Jelly Roll on His Rise from a Troubled Past (October 2024)

Summary

Summary of "Sunday Sitdown with Willie Geist" Episode: Jelly Roll on His Rise from a Troubled Past

Release Date: March 9, 2025

In this compelling episode of NBC's "Sunday Sitdown with Willie Geist," host Willie Geist engages in an in-depth conversation with the multifaceted artist Jelly Roll (real name Jason Deford). The discussion navigates through Jelly Roll's tumultuous past, his transformative journey towards redemption, and his ascension in the music industry from hip-hop to country music. Below is a detailed summary capturing the essence of their conversation, enriched with notable quotes and timestamps.

---

1. Introduction to Jelly Roll's Rise

Willie Geist opens the episode by expressing enthusiasm about his guest, Jelly Roll, highlighting his evolution from a rapper to a prominent figure in country music.

[01:11] Willie Geist: "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."

2. A Glimpse into Jelly Roll's Success

Jelly Roll discusses his recent achievements, including sold-out shows at iconic venues such as Madison Square Garden and his appearance on "Saturday Night Live" (SNL). He reflects on the whirlwind pace of his career and the honor of performing at events like the Global Citizen Festival.

[04:01] Jelly Roll: "Honestly, I'm just happy we got you to sit still for a few minutes here. As busy as you've been lately..."

3. Overcoming a Troubled Youth

The conversation delves into Jelly Roll's challenging past, including his incarceration at a young age and the lasting repercussions of being charged with aggravated robbery as an adult at 16. Despite these hardships, Jelly Roll emphasizes personal accountability and resilience.

[03:28] Jelly Roll: "I was a bad kid."

[03:57] Jelly Roll: "Honestly, I'm just happy we got you to sit still for a few minutes here."

4. The Theme of Redemption and Hope

Jelly Roll articulates his mission to serve as a symbol of redemption and hope for individuals facing similar circumstances. He underscores the importance of owning one's past without succumbing to a victim mentality.

[15:25] Jelly Roll: "I started feeling a responsibility to go clean it up... there's kind of this old saying that you clean up after yourself."

5. Community Engagement and Advocacy

A significant portion of the discussion centers on Jelly Roll's commitment to community service, particularly his collaboration with Judge Jim Todd to support at-risk youth. Jelly Roll shares personal anecdotes about his efforts to give back, demonstrating his dedication to making tangible changes.

[16:26] Jelly Roll: "Jim Todd is now a judge... he is making it a point to go back and start knocking and fixing everything that he thought wasn't right with the system..."

6. Transition from Hip-Hop to Country Music

Jelly Roll narrates his artistic transition from hip-hop to country music, attributing it to his evolving musical expression and storytelling. He draws parallels between the two genres, emphasizing their shared roots in narrative and cultural reflection.

[21:43] Jelly Roll: "Hip hop and country music actually aren't that different. They're telling the stories about what's happening outside their front doors."

7. Impact of "Beautifully Broken" Album

Discussing his latest album, "Beautifully Broken," Jelly Roll explains its personal significance as a diary of his mental health journey. He highlights themes of vulnerability and honesty, aiming to foster a sense of community among listeners.

[11:00] Jelly Roll: "It's very vulnerable and honest, and I was hoping to create a community with it as well."

8. Experiences with Fame and Recognition

Jelly Roll shares his feelings about newfound fame, including his Grammy nominations and recognition within the country music elite. He remains humble, acknowledging the support from established artists and the responsibility that comes with his platform.

[43:18] Jelly Roll: "I don't feel fully fit in there yet... just telling the same story, just in a different way."

9. Personal Reflections and Future Endeavors

In the latter part of the conversation, Jelly Roll reflects on his past performances in small venues juxtaposed with his current large-scale successes. He expresses gratitude for his journey and outlines his intentions to continue evolving as an artist while maintaining his authentic voice.

[47:59] Jelly Roll: "I am telling their story. I'm telling their story."

[50:09] Jelly Roll: "I'm here to tell stories, and I'm just not sure what way I'll be telling stories next year..."

10. Closing Thoughts and Mutual Respect

Willie Geist and Jelly Roll conclude their conversation with mutual respect and admiration. They reflect on Jelly Roll's remarkable journey from humble beginnings to national acclaim, underscoring the transformative power of perseverance and authenticity.

[51:52] Jelly Roll: "I was that guy. I was the CD guy in Nashville."

[55:37] Willie Geist: "Week on the Sunday Sit down podcast."

---

Conclusion

This episode of "Sunday Sitdown with Willie Geist" offers an intimate look into Jelly Roll's life, showcasing his resilience in overcoming a troubled past and his dedication to using his platform for positive change. Through heartfelt dialogues and personal anecdotes, Jelly Roll exemplifies the essence of redemption and the impactful role of music in personal and communal healing.

Notable Quotes:

• Jelly Roll on Ownership and Redemption:

  [15:25] "I started feeling a responsibility to go clean it up... there's kind of this old saying that you clean up after yourself."

• On Music as Connection:

  [20:30] "Music was a way to connect with her [his mother]."

• Reflecting on Fame:

  [37:53] "It's all relative. I am not famous, but to me, it's just... the world's starting to feel more like Antioch."

• On Community Responsibility:

  [48:18] "It's a privilege to have the platform and do it right."

---

Note: Advertisements and non-content segments from the transcript were excluded to maintain focus on the meaningful dialogue between Willie Geist and Jelly Roll.

Transcript

[Livegood Representative]

Nutritional supplements are too expensive. At Livegood we're doing it different by making the highest quality supplements and selling them for just a few dollars above cost. From organic super greens and vitamin D to power your immune system to collagen for healthy hair, skin and joints, we offer premium supplements at up to 75% less than other brands. Join the 1.5 million people who who have made Livegood the fastest growing supplement brand in the world. Livegood.comsxm wanna pull off the season's freshest trends?

[DSW Representative]

You just need the right shoes. That's where designer shoe warehouse comes in. Loving wide leg jeans. Pair them with sleek low profile sneakers. Obsessed with the sheer trend? Try it with mesh flats, feeling boho comfy sandals. Nail the whole free spirited thing. Find on trend shoes from the brands love like Birkenstock, Nike, Adidas and more at dsw.

[Willie Geist]

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 Rol. 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 him 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 he's 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. And I caugh this incredible moment we 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.

[Jelly Roll]

With him and just let him kind.

[Willie Geist]

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.

[Jelly Roll]

16.

[Willie Geist]

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. Um, you know, 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.

[Jelly Roll]

I was a bad kid.

[Willie Geist]

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.

[Jelly Roll]

Interviews, just because of all he's been.

[Willie Geist]

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 Roll]

Jelly. So good to meet you, man.

Honored.

[Willie Geist]

Thanks for doing this.

[Jelly Roll]

Thank you.

Honestly, I'm just happy we 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 week, 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. You know, I love when people are like, this was my dream come true. I'm like, how cocky were you to feature? You know, it's like, that's 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 Brooks 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 happen there.

They were really cool, you know, big moments. But Saturday Night Live is something you watch and just, Yeah, 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 important, 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 happening? 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 at 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.

I was a comedian.

All of a sudden, I was willing.

To sacrifice A song to be in a sketch, by the way. My public 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. She was like, we're not gonna give a song away. 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. 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 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. They didn't have to cut their teeth in a bar. So, you know, we're a little bit older. 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 $50 shows with chicken wire around the stage in case somebody tried to throw a beer.

Like Blues Brothers.

Yeah, exactly. We lived Blues Brothers. So we were so used to doing five shows a week anyways. Cause 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 a pack of cigarettes, gas or a hotel, you know, you gotta pick one. You're either gonna buy weed.

You gotta alternate nights on that.

It's a different thing. It's like, oh, we're gonna be sober, but we're gonna get there.

Gotta 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 tour starts to become a machine. Like you start to feel 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 rev the engine every week. I mean, we're rolling, dude. Even when it's time to sing. 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? It'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 till I was in my early 30s. Now 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. The first time I walk into the arena, just empty arena. You look up and. 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 gonna be a massive hit. I got a chance. Thank you. To listen ahead of time to 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 wanted 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. It was called Witsett Chapel, and I named it after my childhood church and it was kind of my letter to My Faith is 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. It was right after I had 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. I have a niece. I have a friend. This did this. This. Thank you for this. How can I help? 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 excuse 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, that 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.

Oh, 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 bickering, 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 go 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 anything about neither. And, man, 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 unreal. So I'm just gonna keep focusing on what I can help. Plus, I'll tell you something my daddy told 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 we'll 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 and my house, you know what I mean? 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, 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 his 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 till 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 Dinkins house and this is what we're gonna do, I Said, I'm all in. I will hang drywall and cut a check. You tell me which one you need me to do, if not both. So I jumped straight in.

So you've cut them a check, you've cut all kinds of other checks. You're giving a portion of the pre orders to this new album to places that are important to you. You really, it seems to me you walked 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 daddy used to tell me, a smart man will learn from his mistakes, a wise man will 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. In your younger years. People don't know 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 hard working, blue collar man. He ran a meat business that he got from his father. It was a family owned business, 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 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 that music helped 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. 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, you know, 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, 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 at such a young age.

But you started writing hip hop, right? I mean, which I was saying, I had no clue. We learned that later, which I. 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 happening 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 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 families. We had all these people in. 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 in. I went to a school called Cameron Middle School. It 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, man, you better learn how to rap or fight or something. You know, that's a rough school. And so I went in there and I came in, I was like, I seen him rapping. I was like, I'm gonna 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.

Yep. 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 Kim.

I saw that traveling.

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 come in. And then you come in. I think it said two things. Ah. But it's like. Cause 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, everybody was like, he's the white kid that raps. Because, you know, back right now, you could throw a rock out this window and hit a kid that'll rap. That's 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 gotta blow your mind as the kid who was in that cafeteria kind of doing a version of Eminem.

You wanna hear the 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 before, three weeks before 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 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 Eminem song and I go to hit play and the link disappeared. It was a one lesson 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, like, are you sure they sent it to you? I'm like, I promise I'm gonna be on this album. And even my daughter's like, okay, dad. It 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.

[Willie Geist]

Hey, guys, thanks for listening to the Sunday sit Down podcast. Stick around to hear more from Jelly Roll right after the break.

[Coop Representative]

We all have that one friend who can fall asleep like anywhere. At the movies, on car rides, or at live sporting events. And I have always been jealous because on the other hand, from noise machines to mo mouth taping, I'm a lost cause. Or at least I thought I was until I decided to make this simple change. Get a new pillow. Coop's original adjustable pillow completely changed my sleep. I used to toss and turn all night, waking up with like, neck pain and feeling drained. Since switching to Coop, I sleep soundly and wake up energized and pain free. No matter if you sleep on your side, your back, or your stomach. You can adjust the pillow's height by adding or taking out the fill. It's a mix of microfiber and memory foam that stays plush and never goes flat. And they offer a 100 night better sleep guarantee. You deserve to wake up feeling refreshed and ache free. It's the perfect time to try coupe with their sleep week sale and get 20 off site wide from March 9th to March 15th. Get 20 off. Visit our website at coopsleepgoods.com health that's co p sleepgoods.com health I've never felt like this before.

[DSW Representative]

It's like you just get me. I feel like My true self with you. Does that, does that sound crazy? And it doesn't hurt that you're gorgeous. Okay, that's it. I'm taking you home with me. I mean, you can't find shoes this good just anywhere. Find a shoe for every you from brands you love like Birkenstock, Nike, Adidas and more at your DSW store or DSW dot com.

[BetterHelp Representative]

This is an ad by BetterHelp. Think about the people who inspire you most. Guess what? They don't have all the answers, but they do know how to ask for support when they need it. Therapy is a great way to find that support. Better Help has experienced therapists ready to help you with challenges ranging from clinical issues to the stress of everyday life. And it's convenient too. Visit betterhelp.com today to get 10% off your first month. That's BetterHelp. H E L p.com welcome back.

[Willie Geist]

Now more of my conversation with Jelly Roll.

[Jelly Roll]

So you're, 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 find 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 work in 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. Yeah, gray walls, concrete bunks, I mean steel bunks, concrete walls, steel commodes, steel desk. Real, you know, 1960s prison style was the whole facility. They still have it. 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 to 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, there's nothing she could do right now that I would hold against her the rest of her life. Cause 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 it 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. Whenever. 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. And 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 gonna take care of her? Is music Gonna 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 bus 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 jail, 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 the Mumbian street or Broadway and just sell $10, $15 shirts. Have you ever been down here in Manhattan and somebody hand you a CD and like, oh, yeah, I was that guy. I was the CD guy in Nashville.

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 because you have ownership. That was salesman. I give you the product. Now you have to convince me to take it back.

[Willie Geist]

I've learned that the hard way.

[Jelly Roll]

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.

It's a true story. And then I learned that you can sell a bunch of CDs and nobody still listens to your music. I take a new approach.

Right, Exactly. 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.

Yeah, you were 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 XXL magazine with a guy named Tech9 and Travis O'Gwin 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 to. And you could kind of feel the impact. And I 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 to me. I was on the. I was on top of the. I had played Saturday Night Live then, you know, I was on Saturday Night Live in my head, and I dropped a song called Saturday Saved Me.

Yeah.

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'd 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. Right.

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 paraphrased, but it's like, hey, guys, a little different from 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 line, like, should I release this? You know, like, yeah, no, like, it was more like, I just want y'all to know I know this is different, and 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 that Monday, and put it up Tuesday morning.

Wow.

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 countryside, 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. It's 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. 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 saved the place.

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'm doing. 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 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. 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. Cause the cool thing is most people just hate Jelly. They'll just be like, what's up, Jelly? And I'll just be like, what's up, y'all? It's really cool. Like, especially the people that do it. For me, it touches my soul. Cause 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? I'm like, that's it. So that's all cool. What I'm learning to deal with is the schedule. And I'm learning to deal with people. I lived a very. 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. Time. So I'm doing better with that. But other than that, everything else is really smooth. I mean, here I am being too honest again on tv over sharing.

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.

[Willie Geist]

Stick around for more of my conversation with Jelly Roll right after a quick break.

[Jelly Roll]

Auto insurance can all seem the same until it comes time to use it. So don't get stuck paying more for less coverage. Switch to USA Auto insurance and you could saving money in no time. Get a quote today, restrictions apply.

[Coop Representative]

We all have that one friend who can fall asleep like anywhere. At the movies, on car rides, or at live sporting events. And I have always been jealous because on the other hand, from noise machines to mouth taping, I'm a lost cause. Or at least I thought I was until I decided to make this simple change. Get a new pillow. Coop's original adjustable pillow completely changed my sleep. I used to toss and turn all night waking like neck pain and feeling drained. Since switching to coupe, I sleep soundly and wake up energized and pain free. No matter if you sleep on your side, your back or your stomach, you can adjust the pillow's height by adding or taking out the fill. It's a mix of microfiber and memory foam that stays plush and never goes flat and they offer a 100 night better sleep guarantee. You deserve to wake up feeling refreshed and ache free. It's the perfect time to try coupe with their sleep week sale and get 20 off site wide from March 9th to March 15th. Get 20 off. Visit our website at coopsleepgoods.com health that's coopsleepgoods.com Health at Designer Shoe Warehouse we believe that shoes are an important part.

[DSW Representative]

Of, well, everything from first steps to first dates, from all nighters to all time personal best.

[Coop Representative]

From building pillow forts to building a.

[DSW Representative]

Life for all the big and small moments that make up your whole world. DSW is there and we've got just the shoes. Find a shoe for every you from brands you love at brag worthy prices at your DSW store or dsw.com welcome.

[Willie Geist]

Back now to the rest of my conversation with Jelly Roll.

[Jelly Roll]

The the speech you gave when you won Best new Artist went viral immediately. I mean that was a beautiful. That was a Baptist preacher on stage. Just 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 them to stay there. And you talked about the windshield and the rear view mirror 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 in big moments of not, not of disconnecting.

Okay.

So we go straight from there. Me and Lainey Wilson go to our after party because she's one of my best friends. She's like a sister. 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 gonna 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. This is unreal. Unreal. And then of course I woke up the next day to the Grammy nominations. We talk about just another talking about God blesses me with three. Sometimes I just have three crazy days in a row. But yeah, that was one is that 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 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?

And 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 Laney and Morgan Wallen and all that?

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 Wallen or Lanie 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 Witch of Ch. 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 y'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. So. 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, 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, there's a Bible scripture that says the Lord's voices of a thousand running rivers. And if the Lord's voice is a thousand, Cody's got 100. You know what I mean? I mean, it's that close, you know, so just being considered the CMA's 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 Witsig. 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. 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 statement 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.

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. He said, you'll be here soon. I was like, I don't know if I'll ever get to stadiums, Bubba. He said, you're selling out arenas. We 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 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 to us.

Love that so 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 happen in person and you think to yourself, man, if the rest of the world could see this, the compassion, the humanity, just the compassion that would be showed. I think that's our responsibility as a 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. That's what Jim Croce was doing. That's what James Taylor was doing. That's what Bob Seger was doing. You know, these dudes were just writing songs about people that wasn't having songs written about battle, 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. Do you. Have you accepted that kind of responsibility?

Oh, I 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. That's our. So we're on that couch like we're being heard and nah, man, I don't feel pressure. I feel a great amount of gratitude.

And it's a privilege to have the platform and do it right. 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 where 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. I write for first person, so whoever that person is can identify it as a first person, you know? But to me, that's the way I'm trying to write now. I'm telling their stor. Now I'm getting. 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.

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 to make this happen? Production.

We can do that.

[Willie Geist]

I'm free. I'm available.

[Jelly Roll]

I'd love to have you.

But I did want to ask you. I was reading a different interview you did where you said. 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 led right now. And I'm just gonna keep following, man. I feel like it's going great for me. And I'm definitely gonna take some time to spend with the family at the top of the year, too. Spend a spin, get with my wife and take my daughter somewhere.

There you go. Well, you 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 you, guys. This has been awesome. Thank you. This is a big deal.

Thank you.

Thank you, man.

[Willie Geist]

Jelly 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 on the skyline in New York City. A great time for him to reflect on this moment in his career.

[Jelly Roll]

This felt appropriate considering you've kind of.

[Willie Geist]

Taken over this city for the last week.

[Jelly Roll]

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. This is it, dude. It don't get no bigger in New York City, man.

This is it, man.

Yeah.

And you just dominated it for about a week.

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 a totally different place.

But then you look here, and you're like, oh, you know, we're still real 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.

[Willie Geist]

So the GAR.

[Jelly Roll]

So 30 Rock is right through there. The Garden's right down there. Oh, I think of everywhere else you dominated. Jersey's right over there.

Central Park.

[Willie Geist]

Central Park's right up there.

[Jelly Roll]

You did that too.

We did. Thursday. We did Newark.

You touched all the bases.

We did. You know, out of my Show, I did 50, 56 arenas on this tour, and five of my shows were in the state of New York 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 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 I played one in my whole career. I opened up for Yellow Wolf at the Brooklyn bowl in 2017, and then Madison Square Garden was my next year.

How many people you figure at Webster hall that night?

18, 19, 20. It only held 100. I could see all 17 of them from 18. I knew 15. 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's 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. After I got done crying, my puffy eyes, I went up there and I seen his show, and it was sold out. A thousand people. Or we have that top Rock Room holds. And I was like, if I ever get here.

Yeah.

If I ever get here, you know.

Yeah. Crazy. And then you blinked and you're selling out.

Next thing you know, you're at Madison Square Garden, looking up and going, billy Joel's really done this 150 times.

I know.

[Willie Geist]

Isn't that crazy?

[Jelly Roll]

You have stock in this place yet.

That is true. You look up that banner in the rafters, wild.

It'll keep you humble in a big moment. Yeah. Yeah. You'll be having a big moment. You're like, I sold out Madison Square Garden. You're like, and Billy Joe did it 150 times. You're like, never catching that one.

You just said something a minute ago. I hope you 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 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 let me grab a microphone, I would sing songs.

It's what you do.

I'd never charge. It's what I do, baby. That's. I write songs. And single, I'd never charge for that.

And you still have that mentality wherever.

[Willie Geist]

You are, even if it's the Garden.

[Jelly Roll]

That you're just singing in a bar. Basically.

Just sing it 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 Indian style in the living room together, having the most intimate, honest moment 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.

Bar has gotten a little bit.

Congrats on everything, man.

Thank you.

So much fun.

Appreciate it. Thank thank you for your time. Thank you, New York City, baby. Look at that.

[Willie Geist]

My big thanks again to Jelly Roll for a great conversation. His new album, beautifully Broken is available now wherever you stream your music. 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.

[Jelly Roll]

We'll see you right back here next.

[Willie Geist]

Week on the Sunday Sit down podcast.

[Coop Representative]

This week only on Meet the Press. As President Trump's tariffs spark economic jitters and the country reacts to federal government cuts, Kristen Welker sits down with Commerce Secretary Howard Lynn and Senator Alyssa Slotkin only on Meet THE Press. Listen to the full episode now. Wherever you get your podcasts.