Like other Chicagoans who left their hometown to become world-famous, both John Prine and Bill Murray remain Chicagoans at heart forever, forever imprinted by the big city where they started their careers in close-proximity to each other. So it made sense to bring these two old friends together to discuss how they went from Chicago boys to legends.

Presented by the Recording Academy Nashville Chapter and moderated by musician/author Peter Cooper, the conversation took place in front of an intimate audience at RCA’s historic Studio A in Nashville. The old friends reminisced about their early days in Chicago and crossing paths with the likes of John Belushi, Steve Goodman and Kris Kristofferson. They also talked songwriting, improvisational comedy, record deals, friendship, and much more.

On Getting Started

Prine: Soon as I could play one guitar chord and laid my ear upon that wood, I was gone. My soul was sold. Music was everything from then on. I’d listen to that chord as long as it would linger.

Murray: First time I went to class at Second City, I was so bad that I walked out to the street, and just kept walking. Then I hitchhiked around the country. When I came back, I could do it. I had to go out and live some before I could stand in my own shoes onstage and feel confident.

Prine: I was 22, working as a mailman, doing the open mike night. I wrote “Souvenirs” in the car on the way.
Cooper: How did you know at your age all about longing and, regret?

Prine: Man, I’ve known about that since my first pair of shoes. You know that first love that leaves you? You never forget that, especially if you’re a songwriter. I must have gotten nine songs out of that girl.

<iframe width="620" height="349" src="https://www.youtube.com/embed/lccFpJjS3N8" frameborder="0" allow="autoplay; encrypted-media" allowfullscreen></iframe>

On Steve Goodman

Prine: [Goodman] was 5 feet 2 of dynamite. He was a ball of energy. Also the hardest person I’ve ever followed onstage. Steve would just drain the audience. They would have no bones on them after. Then he’d walk offstage, hit me on the shoulder, and say, “They’re gonna love you, Johnny.”

Murray: Sometimes I’d be done at Second City and they’d still be going at The Earl, so I’d stumble by to hear Prine or Steve Goodman. By then they’d already manipulated the crowd. There were men that were crying, and women who were just adoring. Musicians! They work their ways.

On Struggling To Survive

Murray: I had to get out the house. We lived in the suburbs and I was not welcome in my own house, because I was a troublemaker. I had a schedule worked out where I’d get in late, sleep past when everyone would leave, wake up, eat all the eggs I could, feed the dogs, and leave before they came back. Then I’d be out all night and come back and go to sleep before they left.

I’d go to Old Town, where my brother took care of me. I watched the shows at Second City a lot. It was Belushi, John Candy, my brother [Brian Doyle Murray]. and his friends. I’d hitchhike back and forth, because I had no money. And hitchhiking in Chicago in the winter is a ridiculous proposition. Somehow I made it home.

Prine: My goal was getting out of the post-office. I was a mailman walking in the snow six days a week, 12-hour days. Every two weeks I’d get a check for $228. Earl of the Earl of Old Town told me, “If you sing four nights a week, I’ll give you a thousand bucks cash under the table.” I thought, this is heaven!  Once I got out, I was King of the Hill!  I slept late all week and made a thousand dollars a week! I didn’t care if I never did anything else. I was a total 100% success. That was as far as I wanted to go. I didn’t think of getting a record deal.

On Finding Success

Murray: I was onstage at Second City and I did something in a scene, and I could feel it in me; I felt it react and rebound with the audience. It hit me I could support myself by doing this.

<iframe width="620" height="349" src="https://www.youtube.com/embed/ZIRyWlPi7Fc" frameborder="0" allow="autoplay; encrypted-media" allowfullscreen></iframe>

Prine: Kris Kristofferson and Steve Goodman were the two most unselfish people I ever met. Kris loved Steve, and said he needed to go to Nashville to make a record. Goodman said, “No. You need to go hear my buddy, John Prine.”

So at one in the morning on a Sunday they came to the Earl and I sang. Then Kris asked me to sing them again and said I was going to New York, too. Goodman and I went to New York, straight to the Bitter End. We see Kris, who told us we were each going to sing three songs a piece. Jerry Wexler came up after and asked me to come over to Atlantic the next morning at 10 am. I did, and he had a record contract on his desk waiting for me. I hadn’t been in New York 24 hours.

Back then in Chicago, you had to leave town to get a deal. Me and Goodman left town for three days and came back with record contracts. We were like returning astronauts! I never knew that wasn’t the way it went. I wondered for years why my peers kept their distance from me. It’s cause I was the Cinderella kid. And I was lucky.

Murray: These guys are ice-breakers. Kristofferson for you. Belushi was mine. He dragged all of us to New York for the National Lampoon radio show. Belushi broke it open for a lot of people and made it possible for find the opportunities. I was lucky. The spotlight would be on them, and I’d be the spare-part, like if they needed an extra bride-groom. I was lucky all the way.

Janelle Monáe On Choosing "Freedom Over Fear" & Creating 'Dirty Computer'
 

Like many of his peers, Charles Esten has known music is his calling since he was a kid. But at 58, he's just now getting the opportunity to do what his contemporaries are long past: release a debut album.

As fans of the beloved ABC/CMT series "Nashville" or the hit Netflix drama "Outer Banks" know, Esten first established himself in the acting world. But as his "Nashville" role revealed, the actor also had some strong singing chops, too — and it wasn't a coincidence.

Due Jan. 26, Love Ain't Pretty is a testament to both Esten's patience and his passion. Combining his soulful country sound and emotive songwriting, Love Ain't Pretty poignantly captures his years of loving and learning. And with a co-writing credit on all 14 tracks, the album is the purest representation of his artistry possible.

"Being the age I am, and the difference of what this album is to what maybe my first album would've been if I was 28, is the intentionality," he tells GRAMMY.com. "I can chase what's thoroughly me, and the facets of that. And in the end, that, I think, makes better music anyway."

As the title suggests, Love Ain't Pretty mostly focuses on finding the beauty in life. Along with several odes to his wife, Patty ("One Good Move," "Candlelight"), Esten delivers tales of self-reflection ("A Little Right Now") and simply enjoying the moment ("Willing To Try"), all with a grit that's equal parts inspiring and charming.

Perhaps the most fitting sentiment on the album is "Make You Happy" — not because of its lovestruck narrative, but because it captures Esten's goal with Love Ain't Pretty and beyond: "Wanna make you happy/ Wanna make you smile."

"I know that musical superstardom is not an option," he acknowledges. "I don't even seek it. So, what do I seek instead of perfection? Connection."

Below, Esten recounts his fateful journey to Love Ain't Pretty — from his first taste of stardom to finally fulfilling his lifelong dream.

This interview has been edited for clarity.

View this post on Instagram

A post shared by Charles Esten (@charlesesten)

All the way back in third grade, our elementary school had a contest to write the school song. They said, "Find a Disney song and use the melody and then put new words to it." I did it to "It's a Small World." I probably wrote little doodles on my own [before that], but that was the first one with any bit of fame. 

I went back, like 10 years later, and they were singing that. They actually made it as part of all the assemblies and everything. That feeling, to hear people singing words that you thought of, I'm sure that was the beginning of this path.

Eventually, when I went to college, I was in a band. But, even before I was in a band, my grandmother passed in my sophomore year of college. And, I didn't get back in time to see her. She had helped raise me when I was little, after my parents' divorce, so it hit me hard. I somehow was able to put what she meant to me in a song, and that made a big impact in a lot of ways. Whereas that third grade little ditty made everybody laugh and smile and everything, this made my mother and my aunts and uncles [cry] in a warm, loving way. I could see it affecting them. 

I could [also] feel it help me process what I was going through. That was another bit of an aha moment, like, "Oh wow, writing a song can do that also."

Right after that, I started a band. That experience of hearing a band bring your song alive — it was so much more full, this experience, and hearing somebody else add a thing you hadn't thought of, that was another true revelation, the power of that. So I got hooked rather quickly. 

Honestly, I probably would've stayed in that world if my band had stayed in that world. They all made the decision to graduate and go be doctors and lawyers and stuff, as the song says. When that finished up, I didn't know what I was going to do next. But, having experienced that made it clear to me that I was not cut out for a desk job — even though I had an economics degree. 

I had some friends that had gone to L.A. and started becoming actors. I thought, "Maybe I'll give that a try." But the long and the short of it is, if you had asked me, "Will you continue in music?" I'd be like, "Absolutely. I'm going to go out there and I'm going to meet another bass player and a drummer and another band will come."

It didn't happen. I went to London and played Buddy Holly for two and a half years in the musical "Buddy." When I went back to L.A. after that, then the family started to come, and so the band just never happened. But I had a piano, had guitars — I never stopped writing or playing.

At one point, I had the thought, "Well, I might have missed the boat in terms of ever getting to be a performer myself, but I can write songs." And by this point, I was really listening to a whole lot of country, '90s country, 2000s and all.

So, I decided I was going to start writing in a more formalized way, in a more intentional way, instead of just whenever a song came to me. And, as soon as I sort of said that, things started happening.

I met my friend Jane Bach, who is a great Nashville songwriter. She was going back and forth between LA and Nashville at the time. She invited me to sing at the Bluebird [Cafe in Nashville], which I knew very well, and I said yes. And twice, I had to cancel because I got other work. And at a certain point, I literally said to my wife, "When am I going to get to go to Nashville? That'll never happen."

[That] maybe was two or three years before "Nashville." And then I get this script that says, "Nashville." Next thing I know, I'm here and I'm literally doing my first scene in the Bluebird.

I understand, very cleanly, that ["Nashville"] opened all these side doors that most people don't have access to. But, I also know that there's a chance they could have all been opened and I could not have been ready. 

When it finally [happened], for a lot of people, just looking at an actor who's playing a singer/songwriter, I get the feeling that it was a pleasant surprise — I like to think that there was a little more there than they expected. It was actually more authentically who I was than the actor.

I never really quite verbalized this, but the feeling [of landing "Nashville"] was one of — it'll make me emotional — completion. I felt like the show was an answer to so many unsolved things in my life. And that's, I think, why we haven't left. And it's also why the album meant so much to me.

It meant so much to me that I didn't just get here and do an album. I got here at 46. To be that old and not really know who you are as an artist — I never had to define myself. So, I didn't chase that immediately. I just wanted to make music in Music City and make as much as I could. 

I always felt behind, because all my contemporaries that had been here, very many of them were already incredibly famous and already had done so much. But you can't [focus on] the road not taken. 

I have to admit, there's some part of me that would be like, "What if you were putting out your first album at 28?" That's nothing I sort of worry about. I know that it wouldn't have been this. I wouldn't change anything. I have this wife and this family and this career that brought me here. It feels like this was the way it was meant to happen, as strange as it all is.

I felt more prepared than people might expect. And I had something that most people didn't have, which was, Deacon walked in places before I did. Deacon sang at the Bluebird before Charles did. Deacon was at the Grand Ole Opry before I was.

That began what I would call my 10,000 hours in this town. Between the number of hours I've been able to be on stage at these incredible venues, and play music with these incredible people, and all the singles I was able to put out over the last 10 years, I now feel like that, in some ways, I have as much of a catalog as people that have been here for those 30 years. But, it's still my first album, which I've held onto for something special, and I'm so grateful for the way it turned out. I couldn't be happier.

I knew that I wasn't emptying the whole toolbox to play Deacon. But, having said that, I'm so moved by how much playing that guy influenced my music and my songwriting. A song like "A Little Right Now," it roars at the top and rages a little bit, but in general, that is a Deacon song through and through. "I'm a farmer praying for rain/ I'm a gambler that needs an ace of spades/ I'm a sailor hoping for a gust of wind/ I'm a singer looking for that song/ I'm a prisoner that ain't got long/ I'm a dreamer waiting for my ship to come in/ But lately all my roads have been running out/ There ain't no silver linings in these clouds/ Help me, Lord, and show me how to find the kind of faith that I once found/ 'Cause I could sure use a little right now." When you watch the show, you'll go, "That's the Deacon-est thing I've ever heard."

There's other songs on this album as well. "Maybe I'm Alright" — Deacon's journey was from utterly broken to "maybe I'm alright." As I look at it, he informs this album.

I'm a procrastinator. That's why I released so many singles in 2016, that world record. [Editor's note: Esten released 54 original songs once a week for 54 straight weeks, earning a Guinness World Records title in 2018 for the "Most consecutive weeks to release an original digital single by a music act."] 

That was a mind hack — a life hack — to arbitrarily create deadlines. And, my God, did that work, because I just started putting it out. [After that,] I started thinking about an album, and I even made an early attempt at it, and then COVID hit. 

They felt like songs from a thousand years ago [after the lockdown]. I pretty much scrapped it and didn't use any of them, and said, "I've just got to do this again in a different way. It's a different me. It's a different world."

My wife is not a procrastinator. And I'll show her, sometimes there's an upside of procrastinating. It's like using a crockpot when there's a microwave right there — it stews in all the ingredients. 

Deacon's a major ingredient, but if you just put that major ingredient on it and cook it real quick, it's too pronounced. Stew it in there with all the other ones until it's a new flavor, a new thing in its entirety. And that's what happened.

It's also interesting that, being the age I am, and the difference of what this album was to what, maybe, my first album would've been if I was 28, is the intentionality in terms of radio success or chart success — or chasing something that might not be thoroughly you, but might be a little more popular than thoroughly you. There's no reason for it at my age, so I can chase what's thoroughly me, and the facets of that. And in the end, that, I think, makes better music anyway.

There's a video I put out for "Somewhere in the Sunshine." Already, the impact of that song is sort of blowing my mind. The video is full of quotes from people that commented on YouTube about who they lost, and how it's giving them a little moment of peace, and how it's blessing them. That's my radio play. That's my GRAMMY.

I try to always realize how blessed I am to be able to do this. It's so much more precious later in life. I think people sometimes meet me and I have an enthusiasm for it that is younger than my years. And, maybe [that's] just because I've been waiting at a distance so long and it finally came true. I might get jaded someday, but it hasn't happened yet.

There's still an outsider mentality. I also feel like an anomaly. All the great artist friends I have, I'm not like them. They've been on the radio, they've had cuts, they've had hits. And then, all the new ones starting off doing their first album, I'm not in their group either — they have a whole career and future ahead.

On the other hand, I feel warm and welcomed in all of those arenas, and in everyone in this town. It always has been unusual for me here. All the reasons I'm here, all the why's, all the how's — but I guess, in the end, that's how I fit, and that's how I belong.

I was blessed that I was able to take my time. I think, once you let go of the outcome, freedom is available. It's just really hard to let go of that outcome. But, as I said, I'm a different beast. What I am means I better let go of that outcome, because the odds of me getting a No. 1 smash off this, they're not great. But the odds of me moving somebody with this music? I think they're pretty good.

2023 In Review: 5 Trends That Defined Country Music

Updated Friday Oct. 13, 2023 to include info about Kendrick Lamar's most recent GRAMMY wins, as of the 2023 GRAMMYs.

A GRAMMY veteran these days, Kendrick Lamar has won 17 GRAMMYs and has received 47 GRAMMY nominations overall. A sizable chunk of his trophies came from the 58th annual GRAMMY Awards in 2016, when he walked away with five — including his first-ever win in the Best Rap Album category.

This installment of GRAMMY Rewind turns back the clock to 2016, revisiting Lamar's acceptance speech upon winning Best Rap Album for To Pimp A Butterfly. Though Lamar was alone on stage, he made it clear that he wouldn't be at the top of his game without the help of a broad support system. 

"First off, all glory to God, that's for sure," he said, kicking off a speech that went on to thank his parents, who he described as his "those who gave me the responsibility of knowing, of accepting the good with the bad."

Looking for more GRAMMYs news? The 2024 GRAMMY nominations are here!

He also extended his love and gratitude to his fiancée, Whitney Alford, and shouted out his Top Dawg Entertainment labelmates. Lamar specifically praised Top Dawg's CEO, Anthony Tiffith, for finding and developing raw talent that might not otherwise get the chance to pursue their musical dreams.

"We'd never forget that: Taking these kids out of the projects, out of Compton, and putting them right here on this stage, to be the best that they can be," Lamar — a Compton native himself — continued, leading into an impassioned conclusion spotlighting some of the cornerstone rap albums that came before To Pimp a Butterfly.

"Hip-hop. Ice Cube. This is for hip-hop," he said. "This is for Snoop Dogg, Doggystyle. This is for Illmatic, this is for Nas. We will live forever. Believe that."

To Pimp a Butterfly singles "Alright" and "These Walls" earned Lamar three more GRAMMYs that night, the former winning Best Rap Performance and Best Rap Song and the latter taking Best Rap/Sung Collaboration (the song features Bilal, Anna Wise and Thundercat). He also won Best Music Video for the remix of Taylor Swift's "Bad Blood." 

Lamar has since won Best Rap Album two more times, taking home the golden gramophone in 2018 for his blockbuster LP DAMN., and in 2023 for his bold fifth album, Mr. Morale & the Big Steppers.

Watch Lamar's full acceptance speech above, and check back at GRAMMY.com every Friday for more GRAMMY Rewind episodes. 

10 Essential Facts To Know About GRAMMY-Winning Rapper J. Cole

Living Legends is a series that spotlights icons in music who are still going strong today. This week, GRAMMY.com spoke with Swamp Dogg, the eccentric soul and R&B titan still actively writing, recording and performing more than half a century after his debut album.

Swamp Dogg is about to play a major concert in New York City, and he has a few commitments to keep.

There will be no medleys. He won't talk down to the audience. When he hits a bad note — which he calls a "guaranteed" prospect — he'll pause, reassess and fix it.

"When they leave, they're not thinking much about the bad note, because we all talked about it in this conversation," the artist born Jerry Williams, Jr. tells GRAMMY.com. "I do have a conversation with my audience, and it's good."

That gig, at Knockdown Center in Queens on July 28, should serve as a reminder that Swamp Dogg has been in a strange, wonderful dialogue with the planet from the jump. This dates back to when he made his first recording, "HTD Blues (Hardsick Troublesome Downout Blues)," in 1954 — an awfully pessimistic dispatch from a 12-year-old.

His 1970 debut under the moniker, Total Destruction To Your Mind, is a fantastic slice of left-field psychedelic soul — filled with fried, occasionally conspiratorial, frequently profound insights that framed him as something of a modern prophet. ("Why wasn't I born with orange skin/ And green hair/ Like the rest of the people in the world?" remains an excellent question.)

In the ensuing decades, Swamp Dogg (he spelled with a double g before Snoop Dogg was born) has released numerous albums; naturally, his career has ebbed and flowed.

But at 81, he's found indie stars like Justin Vernon and Jenny Lewis in his corner, and released inspired late-period albums like 2020's Sorry You Couldn't Make It and 2022's I Need a Job… So I Can Buy More Auto-Tune.

Ahead of the Knockdown Center show, read on for an interview with Swamp Dogg about his live philosophy, upcoming music, profound relationship with John Prine, and decidedly so-so relationship with… the state of Rhode Island.

---

This interview has been edited for clarity.

What can people expect from your upcoming Knockdown Center gig?

To be honest with you, I don't know, other than I always try to give the last drop of whatever I'm doing. I don't do medleys and that bulls—. They can expect to get it all, and I usually try to get in as many songs as I can without trying to get the audience out of the way.

You feed off the energy of the crowd like a consummate performer should. You're not rushing through it or phoning it in.

Right. Plus, usually, I talk to my audience. Not just to hear myself talk. I get the audience involved. Not a lot of mundane s—. I talk to them like we live together. If you had somebody else in your house, the way you would talk.

When you launched your career all those decades ago, which performers galvanized you to give your all?

It's funny: one of the artists that inspired me the most — and kind of encouraged me, without knowing me, to give everything — was Chuck Berry. Chuck didn't have to do anything but be Chuck, and, damn: that's all you wanted.

Chuck did his singular thing as long as he could possibly do it. Every performance was pure, uncut Chuck. I see that quality in you as well.

Right. If I'm doing a song and we hit a bad note — sometimes a note that's haunting, it's so f—ing bad — I'll stop my band, and talk to my band. I'll take three or four minutes and give the audience what I want.

What can you tell me about the musicians who will accompany you at Knockdown Center?

I've got some great musicians right now, for the gigs I'm doing over the next six weeks. They've been with me for a while.

My keyboard man plays loop stuff. He plays just about every instrument there is. He'll cover for me, because I will hit a bad note. I guarantee I'll hit a bad note. But I'll make up for it. And it's not going to be bad notes all night long. [Laughs]

Human error is how I look at it. But I work real hard to make sure that my audience is happy. I'll stay out on stage as long as the house itself is fine with what I'm doing.

And you have some shows after Knockdown Center on the books, too.

I know we're playing in Rhode Island and some other things coming up. I don't know anybody who ever played in Rhode Island. Nobody ever says, "Hey, let's go to Rhode Island!" It's like, f— Rhode Island.

Don't get me wrong; that doesn't mean Rhode Island is a bad place. It's just musically, you never hear of anybody going there. 

I'm looking forward to it, because how many chances do you get to go to Rhode Island? But there are more memorable states for sure. You don't hear it on quiz shows. I guess if you did, it would be [the result of] the most complicated f—ing question you ever heard.

*Swamp Dogg. Photo: Rich Fury/Getty Images*

What are you working on lately? Can we expect new music coming up?

I've got an album that's finished. It's a country album, and it's great. It's just that I've got to get the liner notes together, because it's got a lot of s— in it as far as information.

I'm not using a drummer at all, but you're not going to miss it. Because if you listen back to the old, old stuff, they didn't have a set of drums. So, I left the drums; I'm trying to go back to the beginning.

On a different note, it was bittersweet to hear John Prine on Sorry You Couldn't Make It. That had to be one of his final recordings. What was it like working with him?

He was a very real person. He and I had planned to go to Ireland together, because he had a house in Ireland. We were going [to go] there for about a week and just write our asses off.

I miss him. I'd known him since sometime in the '60s. We had a lot of stuff we wanted to track lyric-wise, but I guess music-wise also. Good guy, filled with talent.

Which Prine song means the most to you?

"Sam Stone."

Yeah, I know you covered it.

I do it every show. There's a different ending every time I do it, because it's one of those songs that gives me a chance to talk to my audience about how things are, what's going on, what I feel we could do for the country, and to make people more comfortable.

Like giving away clothes. Some people forget that if you put a bunch of clothes away a few years, and moths haven't eaten the s— [out of them], you could give it to these people. And don't be ashamed of the money you can't give — just be happy about what you can give.

I see all the problems that we have, that are unnecessary. That's what makes me really get into "Sam Stone." Usually, 90 percent of the time, I am with Sam Stone.

It's like a preacher on Sunday morning. He preaches and it is basically the same s—, but delivered in a different way. So, that's what I'm doing.

What did you think when Johnny Cash covered "Sam Stone" and controversially changed the lyric "Jesus Christ died for nothing, I suppose" to "Daddy must have hurt a lot back then, I suppose"? Some say that carved out the meaning of the song.

I've never heard it. I like Johnny Cash. But there are about 10 country artists that I like better.

Living Legends: Van Morrison On New Album Moving On Skiffle, Communing With His Roots & Reconnecting With Audiences

Singer/songwriter Tommy Prine’s debut album is joyful, introspective and angry — just the emotional mix you might expect from someone who’s lost his  father and best friend, toured internationally, and released an album, all before turning 30.

Losing a parent is a profound, painful experience, doubly so when your dad is the musical inspiration John Prine. Filling those shoes would be impossible, and Prine doesn’t want to. Instead, he’s written a deeply personal, decidedly individual album, which in no uncertain terms tells the world that he is not riding his father’s coattails.

Out June 23, This Far South opens with an unapologetically fiery, soul-searching disquisition. The 27-year-old Prine encourages the listener to consider the meaning and existence of God, and to sit with the confusion and frustration inherent to processing pain. From there, Prine takes off on a personal and professional artistic journey.

He’s both sweet and thoughtful on This Far South, slowly releasing his anger as he probes rock bottom, ruminates on a panic attack and the hazy malaise of the pandemic. Mid-album, Prine takes a goofy trip with the punk-rock infused "Mirror and a Kitchen Sink," and longs for bygone mundane moments in "Boyhood" and "By the Way," his ode to his father. Prine ends the album triumphant in his independence on "Cash Carter Hill" and with a love letter to his wife, Savannah: "I Love You Always."  

Becoming an artist wasn’t a given for Prine, who didn’t consider the career path strongly until late in 2019 when he played an impromptu solo set at All the Best Fest in the Dominican Republic. During the pandemic and after losing his dad in April 2020, Prine began writing more; in November of 2020, singer/songwriter Ruston Kelly and sound engineer Gina Johnson talked Prine into cutting an album.

"It was the most excited I've ever been in my entire life," Prine told GRAMMY.com. "I think I needed that from someone outside of  my family that I loved and trusted; I needed that validation."

Growing up, like most teenagers, Prine looked for music that was different than his parents’. He listened to a variety of artists including Jason Isbell, System of a Down, ATLiens, Outkast and Gorillaz, dabbled in EDM, and fondly recalls driving to school with his big brother in the family’s ’85 Ford Bronco blasting Eminem’s The Slim Shady LP. Reflecting his varied musical tastes, This Far South samples auditory flavors from punk rock, pop, and folk and Americana.

Prine spoke with GRAMMY.com after wrapping up a tour, which included sold-out shows opening for Tyler Childers, and his first residency at The Basement in Nashville (with special guests including Amanda Shires and Katie Pruit). He detailed finding inspiration and humor in life’s seemingly insignificant moments, his struggles to process loss, how he took control of his artistic image, and why his music is different than that of his father.

I imagine music was quite present in your household growing up. What are your early memories of listening to music?

Music was just always in the household. My dad was a firm believer in A.M. radio; he'd just have that playing 24/7. And he'd be telling me about all these old country songs. 

And me and my brothers, we were all given the space to make our own relationship with music. There wasn't a certain type or a certain record or anything that my parents would be like, "Oh, you guys should only listen to this" or whatever. And I think that was really beneficial.

Growing up, I was listening to so much random stuff. I'd have a couple of months where I would violently switch between genres: like metal, and then classic rock, and then I listened to EDM for a couple of years. I’d say the record that that made the biggest impact on me in terms of what I'm doing now was Southeastern, Jason Isbell's record. It ripped my heart open and put it back together in an hour or so.

Tell me about starting to play music yourself.

I was a really little kid when I picked up the guitar, I think I was just kind of mimicking my father. And family friends that would come over and play music. A majority of how I took in the adult world was adults playing music. I thought that's what everyone did. So I was like well, I better start now. 

So I picked up a guitar and would hit it and make noise. And then I just instantly fell in love with it. So I've been playing guitar really my whole life. I started writing my own songs, probably at 16 or 17. But I wouldn't dare show them to anybody until 19 or 20. That's when I started making my own music.

I've read elsewhere that you didn't really write music to share with people until after you lost your dad. 

There were like a very select few of my buddies that I would play my songs for when they came over. I was pretty shy about it, as most people are. It's a pretty vulnerable thing to be writing a song and then showing somebody, let alone my parents. I would never show them really much until just the last few years.

So then what changed for you?

I don't know what it was. A majority of my life [now] is sharing my heart and my mind and putting it on display for the world. 

I think that every artist would probably say the same thing: it's almost out of necessity. It's just so much going on inside that it has to come out and I have to play it. And I have to show other people to make a connection with it or else I'll just go crazy. I think it was just bursting at the seams with all the things that I wanted to say. And I've always found it easier to tell my story through a song rather than actually talk about it.

I think that was late 2019 when I started seriously thinking about [sharing my music]. I played an impromptu set at All the Best Fest in the Dominican Republic. And I played like a 40-45 minutes set and most of it was originals. As nerve wracking as it was, I was like, wait, I really thoroughly enjoyed that. And I remember walking off the stage, and I had this weird feeling of being more comfortable in my skin than I ever had been.

It sounds as though you were understandably a little bit reluctant to choose a career as a musician. Can you talk about that hesitation and getting over the hump?

I think most people will probably look at it and be like, oh, of course he was because of who his father was and how big of a career he had. It wasn't that, it was really just the ins and outs of the day-to-day life that I knew artists went through. It's a hard job — you're traveling a lot; it's pretty taxing on your mind and your emotions, your body. And I saw what that did to my dad and…it just felt like this big, massive, insurmountable mountain that I didn't even want to start.

I kind of always just gave myself a reason to be like that's not you. The negative self talk which, surprise, surprise doesn't go away, even when you become an artist, is still thriving. But I think being able to look into the face of that version of yourself telling you that you can't do it is pretty empowering.

You don't want to be seen as John Prine Jr. obviously, but also, your dad is an inspiration to you as well. How do you hold space for both those ways of relating to him?

I've always made the distinction, even when I was a kid. There's John Prine and then there's dad. Of course, they're one in the same, but when my father would go out on the road, it was kind of like a switch. He would flip and go into his John Prine personae and go out there and play shows for the world and be who he was, an amazing songwriter, singer/songwriter and artist. And then when he was home, he'd be like, "Hey, buddy, you want pancakes?" And we'd sit down and talk about movies and stuff.

One thing that I hear a lot of artists struggle with is that there isn't ever going to be that many people in your life that can fully understand what you're going through and what you're doing. And it does kind of suck because I have a million questions that I'd like to ask him. And he would be the greatest source of information on this kind of thing. But I'm really lucky that I get to listen to his songs, watch interviews, and learn from that.

I don't know if there's really a way for me to put into words the inspiration that my father has given me. I mean, I'm 50 percent of him. I share DNA. So he's inspired more than just my songwriting and my singing and artistry, he's inspired me to be a good human and he helped raise me. 

They say people end up turning into their parents, the older you get. So I think I'm answering that question just by being alive and figuring things out about myself.

I'm curious about the very first single that you released, "Ships in the Harbor," which isn’t on the album. How did that song come to be?

Well, it was after I recorded the record, so that's why it's not on the album. I had only been on the road for just a couple of months at that point. And I was home and it was really pretty outside. So me and my wife and my dog were just kind of chillin’ in the backyard. And I just started picking around and that melody was floating around my head. It was near my birthday. And whenever it's near my birthday, I always get super pensive, introspective, thinking about time and all that fun shit.

And I had this thought that we as humans have the capacity to feel all these crazy, strong emotions and loving people, and missing people, and fear. And I had a thought that the only reason that we're able to feel as deeply in those emotions is because everything that we experience is finite, including our own lives. If the things we loved, the things that we experienced in our life, were around forever, I don't think we'd be able to feel as strongly as we do about them. 

We always look at cardinals and blue jays, blue birds because it's a big thing in my family – if we see one it’s someone looking after us. And that's where the second line came from. So I just kept going. 

I was getting really emotional towards the end of the song, and I didn't understand why. And then that last verse came out, and I was like, okay, this is what I'm getting at here. So, that one was a tough one to write but I'm glad I did. 

It's a beautiful song. Why cardinals and bluejays?

My grandma on my dad's side, his mom, when she was passing away she said if I see a cardinal or a blue jay, it’s her looking after me. And she had pictures of them all over our house. So I ended up getting a big blue jay tattoo on my right arm for my dad's side of the family. And then I have one for my mom's side. It's an ogham, it's an ancient Celtic scripture. It's love in Gaelic. So I have something for my mom and for my dad.

And speaking of powerful moments, when did you perform for people first?

The first time I ever performed on stage was at a sold out Ryman Auditorium show with my dad, I think it was [with] Jason Isbell, when I was a junior or senior in high school, and I just fell in love with it. So I started doing the encores with my dad and then I would sell merch before and during the shows. I just loved it. 

It was a lot of really amazing experiences and I got to play some really cool venues with him. And now I have this thing in my head where I'm like alright, I gotta get back there and do my own songs.

I'm curious about the opening track of the album, "Elohim," which is profound and angry. And it's an interesting place to start off an album. Why start there?

I wrote it from a place when I was still really struggling with the loss of my father, and I lost my best friend to an overdose in 2017. And that obviously had a very profound impact on me, and the way that I saw the world.

I struggled for several years with my own personal faith, and why things happen. There was a long time where I thought that we were all just kind of living in this state of limbo. And I wrote that song from a very angry space — just questioning whatever is the omnipotent force that is looking over us, like, Why did I have to go through these things? It doesn't seem like I'm learning anything. It's just like I'm in pain.

And I wanted to start the record that way because the album is a story of me. It's the introduction of Tommy Prine to the world and my formative years and why I am the way I am. And it starts with "Elohim," this big, loud, angry song of me not really even interested in figuring things out. I think that that's a really powerful thing that everyone should know: that it's okay to just

 be angry and not have answers. You're doing the good work by letting yourself feel those things.The record kind of moves through from there to me talking about how I don't want to go back to the person I was when I was partying all the time and needing to grow up. And then I start talking about my anxieties and panic attacks. And then I start talking about my family and I'm kind of coming back to my roots a little bit and getting closer with them and talking to them about my life experiences. And then the album ends with a song about my wife. We got married last year, so it's my story of basically entering manhood.

"I Love You Always," the album’s final track, is pretty far from "Elohim." There's also these sweeter and lighter moments on the album, like "Boyhood." I'm particularly curious about "Mirror and a Kitchen Sink"; it’s been stuck in my head for days.

So funny enough, that was actually the first song that I wrote after my dad died. It was literally within the next 72 hours that I picked up the guitar. I was like, why am I writing this goofy sort of punk rock song? 

The song is about how I find myself  arguing with myself a lot of the time. I’ll be thinking of these people that don't exist, and then a conversation that I would have with these people and …how to win an argument that I'll never have. And then I realized I'm literally just arguing with myself. And the only thing that's in the room is me, a mirror and the kitchen sink. 

The album also covers a lot of musical territory, can you describe that variety a bit?

To me, there's three distinct vibes on the album: There's the loud rock songs, anthemic, big songs, where I'm kind of getting a lot off my chest. There's the alternative folk/Americana [songs] where I'm getting really introspective. After getting things off my chest, it's like the questions that I come up with, I kind of dive into those and work some of that out. And then there's the dedication songs — like the one for my dad, the one for my wife, "Letter to my Brother," for my friends that are going through hard times and I'm just telling them that I'm there for them.

I had such eclectic music tastes growing up that there is never one overruling genre that I would ever listen to. But to me it all made sense and was a cohesive thing. And that’s really hats off to Gena and Ruston and that they were able to take all my insane ideas and put it into something that I love. I'm happy that I did it that way with the first record. Because I feel like I can go wherever I want to go now with record two.

Is record two on the horizon?

I probably have enough to make record two right now in terms of songs. I'm taking my time with it, just because the first one isn't even released and I'm trying not to get ahead of myself. I've been thinking about record two for a while, it'll happen whenever it's time.

Can you lay that out, how you would like people to understand you as an independent artist and as your dad's son?

Well, honestly, I really think that the music speaks for itself in that regard. I think that there's some pretty obvious parallels and some times where it intersects, just in my turns of phrase and the way I go about explaining things, or sometimes the in simplicity of the lyrics where people can be like, ‘oh, yeah, like, that sounds like something John Prine's kid would do.’ And I honor that and I fully take that on. I'm never not going to be his son.

But also I grew up in a very different world than he did, I have very different experiences than he did. And when you're making music and you're writing your own songs, that is also going to come through. One big difference is my father was a really amazing character writer.. And through the stories that he would form with these characters were little bits and pieces of him in it. And I think that was something that people had to figure out.

Whereas I'm just straight up talking from my perspective and I'm talking about my life and things that have happened to me and how I felt about it. I think if you come to a show or you listen to the music, you'll see that I'm just Tommy, I'm not John Prine jr. I care about the people that like the song "Elohim," and like "This Far South," because it makes them feel less alone because of my story, rather than like, oh, John Prine’s kid also makes music, this is cool.

And I had to get over that day one starting block before I even did this. I'm just me being me, and if people find similarities, cool, if they don't, good, you're listening.

On 'Weathervanes,' Jason Isbell Accepts His Internal Pressures And Fears