FEATURES Bill Callahan and Will Oldham Discuss Their Collaborative LP By Marc Masters · January 18, 2022

Bill Callahan and Will Oldham have released records on Chicago label Drag City for decades, and have known each other for nearly as long. But they’d never considered collaborating until they found themselves unable to leave their homes during COVID-19 lockdowns.

“We thought, ‘Everybody’s stuck—let’s brainstorm ways to potentially address it, get some survival-oriented activity happening,’” says Oldham, speaking via Zoom from Louisville, Kentucky. Callahan, chiming in from Austin, Texas, agrees. “I think Will wanted to give everyone a sense of purpose: the label, the musicians, the entire world,” he says. “Here was an opportunity to actually do it.”

After Oldham mentioned the idea to Drag City’s Dan Koretzky, a plan quickly emerged: Oldham and Callahan would each choose nine songs to cover: three that each wanted the other to sing lead on, three they would sing lead on themselves, and three they could share as a duet. Kortetzky received their master list, then randomly assigned a Drag City artist to create the music for each pick. Those instrumentals were sent to Cooper Crain (of Bitchin Bajas and Cave), who mixed it and sent it to the pair to sing over.

The songs were released weekly, from fall 2020 into spring of the next year. Now, they’ve been compiled onto the double album Blind Date Party. The selection of songs—from legends like Hank Williams Jr., pop stars like Billie Eilish, and outsiders like Johnny Frierson—are simultaneously fitting and surprising. The Dirty Three’s Mick Turner injects plaintive guitar into Robert Wyatt’s “Sea Song,” Bill MacKay weaves a subtle acoustics under Callahan’s wistful voice on Steely Dan’s “Deacon Blues,” and AZITA provides a hymnal backdrop for Cat Stevens’s “Blackness of the Night.” Some deviate wildly from the originals—like Crain’s reggae version of Iggy Pop’s “I Want to Go To The Beach,” or Dead Rider’s deconstruction of Callahan’s own song “Our Anniversary”—while others take a straighter path.

All together, the album is a testament to the familial nature of Drag City’s roster, a point movingly crystallized by a cover of Silver Jews’s “The Wild Kindness.” With the late David Berman’s widow Cassie singing along with Callahan, Oldham, and 18 other Drag City artists, it’s a cathartic, communal tribute to Berman’s legacy.

We talked with Callahan and Oldham about the making of Blind Date Party. Our conversation has been edited for length and clarity.

Merch for this release:
2 x Vinyl LP, Compact Disc (CD), Cassette

How did this project start?

Bill Callahan: With a phone call between Will and Dan [Koretzky]. After that, Dan immediately texted me with 12 exclamation points: ‘Will wants to do a duet record, are you in?’ Maybe they were question marks, not exclamation points.

Will Oldham: For Dan, that’s the same thing. 

Had you talked about collaborating before this?

Callahan: Not really. We had talked about touring with David Berman in a triple headline bill. When David died, that kind of transformed into this.

What were the challenges of adding vocals to finished music?

Callahan: When I make my own records, I tend to shape the music around my voice and guitar parts. So I had to learn how to do it backwards. It was like being in a room without a window or a door, and thinking, ‘How do I get out of here?’

Oldham: Most of [the music] was so shocking that I would try as soon as I could to figure out where my voice could go. So it was relatively live; none of the vocal takes were heavily worked over. It was an attempt to get it right in relation to the music, rather than any sort of objective success.

Callahan: When I make my own records, the first or second take is usually it. With this one, there wasn’t that whole momentum of the band, where everyone’s holding their instruments and looking at me, and the engineer is waiting and the clock is ticking. I still wanted to get it done quickly, but there was more labor in layering my voice and backing vocals, which I haven’t done since I used to record at home on cassette.

Oldham: For me, stepping up to the mic is not the time for a significant amount of deliberation and revision. All of that should have come before. Simone Biles doesn’t do her routine and then say, ‘No, no, let me redo that.’ Once I’m there, that’s when I show myself if I’m prepared or not.

Did your relationships with these artists influence the way you sang?

Callahan: Well, none of the tracks I got were phoning it in. So I thought, ‘Okay, now I’ve got to repay the kindness and do my best work.’

Oldham: There are a few people that I don’t know very well, like Matt Kinsey or Cory Hanson, so there was definitely an aspect of wanting them to understand how grateful we were or for the amazing work that they were putting in. And then there were people that I love as human beings, like AZITA, David Grubbs, Matt Sweeney, where there’s an elevated challenge. Bill and I had a couple of songs where we didn’t just take the music as is—we asked them to be revised. So [Leonard Cohen’s] “The Night of Santiago” from Grubbs was one that I challenged him on, and he challenged me back. It was kind of frightening and upsetting for a couple of days. I don’t want to challenge David Grubbs, because I’m in awe of him. He’s been one of the biggest musical influences of my life, and personally, I like him very much. So how do I go to him and say, ‘Would you revisit this, please?’ But I did. And then he told me, ‘Step down, son.’ [laughs]

Merch for this release:
2 x Vinyl LP, Compact Disc (CD), Cassette

The original version of “The Night of Santiago” is a Leonard Cohen spoken word piece that was put to music after he died. Did you have to find a singing part that wasn’t really there?

Oldham: Definitely. But for much of my life, I’ve listened to Leonard Cohen’s records, and I find him very difficult to cover in general—whether he’s singing or not. So whenever I hear a song of his and think, ‘Maybe I can add a dimension to this,’ I just jump on it. That song was one of the least interesting songs on that posthumous record, except for the fact that it seemed tackle-able.

A few of the songs deal with spirituality and religion, which has been a musical theme for both of you. But these songs are much more direct about it.

Callahan: I’ve realized recently that gospel music is way bigger in my musical development than I had even ever admitted to myself. I feel like I’m a gospel person who doesn’t believe in Jesus. Those songs are very powerful and uplifting, so they’re just fun to sing. It’s fun to sing about praising Jesus, you know?

Oldham: I’m so grateful that I’m not somebody who has been traumatized or scarred by organized religion. It’s not a problem to sing those songs for me. It’s kind of like singing in character, although that belittles the experience. It’s more like singing in translation. By listening to so much religious music and by going to church a lot, I learned how to translate many of the things that are said into something that I understand and share a belief in. So singing a song like [Dave Rich’s] “I Made Up My Mind” is a translation from one vernacular into another. I understand it emotionally, even though I also feel like I understand the mythological aspects of something like Christianity.

Were any of the choices songs that you thought more people should hear?

Callahan: “Deacon Blues.” [laughs] “I Love You,” the Jerry Jeff Walker song, is a dark horse of a song. A lot of people haven’t heard it. Getting my own personal version with Will singing it, I knew that was gonna be great. It’s the kind of song that disappears into a record in a nice way, like disappearing under a quilt. So I thought more people should know about that amazing song.

Oldham: It’s nice to have a shared experience when something is great and makes you feel good. And then there are the songs that are maybe mysteries to us, and we know that we get something out of the experience of spending time with them, and we want to dig deep and unpack the song for what it is, try to figure out. Potentially even with the idea of making ourselves better at making songs.

Merch for this release:
2 x Vinyl LP, Compact Disc (CD), Cassette

On the other hand, with “Deacon Blues” or Billie Eilish’s “Wish You Were Gay,” many people have heard the original. Did that influence your approach?

Oldham: Well, I’m gonna guess that maybe Bill, like me, kind of lives under things that look like rocks. Billie Eilish—I’d heard her on the Academy Awards sing the John Lennon song, but I had never had a conversation in which her name ever came up in my entire life, with anybody. So I have no idea what people think about Billie Eilish, or what their relationship to her music is. No fucking clue. I just knew it was popular, and I bought it at the record store down the street and listened to it and liked it.

As this project progressed, how did it change? Did you learn things that you used as it went along?

Callahan: Something I learned that I had forgotten about was the mystery of doubling something when you’re recording it. Meaning, recording it once and then doing it again—particularly vocals in this case. You do it once, maybe it sounds awful, but you do the same awful thing again and put them together, it sounds great. I think I used to know that 20 years ago, but I kind of forgot. Once I used it on one song for this, then I used it on a couple more songs.

Oldham: The experience of working on this got deeper and wilder. It grew. I read a lot of children’s books now to my child, and I think of Max in Where The Wild Things Are, the way his room grows. It became more of our reality as we went along. It’s something that I looked forward to each week when I was allowed to come in here to this recording space and work on the songs. We were deprived of so many things in the outside world that we were familiar with, so being able to turn to these songs was, to put it shallowly, psychedelic.

You both knew David Berman, as did many of the people who sing on “The Wild Kindness.” Was it hard to collect yourselves to sing that song?

Callahan: It took me a couple days, after trying to sit down and do it and feeling like I couldn’t get through it without choking up. There was the option of using those takes, but instead I waited until I could be a little calmer.

OIdham: It was the song that we needed to concern ourselves creatively with the least, because we were part of this massive semi-ensemble. I remember feeling okay about including a rawer delivery; that came with the security of knowing that it could potentially be hidden by other people [in the group vocal]. And a surprising amount of people agreed to sing on that song. Just about everybody who had participated in other songs, except for Cooper, and he had Haley Fohr [of Circuit Des Yeux] sing instead of him.

When you first heard everybody’s voices together, what was your reaction? 

Callahan: Extreme. Extremely moved.

Oldham: Yeah, extremely moved.

Merch for this release:
2 x Vinyl LP, Compact Disc (CD), Cassette

What do you think it is about Drag City that makes the roster like a family of sorts?

Callahan: I’ve been on Drag City a long time, and I think we’ve grown together, and are constantly checking each other, giving checks and balances anytime a new branch needs to grow. Drag City and I have done a lot of things for the first time together. And it seems to be a pretty democratic label that doesn’t just focus on their top three selling artists. All they seem to really care about is breaking even. Even now, if my record breaks even, they’re excited [laughs].

Oldham: It seems like they have a willingness, or actually an expectation, that the artist guides the way things are done, to lead the way and help define what Drag City is. They’re rarely like, ‘Well, that’s not how we do things.’ That is, unless you’re like, ‘Would you talk to my manager about that?’ then Dan would be like, ‘No, I won’t.’ I’ve talked to some artists over the years who’ve felt disgruntled at times, and I think it’s because they are expecting Drag City to take the lead on things. And I think Drag City expects us to take the lead on a lot of things. They’re like, ‘The reason that we asked if you would want to work with us is because we want to go where you want to take us. It’s not like we want you to be a part of us, It’s more like we want to be a part of you. We’re watching what you’re doing and we really would like to be a part of it.’ That’s great.

Merch for this release:
2 x Vinyl LP, Compact Disc (CD), Cassette

The things that were going on in the world—the pandemic, as well as social issues—was part of the reason that the record came about. How much do you think that influenced the actual music?

Callahan: I was definitely thinking about the audience in lockdown. A lot of times, you don’t know who your audience is, besides this little number of how many records you sold. This time, I felt more like I knew who my audience was, because I did find the pandemic to be a very equalizing thing. We’re all humans, and we can all get viruses and die or get sick. The same thing happened when I had my first kid—when I saw other parents, all of a sudden I had something in common with strangers. I’ve never spoken with you or met you, but I know a little bit about what your life is like. And I had the same kind of feeling with the audience for this record: I maybe know a little bit about why you’re listening to this record, for once.

Oldham: I often thought, ‘Is there any way, without weakening it or potentially even destroying it, to somehow incorporate some of the other things that everyone was going through?’ Specifically the sociopolitical upheaval—being here in Louisville, this was an epicenter of some of that, because Breonna Taylor was such a significant figure in people’s minds.

But we had a lot on our hands just with all this music. It had such immediacy. One of the reasons that I think that we tend to like live recordings, or first or second takes, is because we are responding to something real that’s happening in the recording environment. And here we are responding to something real that’s happening on a much larger scale, and we can share that fairly quickly with the audience. So in terms of having an active communication with the audience, we’re making something that applies, ideally. That was pretty much unparalleled.

I like thinking about the stories of the old Chess Records office, when they would cut a song and then play it on the loudspeaker to the sidewalk. If people danced as they were walking by, they’d say, ‘Let’s press this many copies of that one, because it’s going to be a hit.’ I’m often frustrated when I hear that the streaming services and journalists need this much lead time. I think, ‘Well, okay, so I’ve already made a museum piece.’ I was trying to make some music that was related to what people are experiencing and listening to and living through right now. With this, we actually could do that. And as Bill said, we had more of a common predicament than we ever have before in our life—and hopefully ever will again.

Does putting this album out represent the end of the project, or could you see it continuing?

Callahan: I think neither of us wanted it to end. So we added to it—we did a Jerry Jeff Walker song and a Scout Niblett song that aren’t included on the album. But now that the album is all done, as things do when they are done, it seems done.

Oldham: I have found my mind drifting towards [a question]: ‘Is it possible that one day that we could get as many of the participants together as we can manage, and play this series of songs from beginning to end? Not as much about a performance on stage as about hanging out with each other? That seems like it’s happened enough in my mind now that it probably doesn’t have to happen for real. But at least I can imagine it would be a wonderful time with each other.

Callahan: Do you remember your idea about the pickup truck, Will?

Oldham: What was that?

Callahan: Where we would be in the back of a pickup truck in lounge chairs, just playing the backing tracks and singing along. And would drive away if not enough people were dancing.

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