The Pollstar Interview: Legendary Singer/Songwriter Steve Earle Takes Off The Mask
Cover of Pollstar: Steve Earle & The Dukes are pictured at Tipitina’s in New Orleans on May 1, 2018. (Photo by Steven Hatley

DECATUR, Ala. – It’s June 1, which means it’s launch day of the 2022 tour for Steve Earle & the Dukes, with the first stop being the Princess Theater here. It’s also the first day on the job for new tour manager Cole Taylor, who escorts Pollstar to see the legendary singer/songwriter back-of-house, just prior to soundcheck. The vibe is chill, and Earle awaits in a production room, sipping on a bottle of Perrier and eager to get the conversation going so he can knock out the soundcheck, and begin in earnest a full tour in support of his May release, Jerry Jeff, the third in a trilogy of tributes to his mentors. The other two in the series would be Guy from 2019 and Townes from 2009, tributes to the great Guy Clark and Townes Van Zandt, respectively.

In a career marked by artistic triumphs and a somewhat chaotic personal history, Earle remains a creative force to be reckoned with 36 years after exploding into prominence with his debut 1986 album, Guitar Town, on MCA. Three more well-received records followed, including the landmark Copperhead Road, and Earle began to move up the venue headlining hierarchy. But as the next decade began, his bad drug habits, run-ins with the law, and lack of creative production led many to believe his run would be a short one.

Lead Photo Steve Earle Danny Clinch
Photo of Steve Earle by Danny Clinch

Instead of ending up dead or doing hard time, Earle got clean and began a remarkably prolific run that has cemented his status as one of America’s most revered singer/songwriter.
Now far removed from the fresh-faced maverick that turned Nashville on its ear, as well as the rail-thin, unpredictable addict that followed, today’s bushy-bearded, robust Earle retains his leftist politics and fierce commitment to social justice that has always been at his core. That stance has probably cost him some fans along the way, especially certain of those who came aboard for the Southern-rock tinged “Copperhead Road” era in 1988. That’s fine with Earle, who really has no filter and still calls it as he sees it, and if it has cost him a few friends along the way (and, perhaps, marriages), well, that stings a bit more.

All that said, 20 years beyond his most troubled times, Earle, now 67, is clear-eyed and focused on his career path, the deep lines on his face betraying a youthful energy. With the help of manager Danny Goldberg and Jesse Bauer at Gold Village and agent Lance Roberts at UTA in Nashville, Earle is able to focus on songwriting and performing, and also his other creative pursuits which include author, playwright, actor, painter, and whatever else might help him provide for John Henry, his 12-year-old, autistic son with ex-wife Allison Moorer.

An unabashed Bernie Sanders socialist, Earle is a capitalist as it pertains to turning his considerable talents into a revenue generator in support of his son. Over the past two decades, Earle has settled into a rhythm that can fill good-sized theaters in most markets (not, however, this one), and he remains a powerful festival booking that still can add juice to a lineup. Over the past decade, Earle averages more than $25,000 per show, according to data reported to Pollstar, with average ticket sales near 1,000 per show.

This night at the 677-cap Princess Theatre, a less-than-capacity crowd is never less than fully enthusiastic in support of Earle. As a performer, Earle is old-school, supporting his latest release with nearly a third of the 30-song set from Jerry Jeff. Of his own vast portfolio of songs, “Someday” and the title cut from Guitar Town, along with “Copperhead Road” are vigorously received, as is lesser-known material like “Transcendental Blues,” a tender “Goodbye,” and the rarely played “The Week of Living Dangerously” from 1987’s Exit O. It’s a well-paced, energetic set, with the current version of The Dukes skillfully veering seamlessly with Earle from Celtic to Texas honky-tonk, blues, bluegrass, country and rock. Earle plays guitar, mandolin, and harmonica, with the rest of the band made up of Chris Masterson (guitar, mandolin, vocals), Eleanor Whitmore (fiddle, mandolin), Ricky Ray Jackson (pedal steel, dobro), Jeff Hill (acoustic and electric bass, cello), and Brad Pemberton (drums, percussion). Whitmore and her sister, Bonnie, opened the show as The Whitmore Sisters. This show is one of hundreds of all types that go on across America every night, unheralded, with zero hype but, at times, transcendent, everything that live music is supposed to be.

Five hours earlier, the quintessential “hard-core troubadour” that is Earle darts from topic to topic as he holds forth for
Pollstar on topics as varied as Texas history, labor unions, organized crime, segregation, American journalism, Broadway, parenthood, and what he did on his pandemic-induced “vacation.” And he talks about music, too.

The Dukes Of Earle: Steve Earle with The Dukes (from left), Ricky Ray Jackson, Jeff Hill, Brad Pemberton, Earle, Chris Masterson, Eleanor Whitmore. Photo by Jacob Blickenstaff

Pollstar: You’re a troubadour in the truest sense of the word. What was it like to have to shut her down for two years?
Steve Earle: Well, it was hard, because [performing] is income, for one thing. The tour cycle before, I had cut my touring down to three months a year. That wasn’t because I wanted to, it was because it was just the only way I was going to keep my little boy in school. But the school he’s in, and has been in since he was 3, is in New York, and his mom didn’t want to stay in New York. So, to keep him there, the compromise we reached was I came off the road for nine months of the year and I only tour in the summer. And I needed to be in New York a little bit more to concentrate on theater music anyway, if that is what I want to do. We had just started that [prior to the pandemic], so my income was a little short for the year before that. And I was in an off-Broadway play that I’d written music for, but I was in as a performer, which is a cut in pay for me. So, we opened the play on March 3, 2020, and got shut down on the 20th. We had a tour booked, and I was going to come off stage from that play and then get on a bus and go make some money, and it didn’t happen. I got loans. Not everybody did. I found out a lot of people in the music business didn’t take advantage of those loans. I don’t know what that was about.

Like the PPP loans?
Yeah. Why would somebody not do that?

Probably the way it looked, the perception of it, maybe.
Perception of what? I know people that did [take the federal pandemic loans], and they’re big acts and people that would surprise you, people that could have afforded to come out of pocket and pay their guys, but they didn’t.

Well, their accountants probably advised that. Big bands, too.
Yeah, really big bands. A lot of people didn’t do it. I did it, I had to have the loan , and I used every dime, I didn’t keep a dime. I know other people that got loans for imaginary employees and shit, and that’s people in the business. I went and got the loans, and I got my guys through, I kept everybody on for the whole time that we were off, and we managed to get out and work two months last year. We had three months booked, but, like a lot of people, the June dates started to go away, because people were still scared. And so, we started July 2nd or 3rd or something last year.

There are a lot of artists that exist solely from what they can generate on the road.
I did; insofar as I don’t make any money from records, I need to tour.

The other part of that is, you’re a performer, man.
That’s what I do, there’s no doubt about that. I’m a singer/songwriter. This is the last of a set of records that once Jerry Jeff passed away, I had to do it. Because those were the three guys, Townes [Van Zandt], Guy Clark, and Jerry Jeff, guys I was in the room with. These three guys are always connected for me. They knew each other, they played the same folk circuit gigs, and “Mr. Bojangles” was written in Townes’ and [Van Zandt’s then wife] Fran’s apartment in Houston, which was above Sand Mountain (the legendary folk venue), above that coffee house there.

You were in the thick of it.
Well, I was later. I came along after the fact. That was archeology for me. I ran away from home when I was 14 and went to Houston. That’s the first time I was in Sand Mountain. That was in ’69, so the trail was pretty fresh then. Then I came back to live in ‘72, when I was 17, and played Sand Mountain all the time, and I interrogated anybody that was around. I knew Townes by that time. So when I got to Nashville, when I was 19, knowing Townes gave me an automatic introduction to Guy, so when Jerry Jeff, who was a very big star in that scene but by that time had moved to Texas, and those two records that he made after he moved to Texas, the MCA records, made him a large theater and arena act in about three or four states in the Southwest. In Texas, Oklahoma, New Mexico, Colorado.

Viva Terlingua [1973] would be one of those records, right?
The first one was Jerry Jeff Walker [1972], before Viva Terlingua. And then Walker’s Collectibles [1974] which is like, it’s got some great songs on it, but he carried the “not recording in studios” and “not having anybody to oversee” [approach] a little bit too far by Walker’s Collectibles, and it shows. But there’s great songs on Walker’s Collectibles. There was a great Billy Callery song called “The First Showboat,” he’s just incredible on that song.

For my Jerry Jeff album, I was determined this was going to be songs of Jerry Jeff’s that he wrote. And when you write one song like “Mr. Bojangles,” there is a tendency for that to overshadow everything else you did, and he wrote a lot of great songs.

I almost don’t even associate that song with Jerry Jeff as much as I do the stuff that came after it.
What do you mean?

Well, [Mr. Bojangles] was a huge radio hit for Nitty Gritty Dirt Band, and [Walker] never really seemed to ride on that song’s reputation that much, or so it seemed. And his songs that came after seem different, to me.
But see, I’ve known about him longer than you have. I found out about Jerry Jeff Walker when Jerry Jeff Walker came out, his first record, which was on ATCO, and it had that song on it. My drama teacher (Vernon Carroll) gave it to me in high school in 1969, because he wanted me to sing it in a play. That was also the same guy that gave me my first copy of The Freewheelin’ Bob Dylan. He was a big deal in my life, and theater was always a big deal because of him. And so I sang that song. That was the second song I ever sang in front of an audience of more than two or three girls that I was trying to impress at a slumber party. I was the guy that they let in the window at the slumber party.

As the story goes, you just went on a quest to go meet your musical heroes.
I crashed Jerry Jeff’s, I guess it was his 32nd, birthday party because I heard that he was going to play Castle Creek [in Austin, Texas], and I quit a job, hitchhiked to Austin, and I overheard [Walker’s band member] John Inmon telling a girl where the party was. So I lied to a girl I’d met, because she had a car and I’d hitched there, so I didn’t have a car, and I didn’t know Austin very well. And I said we were invited, so we went. I just stayed close to the wall, kept my hat down over my eyes to make sure nobody noticed I wasn’t supposed to be there. Not only was Jerry Jeff there, but B.W. Stevenson was there, Rusty Wier was there, Milton Carroll was there. Bill Callery – Billy C – who wrote “The First Showboat,” but also wrote “Hands on the Wheel.” He was a great fucking songwriter that was around. Have you ever seen “Heartworn Highways?”

Young’uns: Steve Earle and Guy Clark appear together on “Heartworn Highways,” a 1981 documentary by James Szalapski that captured some of the Outlaw Country founders in Texas and Tennessee in late 1975 and early 1976. Jim Szalapski / Courtesy of Light In The Attic Records

I was just about to bring it up, that you were in it.
Yeah. That was a couple years after that, I’m in Nashville, I’m almost 20 by that time. But if you look at that table [in a “Heartworn Highways” scene] and there’s stills of it too, it’s at Guy’s and Susanna’s house on Christmas Eve, 1975. And it’s Guy, Susanna, Rodney [Crowell], me, Richard Dobson, Steve Young, and Billy C in that circle around that table.

“Heartworn Highways,” it’s weird and disjointed, but, man, it’s just highly entertaining, the artists are incredible.
All those people, I had good teachers. I was around a lot of stuff that was going on, and it was on purpose. I followed these people around. I fucking stalked them.

But why did they let you? A lot of people are fans of artists, but they don’t take off chasing them and wind up in their inner circle.
It was just different then. I was just a kid, and people were willing to take me in. How do you think Bob Weir ended up in The Grateful Dead? Bobby was 16 when he met those guys, they were all older than him.

You also were obviously talented. Whenever you played something for them, they probably encouraged you, right?
Well, yeah, they absolutely did. And Guy championed me. There’s a point in “Heartworn Highways” where I’m playing a song, and he turns to the camera. He says, “Listen to this song.” And he did that with me, Rodney, everybody else. I was lucky to be there. But I’d met Jerry Jeff. I was in the same room with him several times in Texas, but once I became part of Guy’s circle, then Jerry Jeff noticed me. Then I left Guy’s band. We opened for Jerry Jeff several times when I was in the band, and then Guy came over one night and said, “Well, you’ve got a publishing deal now. You need to sit here and write some songs, and I need a better bass player. So I’m going to hire Charlie.”

And he hired another bass player. And so from that point on, Guy would be out touring, and sometimes Jerry Jeff would come to town, and he would call me because he had some trepidation about driving in Tennessee. Something had happened, I never knew exactly what, but he did not like to drive in Nashville. So he’d come and get me. One night he came and got me in the middle of the night and my poor first wife. I’d just go, and I’d disappear for a couple of days sometimes, but Jerry Jeff Walker called. He said, “Come on, that song you played me, ‘Illegal Cargo.’” I said, “Yeah, that’s a Dave Olney song.” He said, “I want you to play that song for Neil.”

I had no idea who Neil was. We got to the Spence Manor, turned out it was Neil Young. He didn’t want me to play one of my songs, he wanted me to play a David Olney song called “Illegal Cargo,” because he knew that I knew it because I had turned him on to it. We were all sitting around at Jim McGuire’s place, just playing songs and, eventually, I played the song for him and then I went and got Olney and drug him over there. And Olney didn’t like that; Olney was trying his best not to succeed. So he didn’t want anybody successful to know he was any good, he was one of those guys. There’s some people that are like that, and he was one of them. It hurt my feelings, but I love David Olney, so I did it, and I got to meet Neil Young.

As prolific a songwriter as you are, and there’s a finite number of records you can release in a lifetime, that’s a big dedication to do three records of covers, four if you count the JT record.
I know. And I need to make a record of my own songs. I’m writing songs, but what I’m writing right now is a musical of “Tender Mercies” with Daisy Foote, [author] Horton’s daughter. That’s going to take us a couple more years. So I’m going to start thinking about another record of my songs. I’ve written a few other things just as part of projects, I don’t even really want to get into it right now, but it’ll be a little bit different. Whenever I say I’m going to make this kind of record, that kind of record, it still just kind of turns out to be a Steve Earle record. Sometimes my records are about a concept in storytelling, outside of the music itself. The bluegrass record [The Mountain, 1999, with Del McCoury Band] I made just because I wanted to make the bluegrass record. I wanted to raise the bar and walk that tightrope, and it was a hard thing to do. The hardest thing I’ve ever done, musically, and I learned more making that record than any other record I’ve ever made.

Then there’s the blues record [Terraplane, 2015], which I believe was the last time we talked.
The blues record came a little more naturally, because it was such a big part of what I did for a long time. I saw Mance Lipscomb and Lightnin’ Hopkins in the same room at the same time. We get that in our DNA where I came from. I mean, country music and blues have always been intertwined, but it’s like, it’s segregation. It’s like people, Black people, white people borrowed from each other’s cultures, and then both sides like, “Okay, we did that, now let’s push it apart.”

A Second Helping: Steve Earle (right) did play with Neil Young again, but didn’t only play David Olney songs. Here, the duo played during the third Light Up the Blues Concert to benefit Autism Speaks at the Pantages Theatre on April 25, 2015 in Hollywood. Photo by Tommaso Boddi / WireImage

Why did it happen so drastically in the ‘60s and ‘70s? There was that moment where there were all these integrated bands. There was the Allman Brothers and the Chambers Brothers and Sly & the Family Stone, and Jimi Hendrix Experience. I was just talking about that, what happened to that? Why did music get segregated like that? And Steve Cropper was sitting there, and he looked at me like I was an idiot.

He said, “Because Dr. King got killed, and he got killed in Memphis, man.” And [Cropper] was in Booker T & the MGs when that happened. And that never happened again. They quit playing with each other, it put the last nail in Stax’s coffin. Dr. King got killed, and he got killed in Memphis. That’s what did it. He said that, and I don’t think it’s an oversimplification, I think it’s the truth.

I hadn’t thought about it, but it makes a lot of sense, because it’s sort of this defining line of demarcation, right?
Yeah. It’s right there. Right there, 1968.

When you’re talking about your genre-based records, what about a stone steel guitar-drenched Steve Earle country record?
Well, here’s the deal. I don’t want to be a Civil War re-enactor. So I’m thinking about making a country record. But the point is, I’m writing “Tender Mercies,” and you remember the movie?

Hell, yes.
Okay. Well, Mac [Sledge, the protagonist of “Tender Mercies,” a declining country music star], I know how to write Mac songs, but do you remember the band that was in it that kind of idolized him that came to see him at the gas station? They’re a much bigger deal in this thing that Daisy and I are writing. Because it’s a musical, so there has to be more opportunities for there to be songs. So the dance hall’s a much bigger thing and much more happens there, and the church is a bigger thing, and much more happens there, because there’s two places where you can sing and dance, even though they have to say you’re not supposed to. And we changed the church a little bit, and we moved it into now instead of the ‘80s, and we made the church a kind of hippieish, non-denominational mixed-race church, but then the minister’s Mexican-American.

Rosa Lee, the widow [character], is Hispanic. The widow. And part of it was producers saying, “Well, we got to have diversity for Broadway now.” And I liked doing that. Normally, I think, goddamn, it becomes math at that point, and politics. And that always rubs me the wrong way, but I understand why they’re doing it. But in this particular case, it’s interesting to me, narratively, to make her Hispanic and especially we moved it a little bit later in time.

Because it’s set in Texas?
Because it’s occupied Mexico. It’s part of the history of it, so it absolutely is. Where I grew up.

Well, they fought a war over it.
We won’t even get into it. That’s what my novel’s about that I’ve been working on forever. You know why Santa Anna attacked Texas?

I’ve read all that history.
It wasn’t what we were taught. He attacked them because they had agreed… those settlers that were developing those land grants and growing cotton, is what they were doing more than anything else, especially East Texas, that’s where the money was. It was all coming from East Texas, where something would grow out the ground. San Antonio, nothing grew around there in those days, because there was no irrigation at that point. But they had agreed to convert to Catholicism because it was a Catholic country, and they had agreed to not hold slaves, and they kept bringing slaves in and working cotton with them. And so, Santa Anna put an army together and attacked them to enforce that part of the law.

Never heard that.
It’s the truth. We’re not taught that because it’s part of this … The reason we keep tripping over race is that happened, and a decision was made by powerful people, “We’re not going to teach this, this is not going to be our legacy. We’re not going to tell this truth about ourselves.” And that’s what we keep doing, because we don’t want to admit that, number one, we came here and wiped out people that were already here, but that we just did whatever we wanted to. We took the land, we took Mexico, we took as much of it as we wanted, where the arable land stops, we stopped, and let them have the rest of it. And that’s just who we are. We’re kind of bullies.

Steve Earle with his son, the late Justin Townes Earle, to whom Steve Earle paid tribute on his 2021 album, JT. Courtesy New West Recomy Records

Well, that’s who “Man” is. That’s happened forever.
That’s true. But the point is, that’s not how we portrayed ourselves to be, and that’s not how we taught ourselves that we are. And I guess that’s what everybody does. But I was raised not to accept that. I’m kind of an old hippie, and I was raised to question these things and I did.

So we got to get some music stuff in.
Yeah, yeah, yeah.

I could talk all day about whatever you want to talk about, but I know we both got to move on. Music, did you miss performing, getting in front of people?
Yeah. When we’d been locked down for a year, I went to [live in] Tennessee first, and because it seemed like a safer place to be. I took [son] John Henry, and I was there at the house in Fairview. I started working out a lot and getting in the pool with him every day, and doing those guitar videos that I did and writing some. I wrote quite a bit, actually, but I started having the same problems a lot of people did. Everybody started to have mental health problems at the end of this [shutdown].

And for me, the biggest thing missing was I don’t even know how to validate what I do without going out and playing it for an audience. That’s just how I do it. I needed it really badly.

And so we did finally get out last summer for the first time. It was a blast, we had a lot of fun. We lost our steel player, he tested positive and had to get left behind about two-thirds of the way through the tour; that was a bummer. But other than that, we got through it relatively unscathed.

Did you do the bubble and all of that?
Yeah. We’re still kind of doing it now.

I’m breaking your bubble. Hate to burst your bubble.
Yeah. Are you vaccinated?

Okay. You’re supposed to be. We’re okay with being around anybody that’s vaccinated. We don’t let anyone on the bus, just because that’s so close that we just… I don’t even let my girlfriends on the bus for the last couple tours. But we got a couple of fresh COVID cases because Chris and El got back from Europe on their own tour like three weeks ago, and both tested positive immediately. John Henry and I finally got it, we tested positive flying home from the Bahamas on January 1st. And I’m triple vaxxed.

So you got more dates in than you even would have hoped last year, right?
Yeah. And I think we’re going to get the whole tour in this time. We’ll decide what’s going to happen if anybody tests positive. Because there’s work at stake, we’re trying to keep going, and we decide what to do just to keep from having to make that decision. We’re just trying to keep the chances of that to a minimum.

With your vast catalog and new records of somebody else’s songs, how do you put a set list together?
It’s hard. Twenty-two albums, and only four of them have not been my songs. It’s really hard. We tried to just put a few things in that we haven’t played in a long time this year. We were limited on time, because like I said, this tour manager threw us a curve ball and quit seven weeks out. So we were scrambling trying to cover other things. I ended up just putting about three or four things that we didn’t play last year into my songs on the set.

We front loaded [the Jerry Jeff songs]. Last time, there wasn’t supposed to be a [“Ghost of West Virginia Tour” and then the “JT Tour” [JT was Earle’s tribute to his late son Justin Townes Earle, who died Aug. 20, 2020, of an accidental overdose]. And I’m glad I didn’t have to go through that. As it is, we’re going to do a concert of Justin’s songs, still. We had it scheduled for the last January 4th, which would’ve been his 40th birthday. It’s going on at the Ryman Auditorium, and I’m pretty sure it’ll happen this year.

But we did do four songs from [2020 album] Ghosts of West Virginia, and then four songs from JT in this last year. But it was largely my stuff … We’d been away for a long time, and we wanted to give people what they want. This one’s kind of designed the same way. We start with the Jerry Jeff stuff and play all that right in the front of the show. And then we go on to play my stuff, and that’s what we do. I’ve only played this [set] in front of an audience of friends and family last night before we left. So I won’t know whether this is it until tonight, but I might keep it. Usually, I’ve done a pretty good job up to this point. We may find something where we logistically have to move something or drop something or add something because of something we overlooked in rehearsals. But barring that, we won’t change it much after tonight.

e.willie 1
On The Road Again, Thankfully: Steve Earle performs during the “To Willie: A Birthday Celebration” concert at Luck Ranch on May 1, 2022, in Spicewood, Texas.
Photo by Gary Miller / WireImage

When you say keep it, you mean the whole set list?
Yeah. I don’t change them very often. I got a small crew, a guitar tech that has to take care of me and Chris. Since he has to take care of both of us, he would kill himself if I change the show very much, just because it gets hard for him to prepare if he doesn’t know what’s coming every night.

A lot of artists with lengthy touring careers have certain songs that they simply must play every night to keep fans happy. Do you?
I play “Copperhead Road” every night. I play “Guitar Town” every night. I didn’t play “My Old Friend the Blues” last year, and I’m not playing it this year. I might bust it off in an encore. I almost dropped “Someday.”We dropped “Someday” a couple of years ago, but we got so much feedback about it not being there. I’m not on social media, so stuff comes to me slow. I hear it from other people, because everybody else on the bus is. I don’t read reviews.

Did you read the last story I wrote on you?
I don’t read anything.

Oh, come on.
Just one of those things. I just don’t do it.

I was the guy who gave The Hard Way the good review.
Yeah, right (laughs). I don’t know, what’s funny about that record, I read reviews back then. I don’t even remember that getting terrible reviews. I just think it got ignored a lot, more than anything else, because MCA just started to kind of pretend that it didn’t exist. And that record was… That record’s hard for me to listen to. Not because I’m ashamed of it, because it’s a very dark period in my life, and that’s what it’s about. I’m about to slip off the face of the earth, and I know it.

Dark record, but it’s powerful. I like it. So, tonight’s the first night of the tour.

Decatur, Alabama.
Yeah. We have a history of playing someplace fairly close [to Nashville] the first night. Decatur’s a good place. This theater exists here. The audience up and down here. I don’t know how tickets are going to do, but we did this about halfway through the trail last time. We were here in 2019.

In this room?
Yeah. Yeah. And it’s kind of a mom-and-pop room. It’s locally run, I think it’s a not-for-profit, actually, but they do good stuff here. A lot of people I know are playing here this summer.

Are you excited about getting out on the road?
Yeah. Yeah. I am. And then we’ll play tonight. We got a day off to kind of think about it tomorrow. And then we’re in Nashville, Indiana. It’s like a performing arts center there. Brown County, I think it’s called. And I’ll see Larry Crane, who I haven’t seen in a while and he’ll be there and just, he’s still in Indiana. He was in Florida for a few years, but he ends up back in fucking Seymour. And then we go to Jergel’s Rhythm Grille, which is Warrendale, Pa. That whole audience will be from West Virginia, West Virginia panhandle, because it’s right there.

Thunder and Copperhead Road: Steve Earle and Brue Springsteen backstage at New York City’s Town Hall in Dec. 2021. The duo peformed together for the annual John Henry’s Friends benefit, organized by Earle and City Winery, with proceeds going to NYC’s Keswell School to helps kids with autism. Photo by Danny Clinch

You look ready to play. I can’t wait to see it. At this point, I’ve been interviewing you since ‘87 and you were hard charging, and everything was ahead of you. And now, look at where it’s ended up; how do you feel about your legacy and what do you still want to do?
What I want to do, I want a hit Broadway show before I die. I started [Broadway work] when I was essentially 50, it takes a while. I was very careful about being accepted in the theater community, because it’s not lost on them the record business didn’t give a fuck about them. Now everybody comes like rats from a sinking ship, because our business vanished. And it’s like the last place there’s any real mailbox money for songwriters is Broadway. And so I want to do that, and I want to do it because I can make money.

And I’m just trying to set things up for John Henry for after I’m gone. That’s the ambition. That’s what drives me in the morning. And I sold all my IP [intellectual property]. I did what Bob [Dylan] and Bruce [Springsteen] did up to now. I’m starting all over with a clean slate, but I’m starting with no debts. And I own a place in New York, which I’ve been renting the whole time I’ve been there, 18 years. So I’m not throwing that money away anymore.

Why would anybody that does something that they love retire? I don’t think of it as the end of anything. I’m going to work as long as I’m capable, and hopefully that’ll be until the second that I cash in. I work every day, man. I wake up and write something every morning.

Even when I’ve got John Henry, I get up at 6 a.m., I hit the yoga mat, then I try to get as
much done as possible before he gets up. I usually, depending on what he’s having
for breakfast, because I don’t usually eat it, get his breakfast going and pretty much
set up. And then if he’s still asleep, especially, I’ll sit down and I’ll start writing. And when
he gets up, I’ll get him fed. I mean, I get his food in front of him, and then I’ll keep working. And whatever I’m working for, right until we go out the door at 8:30. Then I’ve got that banging around in my head. I drop him off to school. I walk the four miles back down to my apartment and write on my phone. And it’s all on my computer when I get back.

I’ve been working. Right lately, it’s been a little crazy, and at first I thought this was insane, I’ll never get anything done, but I’ve literally been working a little bit of time on
the novel, a little bit of time on this one song that I was trying to finish for “Tender Mercies” that I started in the Bahamas when we were quarantined, and I’m painting a little bit,

We’re all going from Dallas to Marfa (Texas) on what would’ve been our day off before [Willie Nelson’s] 4th of July picnic; we’ll go to Marfa, play a private show for Terry and Jo Harvey Allen’s 60th anniversary. A lot of people are coming in for this. We’re going to go do that, and then head back to Austin for the picnic. I was in Austin for Willie’s birthday. He’s 89, man.

What about this part of it, getting on the bus, and that kind of life, rolling all the time. Do you like that?
I love buses. I miss John Henry a lot when I’m gone, because the thing about him is kids with autism as profound as his, like in traffic and stuff in New York, you keep a hand on him pretty much all the time, so you’re really connected in a way that you normally aren’t to a kid at 12 years old. And so when he goes to Allison [Moorer, ex-wife and mother to John Henry], I’m exhausted, “Here, take this little f…er.” And then an hour later, I feel amputated and I don’t know what to do.

When you look back at these records from Guitar Town on, is there pride there?

Yeah. I’ve never made a record I’m ashamed of.

I’ll let you do your sound check. Anything you want people to know?
We’re going to be out every summer. We’re going to do a few things here and there. There’s a chance we’ll go to Australia at Easter, we’re talking about that. But we’ll definitely be out again next summer. We’re going to do Hardly Strictly Bluegrass in October, like we always do. And John Henry’s getting old enough now, and I developed a little bit of childcare that I trust to keep him for a weekend, so I might start running out playing some solo shows during the wintertime, that I can reach by airplane and go and do one or two shows here and there.