

It is crazy. He has parted the sea for me. It has been. been unreal, so I'm just going to keep focusing on what I can help. Plus, I'll tell you something my daddy told me. Change starts in your heart, and then it starts in your house, and then it starts on your street, and then your neighborhood, and then your city, and then hopefully your state, and then maybe one day your region, and it grows out, and maybe one day will change the world, but all of us, it has to start changing our heart and our house, you know, and I think I'm just getting to my community now. So maybe I'll venture into being more broad about things later and have more of an opinion on national things, but I'm still the kid that just recently changed my heart in my house.

Yeah. You know what I mean? Yeah, right. Just starting to kind of slowly venture out into the world with my message. I mean, a lot of people change their heart, but then they don't take that next step to the community. And you really, really have done that from the jump. I mean, this has been an important part of your life, which is to say, I've got this platform now. I've had this success.

What can I do with it? And, man, have you done a lot with it? why is that so important to make that such a centerpiece of your music and your message, the things that happen off the stage? I think being, I mean, full disclosure, just being the problem, knowing and identifying that I truly was the problem, like it was so hard to look in the mirror and go, man, you were wrong. Your approach was wrong because I had a victim mentality forever.

You know what I mean? It was everybody's fault but mine. It was all the circumstances. but me. And it started with me just having extreme accountability and going, man, I helped make this mess. And then as my heart started getting right and getting more pure, I started feeling a responsibility to go clean it up. You know, there's kind of this old saying that you clean up after yourself. I had left a lot of stuff that I needed to go back and clean up. You know, I've been carrying a big broom around the last few years, and I still have a lot of work to do. Well, you're

cleaning up your own stuff, but in the process, you're helping an awful lot of other people. I actually just heard a short while ago about this project you're working on. with Judge Dinkins, I think his name is, right, to a guy who you obviously interacted with when you were young. Can you say more about that project? Yeah, it's actually, so Jim Todd was the district attorney in the Davidson County Juvenile Courts whenever I was a juvenile. And I had a charge whenever I was younger

that I was charged as an adult because the crime was that heinous. I was 16 years old when I committed the crime and I was charged as an adult. Jim Todd was the prosecuting attorney that was petitioning to bow me over at the court. Judge Dinkins was a judge in the juvenile court. Now fast forward 25, 30 years through, I guess God, it's been that long. Fast forward 25 years, Jim Todd is now a judge. He's no longer a district attorney.

And Mr. Dinkins has passed away, God rest of soul. and Jim Todd's dream was to come back now in the name of Judge Dinkins and bring opportunities to at-risk youth and for kids coming out of juvenile and to create vocational work for them, ways to get your GED, because I was a product. I didn't get my GED until I was 24 in adult jail. You know, he literally is making it a point to go back and start knocking and fixing everything that he thought wasn't right with the system that he was

actually prosecuting for. And that just, to me, says wonders about who he is. So when he called and said, I have this idea to do this Dinkin's house, and this is what we're going to do, I said, I'm all in. I'll row, I will hang drywall and cut a check. You tell me which one you need me to do, if not both, you know? So I jump straight in. So you've cut them a check.

You've cut all kinds of other checks. You're given a portion of the pre-orders to this new album, to places that are important to you. you really, it seems to me, you walk the walk. This is something that you were invested in, all in. Yeah, I'm all about it, man. I feel like I didn't want to be one of those artists that just talked about money and raised it.

I wanted to give it away. And I think artists, respectfully, I just, you know, you watch, my dad used to tell me a smart man to learn from his mistakes, a wise man to learn from the mistakes of others. And I got to watch a lot of people do it right and gain wisdom and watch a few people go, have I ever had the opportunity,

I'd probably try it this way. And it was just important to me to get back. So you're talking about your dad a little bit. We're talking about being beautifully broken, which takes me back to Antioch. Oh, yeah. In your younger years, people don't know,

kind of out by the airport there in Nashville. What were those early years of your childhood like? What were you feeling? What were you going through that led you to that first path that you've taken yourself off now? Well, I'm from Antioch, and Antioch is a really unique place.

But what I've learned about that's what's so unique about Antioch is there's one everywhere all across the world, you know? But it's somewhere between middle, lower class and middle upper class, depending on what side of the tracks you end up on. And my father was a really hardworking blue-collar man. He ran a meat business that he got from his father. It was a family-owned business, a D-Ford business. My mother was a woman who fought extreme anxiety and depression, and because of that, she struggled with drugs at times. She was very reclusive because of the nature of her mental health. And my relationship with music kind of came through her because when she would come downstairs,

it would be for music. She'd come downstairs and cook us dinner and play songs. And like, it was just, I always used the expression. I would watch my house go from kind of dreary to a nightclub. And as a child, I just immediately related to music, help people. I was like, oh, and I realized that there's a lot of people that walk through life and music's a beat. It's a rhythm.

It's a... But for me, it's a... But for me, it was something magical. There was medicine. There was something that happened when she turned a record player on, that the whole house changed. Neighbors started coming over. And she wasn't just playing the Bee Gees.

You know what I'm saying? It wasn't like we were just staying alive. I mean, she was playing some dark stuff, too, and people was just attracted to it. And she'd tell these great stories. It was cool. And that sort of taught you instinctively, intuitively, music helps people.

And did that then lead to your own interest in performing music? Was that about helping your mom in some way? I think so. I think that it was a way to connect with her too. And I wasn't always articulate, so I would write and I would present things kind of that way to the family at times

because I just couldn't really figure out a way to get my word. So I knew that music was a way of connecting with her. And I think that I was, to this day, I still think I'm writing songs to help her heal. But I think that it also made me the writer I am because I started writing as such a young age. But you started writing hip hop, right? I mean, which I was...

I had no clue. We learned that later. So I grew up in New Jersey, but went to school in Nashville. And so I would always explain to people, hip hop and country music actually aren't that different, right? They're telling the stories about what's happened outside their front doors. The instrument's different. The way they phrase it is different. but it's the same storytelling.

It's just very different places. So how did you come to hip hop as your first art form growing up in Antioch? Ooh. I mean, it was the 90s, I think, and I was going through the same thing. Hip hop was everywhere. It was exploding through the world. And our neighborhood was no different. Another thing about Antioch that I'm proud I came from is it's very, very, very diverse.

And I know everybody claims to be from a diverse. diverse place. But Antioch is truly, if you've ever been to Antioch, it's a very, very, very diverse place. So we had so much culture on our street anyways. You know what I mean? We had so many, we had black families, Iranian families, just regular white trash families, you know what I mean, Mexican family. We had all these people and it just felt like the language of that community was hip hop in the 90s. Like no matter what house I went into, even if it wasn't their first language, this is what they were playing. And we were just blown away by it.

And we immediately wanted it in. I went to a school called Cameron Middle School that was right across the street from J.C. Napier Projects. And I'll never forget, I walked in the first day and right outside the lunchroom they were beating on the table.

And my brother had told me before I went to school, he was like, you better learn how to rap or fight or something. You know, that's a rough school. So I went in there and I came in. I was like, I seen them rapping. I was like, I'm going to try it tomorrow.

And I walked up to the table the next day and I tried it. And I said one thing that was kind of halfway cool and I got a pop. And that was it. Off to the races, man. I was writing every day. That was your first audience. That was my first audience. And they liked what they heard.

Yeah, because I remember you would walk up to the table back then and they'd be beating with pens and pencils. And me and MGK just recreated that kind of scene on Jimmy Kimmel. I saw that with Travis. Yeah. But they'd be beating on the table. And we would walk over. And then you would kind of get in, like, you would go through the measures, right? And somebody would kind of come out and you'd be like, yo, yo,

yo, and that's how you'd come in. Yeah. And then you come in, I think I said two things. But it's like, because I was a white kid trying, I don't think I said anything cool. They were just like, this is crazy. This is awesome. So the next day when I came and I felt like a superstar. Yeah.

Everybody was like, he's the white kid that rats. Because, you know, back now, you could throw a rock out this window and hit a kid that'll rap for you. That's true. Right now. You know, back then, a white kid rapping? Absolutely not. On that note, you made me think the fact that Eminem sampled your song on his new album, that's got to blow your mind as the kid who was in that cafeteria kind of doing a version of Eminem.

You want to have a funniest story about this? Yeah. First of all, lifelong Eminem fan. Yeah. The coolest call I could have got. And they send me a link to listen to it, like, a week before, two weeks, three weeks where the album comes out. They go, hey, we're just sending this over for approval. I'm like, oh, this is it.

So I'm listening on the couch, and I'm like, it's vintage. It's like Eminem show Eminem. He's like, so just a real story. And it's, I immediately put together. Even though I don't know the theme of the album yet, I'm like, this is if he didn't get sober. Like, he's writing this as a letter to his family if he didn't, like, had things not, had he not got sober.

So I'm like emotional. So I call the whole family and like, y'all have got to hear this. I've got the M&M song. And I go to hit play and the link disappeared. It was the one list. Link, I didn't know. I mean, he is the most famous artist ever.

So you get one shot at it. The best part was, the whole family's in there, and they're like, are you sure they sent it to you? I'm like, I promise I'm going to be on his album. And even my daughter's like, okay, dad. He kind of walks off. She's 16. I was like, oh.

That's just another pinch me moment along the line. I have to believe. That's incredible. It was cool. Hey, guys, thanks for listening to the Sunday Sit Down podcast. Stick around to hear more from Jelly Roll right after the break. Welcome back now more of my conversation with Jelly Roll. So you're getting your feeling music a little bit, hip hop, you're doing your thing in Antioch, and then you get tripped up, right?

And you're 14 and you're 16, you're finding yourself in trouble, starting to go to jail. What was it like to be a juvenile, a young man already in the prison system? And did you see any hope on the other side of that as a teenager? I didn't see. That's kind of why I'm such a big advocate, too, for juveniles and the Dinkin House, and what we do with our working juvenile now is there wasn't a lot of hope for kids in there. There wasn't a lot of programming. Even the idea of the place was institution, gray walls, concrete bunks,

I mean, steel bunks, concrete walls, steel commode, steel desk, real, you know, 1960s prison style was the whole facility. They still haven't, they still didn't paint the walls for 20 years, except for the same color. You know, I mean, it's just a really dark, dreary place. Nobody ever came through with much hope. Nobody ever said much to us. And listen, we were criminals. I mean, we were the worst of the worst that the state had the offer.

I want to be very honest with that about people. But we were kids. And I understand that now more than I used to, because it took me a long time to forgive myself for what I did back then. but now I have a 16-year-old. And I'm going to tell you something. There are some days this kid, I think she's got the brilliance of a 40-year-old.

She's got the spirit of a 60-year-old woman. And then there are days where I'm like, you're 12. You're still 12 years old even though you're 16. She is such a child. She has so much growing and developing to do. I could never hold anything she did right now against her the rest of her life. You know, if nothing she could do right now

that I would hold against her the rest of her, her life because I know she's not thinking properly. But I felt like we wasn't really treated that way. And I'm not playing a victim here. I'm just, you know, we were kids, man. When you look back and reconcile with your past trauma, look back at your life, you go, that's what it took for me to forgive myself, because I knew I was making bad decisions, you know? But when I was a child, I did childish things. It's funny you mentioned your daughter, because it seems like that was the turning point for you where you didn't see that hope. And she's born while you're still locked up and something changes in your mind. Is that right?

That's it, man. It was, I'm a kind of old-school Southern man, so I always reference a Bible scripture about this guy named Saul that was walking down the Damascus Road. And God kind of revealed himself to him, and it's kind of all that took it just right then. He went from being like, he was a guy that was killing people that believed in God to being like, I'm all about God. And I literally call it my Damascus Road experience. That's what happened that day. And I knew the woman was pregnant and still wasn't real to me, you know. But as soon as she was born, sitting in a jail cell, having $17 of honey buns and potato chips to my name. I owned one outfit, the one that was in the jail.

I didn't have a car. Here I am responsible for a child. I mean, I was the lowest common denominator in life. You know, I mean, I was scum of the earth. I was a crack dealer. I was a horrible, horrible human. And I was like, I can't do this, man. I can't be a horrible.

I got, you know, I got to figure this out. So you get out. I think you finally get to see her on her second birthday. Is that right? So when you're out, you see your daughter. You're at her birthday party. What's the plan? How are you going to take care of her?

Is music going to get you there? Or what are you thinking at that point? Well, I only had one skill set and it was music. So I was like, for me it was music or bust a little bit. I immediately, this thing had kind of relatively new to the scene at the time, was called YouTube. You would go on your desktop computer and type in YouTube.com. And a friend of mine had bought a, his name's Chad Arms, he bought a flip cam from despot before I got out of the day. I got a camera we can play with.

So we just started recording music, screaming into that camera, uploading it on YouTube and selling t-shirts out of our car. We would sit outside of the bars on Dummbron Street or abroad. I'm just sold $10, $15 shirts. Have you ever been down here in Manhattan and somebody hand you a CD in like, Oh, yeah. I was that guy. Oh, yeah. Oh, yeah.

Oh, yeah. It's not until it's in your hand that they ask for the money. That's the trick. And make sure you take it first. That's it. That's it. Salesman number one, I give you the product. Now, you have to convince me to take it back.

I've learned that the hard way, walking up 6th Avenue. It's easier just to give me five bucks, man. I'm telling you. I got a lot of bad demos in my bag. Yeah. It's a true story. And then I learned that you can sell a bunch of CDs and nobody still listen to your music. Right, right, right, I have to take a new approach.

Right, exactly. So that, I mean, you're good, right? You've got good flow and you find some success, but. I'm not terrible. I'm just bad. I was too generous, maybe. Very nice. Thank you.

So at what point does it go to the next level where you're like, all right, here, I can make a career out of this. This seems to be going in a direction that maybe this is my life, music. Yeah. My dream scenario coming out of jail was I read a double XL magazine with a guy named Tech9 and Travis O. Gwynn in it. And they were independent rap. He was an independent rapper in Kansas City. And they were printing their own T-shirts and they were shooting their own music videos and doing their own tours. They were completely independent.

And to me, if I got halfway where he was, I would be set. So I started kind of studying their model. And I started putting out mixtapes and really focusing more on the music, less on the product I was selling. Because the hustler in me was just trying to sell product, not make good product. And then, like anything else in life, you spend 10,000 hours under the grind of it. You start to get better at it, start developing it. And I had just got to the point that I was selling a couple of thousand tickets pretty much everywhere from the rust belt down. And you could kind of feel the impact.

And I've probably never told this story this way. But at that moment, me and my wife thought we had made it. I mean, we were living in a nice neighborhood. We were selling a couple thousand tickets a weekend. I mean, life was great. My daughter was in the school district. I always dreamed I could have been in. You know, I mean, it was just, everything was great.

I was, to me, I was on the, I was on top of the, I was, I had played Saturday night live then, you know, I was on Saturday night. Made it. Made it. And I dropped a song called Save Me. Yep. And, man, I'm a big Malcolm Gladwell fan. You ever heard this guy?

Oh, yeah. Oh, yeah. That's your 10,000 hours guy, yeah. I had read Tipping Point. probably five times in jail. And I can surely tell you that I would always watch and go, I wonder if I'll ever have that tipping point. And I can truly say that for me, save me was it.

Save me was the beginning. Now it was a long wave down, but save me was the beginning of the tide turning, where it was like, oh no, like we went into the pandemic selling 2,000 tickets. Our first show out of it was 7,500. in Georgia. Wow. Wow. Just saved me that fast.

Because you dropped that May, June of 2020, something like that. They were still spraying boxes with Lysol. Yeah, yeah. And it was not just a change for you in the level of success you started to enjoy, but musically it was a change because you were singing. And somebody saw that in you, right, in a way that you hadn't seen before. Yeah. The first comment under the YouTube video says, it's me.

I comment first, of course, and I'm like, Hey guys, I wish I'm paraphrased, but it's like, hey guys, a little different for me. Let me know if I should put it on the album. And I was telling somebody, I didn't write that like, you know, like arrogant, like, should I release this? You know, like, no, like, it was more like, I just want y'all to know. I know this is different. If you don't like it, that's fine. And if you do like it, I'll put it on the album.

It's your choice. I was literally just open for, you know what I'm saying? And I knew that I had told my story on there, and I just felt so. I felt so convicted about that song that I recorded it on a Sunday, shot the live performance of it then, edited it that Monday, and put it up Tuesday morning. I mean, I was that convicted about the song. The original YouTube version of it, to this day, that says unreleased, is the demo version of the song. We never changed the sound out for the actual version. And your gut was right. It was, it transcended hip hop, it moved into this different space. And now you've got people in Nashville saying, oh, that's a country song.

And he's a country artist. How did that sit with you? Did that sound good to be in the world of country moving over from hip hop? Well, it felt good because they were already calling me a country rapper because I was, by nature of dialect, I'm hard to hide. How I sound, you know. But so I think for me, it was telling the same story just in a different way. Yeah. I feel like I've been consistently telling kind of the same story.

My buddy Ernest has the best analogy about me, and I give him credit because he just did it great. He said, you've always been in the same living room. You've just changed the furniture. And to me, that was the greatest analogy of what happened to Jelly Roll. I was always in the right place. I just had the wrong furniture. Yeah. Right.

Your soul and your message and all those things stayed the same. It's always in the right place. I just had the wrong furniture. So as things have gone up like this so quickly for you, I'm curious how you've handled it personally. What's it been like to become so well-known, immediately recognizable, your face and your voice and everything else. How are you managing that side of it? Oh, I think I'm doing pretty well. That don't bother me at all.

I feel like, as far as like, I don't feel famous because I'm now Eminem's a friend of mine and he's famous. You know what I mean? I have famous friends. The Rock's a friend of mine. He's famous. It's all relative. It's all relative. I am not famous. But to me, it's just the world's starting to feel more like Antioch. I kind of always got the hey jellies in Antioch when I'd go out. You know what I mean? Because I've been jellies since I was a kid. My mama gave me the nickname. So for me, it's just like, I feel like I'm back home kind of everywhere I go now. Because the cool thing is most people just hey jelly. They'll just be like, what's up jelly? And I just like, what's up y'all? It's really cool. Like, especially the people that do it for me. It touches my soul because I'm walking through 30 Rock, and it's all the union guys. Yeah. Like, that's what I'm here for. You know what I mean? Right. That's it.

So that's all cool. What I'm learning to deal with is the schedule. Yeah. And I'm learning to deal with people. I didn't realize how much of a very isolated life you live until it's, you walk out of your bus, and it's 30 people. You walk out of your hotel room. Right. There's a whole team that are kind of waiting on you.

and I don't handle that pressure well all the time. So I'm doing better with that. But other than that, everything else is really smooth. I may hear I am being too honest again on TV. I'm oversharing. We love it. We love it. That's why people love it.

I'm supposed to be like, it's all going great. No, it's good. But this is beautifully broken, right? We're vulnerable. Being honest, I'm not a, I'm grateful for it and I'm learning. Stick around for more of my conversation with Jelly Roll right after a quick break. Welcome back now to the rest of my conversation with Jelly Roll. The speech you gave when you won Best Do Artist went viral immediately.

I mean, that was a beautiful, that was a Baptist preacher on stage. You went into some other gear speaking to your audience and speaking to anybody who's struggling and needs to get to the other side of it. And you told him to stay there and talked about the windshield and the rear premiere and all that. Was that all spontaneous? And after the fact, did you appreciate how it had taken off and touched so many people, even outside that room? Well, first, well, part one for me is a callback

to something we talked about with Saturday Night Live. I'm really big and big moments of not disconnecting. Okay. So we go straight from there, and me and Lainey Wilson go to our after party because she's one of my best friends. She's like a sister. And me and Lainey are hanging

and all of our country music friends have come to see us. And we're just, I didn't touch my phone until the Thursday night. So the awards were on a Wednesday, right? Thursday night. Because I just asked my wife, and I'm weird about stuff, so I just go, how's it going? She's like, you're going to love it.

That's all she said. I was like, cool. And I just kept moving on. So by the time I grabbed my phone Thursday, I was like, oh, no, this is viral. Yeah. This is unreal, unreal. And then, of course, I woke up the next day to the Grammy nominations. Yeah.

You talk about just another, talking about that. God blesses me with three sometimes. I just have three crazy days in a row. But, yeah, that was, that was one, I said, I was just so disconnected. And two, the actual speech was, if you've ever come to see a Jelly Roll live show, my show is scattered with these kind of moments that are like very, very inspirational or emotional. And it's very fiery because I grew up in a Southern Baptist church. It's just, if you've ever get around me and I get really excited, you've probably already seen in this interview.

I already, I naturally get up. And so it naturally happens. So I think that was just manifesting what happens anyways. Our show is church for people who traditionally don't go to church. Yeah. And then to think, Jelly, that a year later, so that was in some ways a coming out party for people who didn't know everything about you. One year later, now you made the leap where you're nominated for Entertainer of the Year. Is that not crazy?

An album of the year and male artist of the year. I mean, you are in an elite club of country music. What does it mean to you to be on a list with Luke and Stapleton and Lainey and Morgan Wallen and all them? Oh, we're talking about I still don't fully, I'm still dealing with the fact that I don't feel fully fit in there yet. Not as a country guy. I know that they love me in country music, but like I just don't feel like I'm that caliber of artist yet still. When you look at Morgan Wallin or Laney Wilson and Luke, when I looked at the entertainer of the year category and I'm in there, I'm like, these are monsters. You know what I mean?

Like, dude, I am a fly on a bull's butt. You know what I'm saying? This is not even close. The Winston Chapel album one got me, it's probably the one that, the entertainer of the year, I couldn't even cry about it because I was just so blown away

that they would even consider that. The album of the year was emotional for me because, you know, I wrote that album about my childhood church, a church that I didn't go back to for 25 years. And I only went back out of respect to say, hey, I don't legally have to tell you all I'm doing this,

but I want to come look y'all in the eye and tell you that we're, you know, I've decided to use this as a muse for an album I'm doing. And they were like, come in. As far as we're concerned, you're still a member. You never told us you wasn't. They fed me, took me in. I mean, it was just the coolest thing ever.

And the producer from that album and I have known each other for over 20 years. He produced hip-hop beats for me back in the day for 50 bucks. Wow. So that was special. And, of course, the male vocalist. I mean, I'm thinking about Cody Johnson first and foremost. I don't know if you've ever heard Cody Johnson sing. Oh, yeah.

It is, he has, there's a Bible scripture that says the Lord's voices of a thousand running rivers. And the Lord's voice is a thousand. Cody's got a hundred. You know what I mean? I mean, it's that close, you know. So just being considered, the CMAs too is the biggest night in country music. You know that. So just to be involved, to be considered, to be back.

And the only thing I'm sad about that night is that as of that night, I'll no longer be the new artist. That's right. It will be crowned to a new king or queen. And I hope they're as excited about it as I was. Well, which gets us back to the album to Beautifully Broken, which is, with Witsitt, it was almost an introduction, right? Oh, who is this guy? Oh, he's so interesting. His sound is cool.

He looks cool. And now people know you. Right. And so here's my next effort. Does that feel different this time around to you? You've established yourself. And now here's my follow-up to the thing that you fell in love with first, maybe. Yeah.

And it's nervous because you're... This is my stay moment. Yeah. Right? You know, this is the, it's funny, I put out 300 songs, but I'm actually going to drop my sophomore album. Right. You know what I mean?

I'm on my second album. Morgan Wallen told me that. And it changed my perspective one night. He said, I was like, I was leaving the stadium and I was like, man, this is beautiful. He said, you'll be here soon. I don't know if I'll ever get the stadiums, Bubby. He said, you're selling out arenas if you only dropped one album.

And I was like, and he stopped. He said, I know you put out 300 songs. He said, but to the world, you dropped one hour. album. So then that, but after that I was excited. I was like, you're right. Then I got in my car. I was like, oh no, the sophomore jinx. And I text him like, thanks for ruining my week. You know what I mean? But I hope that this album is to prove that I'm here to stay. And it was most important to me to double down on my message here. I feel like people are watching and they care what I have to say. And I think it's important that when that happens, you double down on

who you are. That's why doing winning streak at Saturday Night Live was important. I love that song. That's why that was important for us to make sure that no matter what audience we're in front of, we're going to be us. Yeah. And the winning streak for people who haven't heard it or are about to hear it when they listen to the album, that's a scene that you've captured from a place where you've been and so many people in this country have been before. And you wanted to share that through a song. I just witnessing something so transformative happened in person. And you think to yourself, man, if the rest of the world could see this, the compassion, the humanity, you know, just the compassion that would be showed.

And I think that's our responsibility of songwriters, too, sometimes is to tell the stories that aren't being told. That's what my favorite songwriters were doing. That's what Waylon was doing. That's what Willie was doing. That's what Merle was doing. It's what Jim Crocey was doing. It's what James Taylor was doing. It's what Bob Seeger was doing.

You know, these dudes were just writing songs about people that wasn't having songs written about them. And I wanted to follow in their footsteps. Does that ever feel like a big responsibility? Because you are speaking for so many people in this country, in this world now, that feel like they don't see themselves in popular culture and music or movies. And you have become that voice for them. Have you accepted that kind of responsibility? Oh, a smile.

I can't help but smile because I hope that's the way they see it. I hope that when my people see me in a commercial or sitting on this couch, they're like, that's our guy. Yeah. That's our, so we're on that couch. Like, we're being heard. And, uh, nah, man, I don't, I don't feel pressure. I feel, uh, I feel a great amount of gratitude.

And it's a privilege to have the platform and do it, right? Yeah, man. It's, it's been a long road. You build it and then you get to stand and tell people your story. And it's funny that your story, this started by me. just writing what I was feeling. And then to see so many people connected to the feelings. And then for the first time in my life,

I had something I never had before was purpose. So I kind of thrive off of it now. Now I'm to a point, I'm not writing my story no more. I'm writing, I might have wrote it from the first person, but I'm writing the story of that man that was in that seat for Winning Street. But I write for first person so whoever that person is can identify it as a first person. But to me, that's the way I'm trying to write. I'm telling their stories.

Now I'm like a comedian looking for a muse. Every time I hear one, I'm taking note. I'm making notes in my phone when I meet people at gas stations. I've got to let you go because, like I said, you got a show in a couple hours here. You should have came. We should have set this whole thing up where I kidnapped you and we went to do this show together. Is it too late?

Can we make this happen? We can do that. I'm free. I'm available. I'd love to have it. But I do want to ask you, I was reading a different interview you did where you said, if this album goes well and we fully believe it will

because it's beautiful, it takes you a few more years and then maybe there's some other way, I think the way you put it, that God uses you in this world. Does that mean you take a break from music or you come back to it later or what did you mean by that?

I just, I'm here to tell stories and I'm just not sure what way I'll be telling stories next year. You know? And I do know that I feel led more than I've ever felt lead right now, and I'm just going to keep following, man. I feel like it's going great for me. And I'm definitely going to take some time to spend with the family at the top of the year, too.

Spend a spend with my wife and take my daughter somewhere. There you go. We got a lot of people rooting for you. You deserve all the success you've had and you've inspired so many people. It's a pleasure to talk to you, man. Thank for your time. Appreciate your guys. This has been awesome.

Thank you. Seriously, brother. This is a big deal. Thank you. Thank you, man. Jellie and I left our microphones on as we took a little walk up to the roof of the hotel, where we had our conversation. looking out of the skyline in New York City

a great time for him to reflect on this moment in his career. This felt appropriate, considering you've kind of taken over this city for the last week, looking out at your town. Oh, this is crazy. From Antioch to the top of the Big Apple.

Not bad, huh? I just never would have predicted that anybody in New York City would ever know me, more or less that I would be hearing people would, I don't know. It's just unreal, man. This is wild.

This is it. It don't get no bigger in New York. City, man. This is it, man. And you just dominated it for about a week. And you realize, I look at Nashville because it's a growing town now, because when you went there 30 years ago, you see what's happening. It's on a little bit.

Totally different place. But then you look here and you're like, oh, you know, we're still tiny. I'm complaining about the traffic and it's no problem at all. I'll tell you, Nashville's on its way, though. Yeah, so the 30 Rock is right through there. Yeah. The gardens right down there. Oh.

I'm trying to think of everywhere else you dominated. I got goosebumps. We're in Central Park. Central Park's right up there. You did that, too. We did Jersey. We did Newark. You touched all the bases.

We did. Out of my show, I did 56 arenas on this tour, and five of my shows were in the state of New York. Wow. Or connecting market like Newark. Right, right. So UBS, Madison Square, MVP in Albany, and Buffalo. Right. And if you count Newark, it was five of them up here, man.

That's crazy. You know what's funny is, I haven't done. told this story. My last show in New York City, previous this show, was the little room downstairs at Webster's Hall. Oh, is that right? So imagine that. I have not played a New York City show, except for what I played one of my whole career. I opened up for Yellow Wolf at the Brooklyn Bowl in 2017, and then Madison Square Garden with my next show. How many people do you figure at Webster Hall that night? Crazy? 18, 19, 20? It only held 100. And I could. see all 17 of them.

From 18? I knew five of them personally. I knew five of them that were friends that I texted. I'm in your city. Come to the show. So without friends and family, you're dabbling with single digits at that point. This is a true story.

Chris Webby, who's now a friend of mine, he was a rapper. He was playing the upstairs room at Webster Hall. And it was sold out. So after my show, I drugged my knuckles and my little tears. And after I got done crying, my little puffy eyes, seen his show and it was sold out a thousand people or whatever that top room holds.

And I was like, if I ever get here. Yeah. If I ever get here. You know, crazy, man. And then you blinked and you're selling out a Madison Square Garden. Next thing you know, you're Madison Square Garden. Looking up and going, Billy Joel's really done this 150 times. I know.

I know. Is that crazy? You have stock in this place yet? That is true. You look up with that banner in the rafters. It'll keep you humble in a big moment, won't it? You'll be having a big moment. You're like, I sold out Madison Square Garden.

And you're like, and Billy Joe did it $1. 50 times. You're like never catching that one. You just said something a minute ago. I hope you don't mind my sharing, which is your most comfortable. I don't know if easiest is the right word, but part of your day is being up on that stage

for 90 minutes, the most natural part of your day. Yeah, man. I always say that I'm a big proponent that I was telling you that you don't pay us for the hour we're on stage. You pay us for the 23 hours. We're not on stage. We'll do that for free, man. I would never charge to sing songs, dude.

If I didn't have a show tonight, me and you would go out, have dinner and find a bar with live music, and if they'd let me grab a microphone, I would sing songs. It's what you do. I'd never charge. It's what I do, baby. I write songs and sing them. I'd never charge for that. And you still have that mentality wherever you are, even if it's the garden that you're just singing in a bar, basically?

I'm just singing in a bar, baby. That's it. I want everybody, at some point in my show, no matter where we are, I want y'all to feel like we're one at a bar having the night of our life. And then at another moment, I want you to feel like we're all sitting. in the Indian style and a living room together, having the most intimate, honest moments you've ever had. Those are my two goals at that show every night.

75,000 or 700, same two goals. Just that the bar has gotten a little bigger. Bars got a little bigger, baby. Congrats on everything, man. This is so much fun. Appreciate it. Thank you for your time. Thank you.

New York City, baby. Look at that. My big thanks again to Jellyroll for a great conversation. His new album, Beautifully Broken, is available now. wherever you stream your music and you can catch him out on tour. Like I said, he plays four or five nights a week.

So odds are he's coming to your town soon. And my thanks to all of you for listening again this week. If you want to hear more of my conversations with our guests every week, be sure to click follow so you never miss an episode. And don't forget to tune in to Sunday today every weekend on NBC to see these interviews with your own two eyes. I'm Willie Geist. We'll see you right back here next week on the Sunday Sit Down

podcast.