Two years ago, singer-songwriters Bonnie “Prince” Billy and Bill Callahan released a cover of Yusuf/Cat Stevens’ “Blackness of the Night”, a dark and quiet song about exile, grief and loneliness. Musician Azita Youssefi, who records as AZITA, contributed acoustic guitar and synthesizer, giving the track a surreal swing. The timing of the song’s arrival — weeks before the presidential election, months before the rat race for vaccine appointments — felt like a strange little gift. Life seemed bleak, but connection and collaboration were still possible. Bonnie “Prince” Billy, the pen name of Will Oldham, and Callahan, who began his career as Smog, are natural musical companions. Each has a rich, idiosyncratic voice (Oldham’s is lean and snappy; Callahan’s is low and reticent), and they’re both former representatives of Drag City, the Chicago-based independent label founded in 1990 by Dan Koretzky and Dan Osborn. The label has hosted, at various times and for varying durations, artists such as Pavement, Joanna Newsom, Scott Walker, Stereolab, Silver Jews, Death and the comedian John Mulaney. For over thirty years, Drag City has provided something of an eccentric haven for artists working outside the mainstream, sometimes far away. Until recently, it was one of the only record labels to refuse streaming. (In 2017, he began selectively publishing his catalog on Spotify, Apple Music and Tidal.)
More covers followed from Oldham and Callahan, who were joined each time by another Drag City roster member: Hank Williams, Jr.’s “OD’d in Denver” (featuring Matt Sweeney), “Wish You Were” by Billie Eilish. Gay” (with Sean O’Hagan), “I Love You” by Jerry Jeff Walker (with David Pajo), “Lost in Love” by Air Supply (with Emmett Kelly) and “I’ve Been the One” by Lowell George (with Meg Baird). Some songs (“Deacon Blues” by Steely Dan) favor the original arrangement, while others (“Wish You Were Gay”) seem totally reinvented. Eventually, the nineteen covers the pair posted online were collected for “Blind Date Party.” I recently reached out to Oldham and Callahan via Zoom – Oldham from his home in Louisville, Kentucky, and Callahan from his home in Austin, Texas – and we talked about the shock of the pandemic, the future of independent labels and the mourning for David Berman.
It’s really nice to see you both.
Will Oldham: Bill, you look so good with glasses! I don’t remember if I’ve ever seen you wear them. You look very distinguished, like a 70s action star.
I was going to say “professional”.
WO: It’s like a Lee Marvin, Robert Redford, man against the universe, flamboyant kind of thing.
Bill Callahan: Thank you. I went through thirty pairs of glasses. I always break them, or my kids grab them and shock them. I think these are my glasses forever.
I listened to each of the “Blind Date Party” singles as they were released online, but found it to be a very different experience to hear them put together and sequenced.
WO: Bill came up with the sequence. I like the flow.
Bill, is this work – the order of the songs – instinctive for you?
BC: He is. It’s the one thing in music that I think I’m good at. And, you know, I proved it with this. [Laughs.] When I make my records, I’ve already sequenced them before even going to the studio. The songs may be unfinished, but they already have a sequence.
The act of serialization can be shockingly powerful – sometimes you put one thing next to another and then change them both. You started collaborating on these songs in the spring of 2020. How did you start?
WO: During the last year of his life, David Berman came up with the idea of a tour with Bill, David and myself called the Gentlemen of Drag City. We brainstormed casually, thinking that would probably never happen. But what if that do? How fun would that be? This does not happen. And then the lockdown happened. One day I was talking with Dan Koretzky. I throw ideas at him, and usually hear his glassy eyes on the phone. I started thinking about Willie [Nelson] and Wayne [Jennings] records, how they would team up – they were supposedly duet records, but maybe Waylon wouldn’t be on a song, or it wouldn’t be totally obvious, or they would be covering for each other. So I thought, Well, what if Bill and I did this, and tried to get as many other people together as possible? We still didn’t know what was going on in the world. How could we jam all these musicians and get them to do something together? Impossible! But everything happened. We started the engine, and it wouldn’t stop for months and months.
In the early panicked 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 – it’s time to reset. He meant intentionally. But, over the past couple of years, it’s often felt like someone pulled the emergency brake on music, or at least live music. How did each of you react to this?
BC: I always try to write. But one sentiment that I’ve heard a lot of people echo with me is that there’s nothing worth writing about except the pandemic, and what can you say about the pandemic? He took so long to show himself to us. I went through a period where I thought: There’s no place for my stupid little music in this world. When you do a cover, you are not responsible for the lyrics. It was the perfect way to keep working during a confusing time.
WO: I try to deal with this idea of the fallow period. I think I’ve always been comfortable with the times when there’s no writing, because why worry? It seems worrying about it would only make it a problem when it isn’t. You just have to trust that something is going on. Bonnie “Prince” Billy’s record “I Made a Place” had just come out, and I told Drag City that I was going to stick with my kind of skeletal, dark social media accounts, or shut them down for a while. , or , you know, get rid of them. And then, at that point, the pandemic happened, and I thought, Oh, well, that’s why Big Tech engineered the virus, right? To increase everyone’s addiction to these forums. And I thought, we’re going to cover these songs, but we’re going to do them on steroids, we’re going to use all the resources we have, 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 that we had some degree of connection with, superficial or strong, through Drag City. Rather than mourning the lack of connection with others, it was the perfect time to take stock of the connections we had.
It seems like a good time to ask you both about the title. It’s playful, but it also suggests a lack of context. I like to sometimes come to an artwork without much information. It’s something I love about collecting pre-war 78 rpm records – for all sorts of nefarious and not-so-negative reasons, it’s often hard to find information about pre-war American artists . So the song exists on its own terms, unhindered. There is something difficult about it, but also something beautiful. Did you encourage some of the artists you worked with to come to these songs blind, and not worry too much about provenance?
BC: A blind date comes to your door. It was like that with those songs. We gave these artists full permission to do whatever they wanted, absolutely whatever they wanted, on the cover. Make him unrecognizable, whatever. So when we retrieved those files, it was like a stranger showing up for a date.
WO: Bill said “Blind Date” and I said, how about “Blind Date Party”? Nobody chose his songs; each was randomly assigned a song.
Was anyone in Drag City pulling songs out of a hat?
BC: If we told you the truth, you would think that we were tearing your chain off. [Laughs.] He was chosen by a dog, Dan Koretzky’s dog. He set up an elaborate situation in his apartment, with each song title and each performer’s name on a treat. Somehow, the order in which the dog found the treats around Dan’s apartment determined who got which song.
WO: I like to think about what you just talked about – the mess, the quirks, the mystery behind some of the pre-war 78s. Bill and I both brought big names to the table, in my case Lou Reed, and in Bill Iggy Pop’s case. They are well recognized, well respected and well celebrated. And yet, I still don’t feel like the Lou Reed I love is recognized and celebrated. Maybe everyone feels that way about some of their favorite performers or artists. But, you know, I think “Legendary Hearts” is like a pre-war 78. It’s still one of the best records I’ve ever heard, and yet I’ve never seen anyone try to dissect it or tell me anything about it. And “Rooftop Garden” is even deeper. Just, like, what? Why is it a good song? I do not know. It’s 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 that? Where does this magic come from, and why does it move me? We think we know something about Iggy Pop, and luckily we don’t, because that way I can still listen to that Iggy Pop song and be completely transported to a place where the rules of reality don’t apply. not necessarily apply.