Of course Jeff Tweedy—so-called “alternative country” pioneer in Uncle Tupelo, and the leader of one of the nation’s most enduring and experimental rock bands in Wilco—is a fan of Terry Allen, the Lubbock-born not-exactly-country songwriter and one of America’s most enduring and experimental multimedia artists. But it was still a surprise on New Year’s Eve 2020, when Tweedy and his youngest son Sammy covered “Death of the Last Stripper,” a song from Allen’s album Just Like Moby Dick, on their pandemic-born Instagram Live show. A few months later, when the Tweedys took a road trip on the Wilco tour bus that eventually brought them into Amarillo, that inevitably led to a rendition of Allen’s “Amarillo Highway.”

Way back in 1994, Tweedy worked with longtime Allen collaborator and fellow Lubbock legend Lloyd Maines on the Uncle Tupelo album Anodyne. But it was only over the past year that Tweedy and Allen got to work together. First, Allen was part of Wilco’s induction into the Austin City Limits TV show Hall of Fame, contributing a solo piano version of Tweedy’s epic ballad “One Sunday Morning (Song for Jane Smiley’s Boyfriend).” And then Wilco invited Allen to perform at the Solid Sound Festival, which was held over Memorial Day weekend at the Massachusetts Museum of Contemporary Art.

For Allen, Solid Sound capped off a half year that has already included his “MemWars” exhibit at the Blanton Museum of Art in Austin, an ACL episode of his own, and the latest in a series of album reissues from his label Paradise of Bachelors. For Tweedy, the festival also served as the launch of Wilco’s twelfth studio album, Cruel Country, a title that plays on both the musical genre and the current state of the U.S.

Though they are a generation apart and of different backgrounds, the 54-year-old Tweedy and the 79-year-old Allen share musical influences, a certain artistic restlessness, and a fastidious devotion to their craft. They are also both creative types beyond music, experimenting with visual art, books, and poetry. Shortly before Solid Sound, Texas Monthly spoke to the two artists via Zoom—Allen was in in New Mexico, Tweedy outside of Chicago—about their unique connection.

Texas Monthly: Jeff, how did you first come to Terry’s music?

Jeff Tweedy: Man, I don’t even know how it happened.

Terry Allen: I could say the exact same thing!

JT: I worked in a record store from my teen years on, and Terry’s just one of those secrets that gets handed down from your fellow employees. It must have been the nineties when I first started hearing Terry’s music, and it just feels like it’s always been there for me. Those records have a real life. They find the people that need ’em.

TM: And, Terry, have you had a relationship with Wilco’s music over the years?

TA: I haven’t, up until really recently. I’ve always known and admired the band. Then at the Austin City Limits [Hall of Fame] show I did “One Sunday Morning.” It was a very difficult song for me to do, but every time I played it, and the more I worked on it, the more incredible that song was to me. An extraordinary poem that Jeff stuck me with! I was worried about doing it, but I loved the song and the ideas that were in the song.

Since then, I’ve tried to acquaint myself with as much Wilco as I can. This morning, I listened to the new record. And I think it’s an extraordinary record.

JT: Oh, thank you.

TA: I just really admired it. My favorite thing about any record that I hear is something that makes me want to work—whether it’s make a song or make a picture. I don’t think you can compliment anything any more.

JT: That’s what I’m always looking for. I want to listen to stuff and read things and find something that makes me just reenergized. To aim for that bar. I’ve always said I listen to records until I can’t take it anymore and have to make something. I can’t let the challenge go unmet.

TA: I remember when Tower Records was supreme, and you would get a new album, and the first thing you did was read all of the liner notes, put it on the record player and play every song. It was an event for the whole house. And I felt that way about [Cruel Country]. I wanted to sit down and listen to it over and over, because I’d get sidetracked going off from all these different directions listening to certain songs. And I think that’s what music does. It takes you to other places.

I was listening today to that song, what is it, “the bird at the back of your head?”

JT: “A Bird Without a Tail (At the Base of my Skull).”

TA: Yeah. And I totally got lost in it, because it reminded me of my mother. She had these painted porcelain plates of scenes with birds hung all the way around the dining room. And there was a fire in her house that burned most of the house. But these plates were still intact. And I got on a ladder and reached up to get them down and they just crumbled. Disappeared.

JT: The poem in that song is from the sixteenth century,  and it’s anonymous. It felt like such a mysterious and weird poem from such a long time ago. So that’s a song that started from me trying to imagine what music would go with that poem. One of the things music has gotten away from in a lot of ways is the representational idea of music itself being able to conjure images.

Y’know, one of the things that I hadn’t really heard of Terry’s that really inspired me a lot in the last few years is the reissues that Paradise of Bachelor did of, for lack of a better word, his radio plays [Pedal Steal + Four Corners and Bloodlines]. I mean, do you consider ’em plays Terry?

TA: I consider them radio shows. Just stories.

JT: It’s some of the most inventive and inspiring stuff I’ve ever heard in my life. [You] use everything at your disposal to get a story across. It shatters the idea of a record being a certain length, and incorporates spoken word and sound design. I don’t know of any storytelling that really hits me like those records. I can listen to ’em forever.

TM: Jeff, in your book How to Write One Song, you talk about how you like to cover songs not just because you like them but because it teaches you something about songwriting. What was it like to do Terry’s “Death of the Last Stripper?”

JT: Well, any song like that, it just reminds me to really try to be precise with language. That song has a simplicity to it. It’s so clear in its language, the meter is all right, and it’s sung effortlessly. That doesn’t just happen. That’s something that somebody really crafts and works on. So when I sing a song like that, it inspires me to take the extra time to try and get my language to be as clear and crystalline.

TA: I haven’t heard you sing that song. I’ve got to hear your version.

TM: You are both big believers that you have to sit down and do the work, not just wait for inspiration to come, yes?

JT: I am. I think I barely would have written three songs in my life if I just waited around for them to happen.

TA: Yeah, same thing. It’s really about just doing it. If you wait for a muse you’re gonna be buried in the ground before he shows up

JT: If I get myself in the position where I have a guitar, or I have a pencil, and I just start, after years and years of doing it I have a certain amount of faith that something’s going to happen that I didn’t expect. I discover myself. Or I discover something. It’s an unfolding of moments, into something that you couldn’t have sat down and intended to do.

TA: Yeah, I go to my studio every day. Even if I really don’t want to. It’s that Flannery O’Connor thing of spending three hours every day in front of her typewriter. Even if nothing happened, she wants to be there in case something does happen.

JT: I think that the whole process, my whole life, has been just getting more and more comfortable with not knowing.

TA: Yeah. I think all artists, the thing they have in common is that they really like being insecure.

JT: (laughs) We’re just trying to work our way back to being babies.

TA: Secretly really love it.

JT: Divine discontent.

TM: You’ve each raised two sons who have their own artistic lives, and also collaborate with you. How were you able to create the space for them to become themselves but also share so much?

JT: I just don’t believe in parenting as being that important, to be honest. I think every parent is good enough. Obviously you give them love and shelter, but as far as steering them, my wife and I haven’t done a whole lot of it, other than just finding out what they’re interested in and supporting it. I think that they have just been around so much art and music that it looked like a normal thing to do, so they both gravitated towards it. And as far as getting to play music with my family, I don’t know how I got so lucky. It’s just one of the coolest things ever.

TA: I feel exactly the same way. We never pushed them to do anything. But they were around so many people that make things, and do things. I think it was kind of osmosis. People ask me, “What do your sons do?” and I say “Well, one’s an artist, one’s a musician. So it’s a double f—up!” No lawyers, no doctors, no accountants, none of that stuff that that you quote-unquote need. But the satisfaction of playing music with your kids and doing things with your kids, it’s one of the joys of my whole life.

JT: The whole experience of looking over onstage and seeing my sons standing there singing with me . . . I mean, I’d be happy if they just hung out with me as much as they do! But playing music is such an intimate thing. Nothing compares to that level of trust you have with your children, and the musical relationship really brings it out.

TA: It’s huge, to be onstage and turn around to see them playing. It takes all of the edges off. Well, not all of them. But most of them.

TM: Terry, I think every article written about you has always mentioned the quote where you said, “People tell me it’s country music and I ask, ‘Which country?’” That thought seems germane to the title of this Wilco record.

TA: Those labels, a lot of times I think they’re used simply to allow people not to have to think. They can just call it something and move on. I read what [Jeff] wrote about the record and thought it was spot-on. You make music. You don’t make country music or whatever other kind of music. You make music that you hope is true. You can call it whatever you want to, but it’s still going to be whatever it is.

TM: Well, Terry alluded to the notes or, really, press release you wrote for Cruel Country, in which you joke “Wilco goes Country! Is that something people still say?” and circle around the idea of whether we should really consider this a country record or not.

JT: I thought it would be important to explain a little bit about how the band came to just go ahead and call it a country record. We might as well call it a country record, because it’s a country record to us.

The idea of using a genre idea, or a shape, was really helpful as a band coming together to make music again after the pandemic. We had to reestablish ourselves in some common territory. Maybe that’s the country that we built up around ourselves. But it was much easier to wrap our heads around [country music as] an understandable shape, like a rectangle. Something primary to our musical experience. And then projecting into that whatever distortions and confusion that is happening around us, as opposed to moving heaven and earth to try and find a new shape.

TA: I really liked [the record] because it didn’t focus, to me, on any of those clichéd images or ideas. But it’s about the land, like [Cruel Country’s final track] “The Plains.” But I would never listen to that record and think it’s country music, unless I read what you wrote. I think all of the parallels that you brought up with democracy and just kind of the state of this country and the state of the world—the hell zone that we’re in—that was an amazing tone.

JT: I always say I hate music that’s trying to sound like itself. And a lot of music, if it’s centered around a genre, you have to have the trope that signals to everyone, “this is what kind of music it is.” But to me, the people that wrote the songs that “country music” is founded on, they had no genre. There was nothing to indicate to them that what they were doing was acceptable or not acceptable. The idea that there’s a certain type of music called bluegrass, that’s an agreed-upon fiction. That’s not how the original music was made. And it shouldn’t be how anybody approaches art.

But it’s a way to approach commerce, for sure. And we live in a world where  that’s a part of it. But for the artist, I don’t know how that helps you.

TA: I don’t think it does. I think it’s totally fabricated into some kind of mythology to make money. You make something, you put it out there, and then it becomes subject to all of that twisting and turning. But it’s still what it is. It doesn’t matter what any critic says, it doesn’t matter what any publicist says. It’s so much what it is that it basically says, “I am who I am. F— you.”

JT: A tiny, courageous act of self-liberation.

TA: Destined to obscurity.

This interview has been condensed and edited.