Two years ago, the singer-songwriters Bonnie “Prince” Billy and Bill Callahan released a cover of Yusuf/Cat Stevens’s “Blackness of the Night,” a grim, quiet song about exile, heartache, and loneliness. The musician Azita Youssefi, who records as AZITA, contributed acoustic guitar and synthesizer, giving the track a surreal wobble. The timing of the song’s arrival—weeks before the Presidential election, months before the frantic scramble for vaccine appointments—felt like a strange little gift. Life felt dark, but connection and collaboration were still possible. Bonnie “Prince” Billy, the nom de plume of Will Oldham, and Callahan, who began his career as Smog, are natural musical bedfellows. Each has a rich, idiosyncratic voice (Oldham’s is lean and brittle; Callahan’s is low and reluctant), and they are both erstwhile representatives of Drag City, the Chicago-based independent label founded, in 1990, by Dan Koretzky and Dan Osborn. The label has been home, at varying points and for varying lengths of time, to acts such as Pavement, Joanna Newsom, Scott Walker, Stereolab, Silver Jews, Death, and the comic John Mulaney. For more than thirty years, Drag City has provided a kind of oddball shelter for artists working outside the mainstream—sometimes far out. Until recently, it was one of the only record labels to refuse streaming. (In 2017, it began selectively releasing its catalogue to Spotify, Apple Music, and Tidal.)

More cover songs followed from Oldham and Callahan, who were joined each time by another member of the Drag City roster: Hank Williams, Jr.,’s “OD’d in Denver” (featuring Matt Sweeney), Billie Eilish’s “Wish You Were Gay” (featuring Sean O’Hagan), Jerry Jeff Walker’s “I Love You” (featuring David Pajo), Air Supply’s “Lost in Love” (featuring Emmett Kelly), and Lowell George’s “I’ve Been the One” (featuring Meg Baird). Some tracks (Steely Dan’s “Deacon Blues”) favor the original arrangement, while others (“Wish You Were Gay”) feel wholly reinvented. Eventually, all nineteen covers that the pair released online were collected for “Blind Date Party.” I recently connected with Oldham and Callahan via Zoom—Oldham from his home in Louisville, Kentucky, and Callahan from his home in Austin, Texas—and we spoke about the shock of the pandemic, the future of independent labels, and mourning David Berman.

It’s really nice to see you both.

Will Oldham: Bill, you look so good with glasses! I can’t remember if I’ve seen you wear them before. You look very distinguished, like a seventies action star.

I was going to say “professorial.”

W.O.: It’s like a Lee Marvin, Robert Redford, one-man-against-the-universe, guns-blazing kind of thing.

Bill Callahan: Thank you. I’ve gone through thirty pairs of glasses. I always break them, or my kids grab them and they wishbone. I think these are my forever glasses.

I listened to each of the singles on “Blind Date Party” as they were being released online, but I’ve found it’s a very different sort of experience hearing them collected and sequenced.

W.O.: Bill came up with the sequence. I love the flow.

Bill, is that work—the ordering of songs—instinctive for you?

B.C.: It is. It’s the only thing to do with making music that I think I’m good at. And, you know, I proved it with this. [Laughs.] When I’m making my records, I already have them sequenced before I even go in the studio. The songs might be unfinished, but they already have a sequence.

The act of serialization can be shockingly powerful—sometimes you put one thing next to another thing and subsequently change them both. You started collaborating on these songs in the spring of 2020. How did you begin?

W.O.: In the last year of his life, David Berman came up with this idea of a tour with Bill and David and myself called the Monsieurs of Drag City. We casually threw ideas back and forth, thinking it would probably never happen. But what if it did? How much fun would it be? It didn’t happen. And then the lockdown did happen. One day, I was talking with Dan Koretzky. I’ll throw ideas at him, and usually I can hear his eyes glaze over on the phone. I started thinking about Willie [Nelson] and Waylon [Jennings] records, how they would team up—these were supposedly duet records, but maybe Waylon wouldn’t be on a song, or he wouldn’t be totally evident, or they would cover each other. So I thought, Well, what if Bill and I did that, and tried to round up as many other people as possible? We still didn’t know what was going on in the world. How could we wrangle all these musicians and get them to do something together? Impossible! But everything happened. We started the engine, and it didn’t stop for months and months.

In the panicked early days of the pandemic, I thought a lot about an interview I read with Frank Sinatra, years ago, in which he said something about the importance of fallow periods for artists—time to reset. He meant in an intentional way. But, these past two years, it has often felt as if somebody pulled the emergency brake on music, or at least on live music. How has each of you reacted to that?

B.C.: I’m always trying to write. But a feeling that I’ve heard a lot of people echo back to me is that there’s nothing worth writing about, except the pandemic, and what can you say about the pandemic? It took such a long time to show itself to us. I went through a period of thinking, There’s no place for my tiny stupid music in this world.When you’re doing a cover, you’re not responsible for the lyrics. It was the perfect way to keep working during a confusing time.

W.O.: I’m trying to process this idea of the fallow period. I think I’ve always been comfortable with the times when there isn’t any writing happening, because why worry? It seems like worrying about it would only make it a problem when it isn’t a problem. You just have to trust that something’s going on. The Bonnie “Prince” Billy record “I Made a Place” had just come out, and I told Drag City that I was gonna stick with my kind of skeletal, shadowy social-media accounts, or close ’em down for a while, or, you know, get rid of them. And then, right then, the pandemic happened, and I thought, Oh, well, this is why Big Tech designed the virus, right? To up everybody’s dependency on these forums. And I thought, We’re gonna cover these songs, but we’re gonna do ’em on steroids, we’re gonna use all of the resources we have at our disposal, including social media. We identified and expanded our community through it. It was about Bill and I connecting with each other, and then connecting with all these different artists with whom we had some degree of connection, superficial or strong, through Drag City. Rather than grieve the lack of connection with other people, it was a great time to take stock of the connections that we did have.

This seems like the right time to ask you both about the title. It’s playful, but it also suggests a lack of context. I sometimes enjoy coming at a piece of art without a lot of information. It’s something I like about collecting prewar 78-r.p.m. records—for all sorts of nefarious and not-so-nefarious reasons, it’s often difficult to find out any information about prewar American artists. So the song exists on its own terms, unencumbered. There’s something challenging about that, but also something beautiful. Did you encourage some of the artists you worked with to come to these songs blind, and not to worry too much about provenance?

B.C.: A blind date shows up at your doorstep. That’s how it was with these songs. We gave full permission to these artists to just do whatever they wanted—absolutely anything they wanted—to the cover. Make it unrecognizable, whatever. So, when we would get these files back, it felt like a stranger showing up for a date.

W.O.: Bill said “Blind Date” and I said, how about “Blind Date Party”? Nobody chose their songs; everyone was assigned a random song.

Was someone at Drag City pulling songs out of a hat?

B.C.: If we told you the truth, you would think we were yanking your chain. [Laughs.] It was chosen by a dog—Dan Koretzky’s dog. He set up an elaborate situation in his apartment, with every song title and every performer’s name on a treat. Somehow the order in which the dog found the treats around Dan’s apartment determined who got what song.

That’s incredible.

W.O.: I like thinking about what you were just talking about—the mess, the vagaries, the mystery behind some of the prewar 78s. Bill and I both brought some big names to the table—in my case Lou Reed, and in Bill’s case Iggy Pop. They’re well recognized, well respected, and well celebrated. And yet, I still don’t feel that the Lou Reed I love is recognized and celebrated. Maybe everybody feels that about some of their favorite performers or artists. But, you know, I think that “Legendary Hearts” is like a prewar 78. It’s still one of the best records I’ve ever heard, and yet I’ve never seen anybody try to dissect it or tell me anything about it. And “Rooftop Garden” is even deeper. Just, like, what? Why is this a good song? I don’t know. It is a good song, but why is it a good song? It’s wild. Or “I Want to Go to the Beach,” by Iggy Pop. It’s, like, well, what’s up with this? Where did this magic come from, and why does it move me? We think we know something about Iggy Pop, and thankfully we don’t, because that way I can still listen to this Iggy Pop song and be completely transported to a place where the rules of reality don’t necessarily apply.