Will Oldham on Death, Wonder Showzen, and Returning to Louisville

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Today's installment: Will Oldham is an absolute legend, I've followed his career and loved his music in its various forms basically since I was able to seek out music on my own. After a long hiatus from releasing non-covers records, Will fired up the Bonnie "Prince" Billy generator back in 2019 with I Made a Place and has been on quite the run ever since, with the imminent We Are Together Again (out this Friday) standing tall as one of his best in a minute. I was truly honored to have such a distinctive figure in American music hop on a call for this newsletter a few weeks ago, and I was also taken aback by Will's candor and willingness to dig deep into his past and present. This is one of my favorite interviews I've ran in a minute, so soak it in and check it out:

This record continues your streak of what you've referred to as "Louisville records." Unpack what that means to you.
It was a slow realization. Of course, I come from here, and I had a pretty awesome adolescence and a lot of creative engagement with pretty spectacular individuals and organizations—a lot of foundational musical experiences that, I won't say I took them for granted, but I was new to Earth, new to existence, so it was something I participated in fully, but I didn't know any alternative. It didn't feel like there were a lot of choices, because all the options that I had were great ones, especially musically. There was also a fair amount of Louisville scene pride. So when I knew I was leaving home at the end of my teens to attempt a higher education experience and, when that failed, to explore potentially working as an actor, I got a tattoo of the symbol of Louisville on my left wrist, thinking that wherever I went in the world, I could always look down and remember that I have a community to go home to that helped build me.

I was making music, living different places, having different experiences, and then I had to come back here in the early 2000s because my dad died unexpectedly, just as my mother began to exhibit symptoms of early onset dementia. I somewhat reluctantly realized that I was going to potentially be here for a little while. Since 2006, there's been a lot of challenges, but in order to survive, I needed to figure out how absolutely great I could make living in Louisville be. It was a continuous exploration that, ultimately, was extremely rewarding. It was by necessity that I did this, but at the same time, the resources were here. I didn't really have to create anything. I could just explore what is here.

Through that, I also began to understand that—I've never read Proust's Remembrance of Things Past, that's the big one, right? Where he's in bed and he writes 700 pages from one spot? Is that correct?

I don't know, but it could be right.
So I was essentially realizing that I could probably make music that was more interesting to me—and more interesting—to audiences by continuing to go deeper into what staying in one place offered. And this is a place that I had wonderful experiences in, wonderful access. It has a really rich, complex cultural identity and history. Then I started to think, "Well, if I really dig into this, it's going to be something that other people aren't able to make." It's going to potentially fill a void of exploration—of place and personal experience—that perhaps listeners also are missing.

Oftentimes, even some of the best musicians ultimately leave themselves behind, and they're accessing a fairly shallow resource when it comes to how they build their music—especially when musicians have long-term success. They start to be self-referential, and their self is increasingly less interesting because they aren't connected to any sort of history, community, and culture. Their world becomes everything, and I don't find that very interesting at all. I'm trying to not ignore my privilege and responsibility as a decision-making human being on this Earth—especially when the ground was pulled out from under some of us, with the onslaught of everyone abandoning previous listening practices for streaming music, and realizing how much that changed and devalued so much of what I held dear in listening to and making music.

There was almost a decade where I just thought, "What the fuck? Why am I doing this? What is this all about?" If streaming music were a thing when I was younger, I would not be making music right now. It's disgusting. I would do something else. But this is my life, so what am I going to do? I'm going to continue to try to make records.

So I made this Everly Brothers thing, this Merle Haggard thing, this Susanna Wallumrød thing, and this Mekons thing, which was great. I learned so much, and we had a ball with all of these things. They were hard and challenging, and then when I thought, "What should I be doing?" a friend was like, "Here's this artist residency that I thought would appeal to you." It was in parallel with the National Parks—an organization that arranges for artist residencies in U.S. national parks— and one of them was at the Hawaii volcanoes. My wife and I joint-applied and got accepted, and they just gave us a government-issue, rudimentary cottage on top of this active volcano in January 2018. All of a sudden, I was faced with an extended period of time with no internet connection, in the middle of this amazing space. I thought, "What am I supposed to do?" Then I thought, "Well, I guess I should write songs."

When we finally came home, I had these songs, and I was like, "I guess I'll just edit, rewrite, and practice the songs." After six months or so, I thought, "I guess I should record them." I was in Louisville, newly married, and records don't mean anything to anybody anymore. They used to be financially sustaining for me, and they're not anymore because of streaming—so why make it? And I thought, "Well, because that's what I do, and this is a great place to do it." I looked around and thought, "Why not make its value be about life and community here?" If it has no other value to anybody else, it has that value to me, my colleagues, and my friends in my community—and it felt good when we did it.

I Made a Place came out, and it seemed like, "Okay, yeah, this is what I do. All the forces have combined to make this—something that I can do that someone else can't. There's a weird, unique combination of circumstances and forces where you can make these records here with these people, and it can be potentially a good thing." Then, [Matt] Sweeney reached out and was like, "Let's make a Superwolf record." Then I made Keeping Secrets Will Destroy You, which was this deep exploration of these incredible people who are involved in music in Louisville. I made The Purple Bird in Nashville, and then I was right back into the Louisville program with this new one. We're together again.

You mentioned earlier how, after moving back to Louisville in the 2000s, you experienced some challenges over the years. What were some of those specific challenges that you experienced?
How do you mean?

Well, coming back home, there's always ups and downs in terms of how life plays itself out, so to speak.
Really specifically, it was just crazy. I'll oversimplify it and call it the one-two punch of my father's very surprising death...I'd stopped here for a little bit to make Master and Everyone with my brother Paul, and it didn't work out. But at the same time, I thought, "Well, maybe I'll spend time in Louisville for a while," because I ended up making that record in Nashville with Mark Nevers with Paul playing on it. Then I thought, "Maybe I'll live in Louisville for a little bit." I tried it for a couple of years and thought, "Nah, I'm going to go to California." We just made The Letting Go in Iceland, and I packed my car full of stuff and drove out to California.

I had an appointment in Santa Cruz with a landlord to rent a little tiny cabin in the woods there, which I was very much looking forward to. I was shooting a video for "Cursed Sleep" at this falconer's house in Atascadero, early on a Sunday morning,m dressed head to toe as a bird, and I get a call from my mom saying, "Something terrible has happened. Your father has died." The earliest flight I could get was late that night, so we finished shooting the video that day—which is crazy to watch, because I'm sitting there in a daze wearing a bird costume—and I fly home.

I'd talked to my dad about my mom's mental state, so I was thinking I'd probably stick around and see how that plays out. It turns out that it was the beginning of full-blown Alzheimer's, which is a challenge. She was in her early 60s, and I didn't have any peers who had experienced that. I had a support system of friends and loved ones, but nobody with experience. It was just a constant, daily exploration of how to cope while trying to maintain some sense of selfhood. I was creating music both because I relied on it as my living, but also because it's who I am—while grieving the loss of my dad and the ultimately far more difficult grief of witnessing the active loss of the other parent.

My mother became an aggressive person for a number of years. Nobody wanted to be around her, because she was mean. She was never mean prior to that point, but she had endured, I guess, a lot, and was trying to deal with that. So here I am in Louisville, with streaming music taking over, dealing with all this stuff. Ultimately, her care required so much attention that touring was a big challenge, because if I went away for more than a week, whatever support system I had with like caregivers had the potential to crumble because my mom was such a bitch at that time, just because of her disease.

In addition to the challenges of the disease itself physically, eventually she just became nonverbal and non-mobile. She knew she didn't want to leave her house and go into a nursing home, which is what a lot of people do. At the same time, my dad had saved up money for their retirement, and financially she could stay at home. What do I do? Put her in one of these insane, inhumane prisons that for some reason Americans think are okay? My whole life, I've always thought, if we can't value our elders, what are we alive for? I was thinking, "My mom's got to be at home if we can afford it financially"—but it took so much work.

I was also facing the disconnection of trying to have a life in music in a place that has an incredible music community, but not one that's involved with the world outside of Louisville—and my world had expanded to include communities all over the world. I toured different places, and there were audiences there that sustained me creatively, financially, and socially—and I didn't have as regular access to those during that time. Fortunately, I ran into an old friend from high school who worked for the public library system here as the immigrant and refugee outreach librarian. She took her job very seriously. She was like, "Why don't you come to one of these sessions where people volunteer to tutor English to new Louisville people?" We have these great refugee resources here in Louisville—which are challenged by the current administration—because we have significant international populations, many of whom are refugees.

So I started to go to the library once a week, and essentially I became her assistant doing outreach—going to various libraries and community centers where the international population congregated by desire and necessity. I started to learn about the Cuban Louisville and the Somali Louisville, and it was completely amazing. I was still working on music and had a brilliant, amazing, solid, beautiful ensemble for a while. It was the three of us from Louisville and three out of Chicago, which was Emmett Kelly, Ben Boye, and Angel Olsen. It was relatively easy to get to Chicago and for them to get to Louisville, so a lot of groovy music things happened.

But between trying desperately to keep my music going while dealing with the family stuff, I didn't have anything resembling a social life for six or seven years. I sort of missed my mid-30s into my early-40s. I didn't experience that decade of life. At the tail end of my mother's life, the fates were very kind on some level, because she died in January of 2020—which, if she had lived two more months, or longer, I think it would've killed me. I literally think it would've killed me to deal with what she required for her care and the pandemic at the same time. I don't think I'd be alive today—because, at that point, my health was failing. It was just so stressful, an absolute nightmare.

But I did have some strong projects and creative connections, and I ended up meeting Olivia Wyatt, because we acted in a film together that never came out in which we played husband and wife. At one point, she came to Louisville with her boyfriend, who's from Louisville, and she was like, "You want to come over to my boyfriend's family's house for New Year's dinner?" I went and ended up meeting another Louisville-ian who I'd never met before, falling in love with her, and marrying her. We have a kid, and lots of great things happened. But I've really been forced to face certain things about my existence that do make the music more valuable to me—but I think it is to other people, too, because of the things that I've been forced to put into it.

What was the pandemic like for you?
Heaven. It was so great, partly because—honestly—my mother had died in January. I'm not sure she'd spoken a word in three or four years by that point, and she was totally non-ambulatory. She lived longer than she was expected to live, because I took such good care of her, because I didn't know what else the the fuck to do with my life. But it was such a weight off when she finally passed.

We'd had a child in November of 2018, so in March of 2020 she was a year and a half. She didn't have social awareness, and the most important people in her life were her parents. All of a sudden, she's given the greatest gift a child could receive, which is the absolute almost 24/7 attention of both parents for this part of her life. We got to be with her all the time—and because she slept a lot, my wife and I also time to work. In talking one day to [Drag City co-founder] Dan Koretzky, I had this idea of working with Bill Callahan on Blind Date Party, and that was one of the greatest creative projects I've been involved with in my life—an uplifting, thrilling thing to be involved on a daily basis for nine months. I was able to channel a lot of the confusion, pain, anger, and loneliness into something that was collaborative, communicative, joyful, new, satisfying. I got to work with people that I probably never would've been able to work with—who I admired—learn new things about singing and work. I could just work on music for all day, every day, except for family stuff. There was so much bullshit that we didn't have to deal with—and the bullshit that we did have to deal with, Blind Date Party and having a one-and-a-half year-old made it heaven.

But I'm not oblivious to how much suffering other people endured—the tolls that the pandemic took on people, the lives. Of course, the pandemic, if it wasn't intentional—I'm not going to be conspiracist and say that it was—but it was an opportunity for forces in power to consolidate power in really dark, apocalyptic ways in the same way that we experienced post-9/11. It was an opportunity for people to take advantage of power for decades to come, if not for the rest of our our existence, and that's absolutely horrific—but we had a ball at the same time.

Given that we're talking a lot about the last 20 years for you, I'm curious to hear what your relationship is with memory in general.
I think I have a decent memory. On a really brass-tacks practical level, one highlight of the past 20 years was when—first of all, I'm not necessarily the biggest overall fan of the artist-slash-entrepreneur known as Bob Dylan. However, there's a mid-period—which I would call effectively a late-period, in terms of his actual creative output—song that's co-credited to him and Sam Shepherd called "Brownsville Girl" from Knocked Out Loaded. It's one of my favorite songs of all time, and around 2000 I tried to perform it live but it was just too long. Then, at some point around 2012, a friend of mine in town who puts together weird amazing collaborative benefit shows said, "I think you like this song. How about if I put together a 15-piece band and we'll do it?" I was like, "Okay," and then I thought, "Well, I guess I should memorize it"—and I memorized it. What was the problem? I don't know why I couldn't memorize it before.

Then David Lowery came and said, "I want to make a short film called Pioneer. Would you want to do it?" I said yes, and the script was essentially a 16-page monologue. I thought, "Well, what do I do with this?" I'd acted all my life and always had problems with memorizing lines. But I memorized it, and we filmed it in these 30-minute continuous takes. From then on, memorization has not been a problem. It's this wonderful thing, realizing that your memory—your brain, and the way that it works—is not necessarily set in stone. You have access to modifying how your brain can function. Even if you think, "I could never do that—my brain doesn't work that way," it's not necessarily true, and that's exciting and thrilling, to face the rest of one's life thinking, "My brain can become something new for me."

As for memories—I mean, I'm not a nostalgic person, really. I find that I think about the past more with a child, because I feel like it's good for her if I say dumb things like, "You know, we used to have phones that were attached to the wall." It's important for her to know that the past is part of our present, and that's a part of the future. I'll constantly bring up things from my past that are cultural observations or facts. Otherwise, I don't feel like my memory is pretty good, for the most part. For some reason, circumstantially, I switched schools a bunch between nursery school and sixth grade, and then I stayed there.

Essentially, that broke my brain in some ways where it doesn't work like other people's, because other people could rely on collective memory in a way that I couldn't. They just knew we did this thing together, and they don't have to talk about it—and I didn't have anybody to talk about collective memory with. As a touring musician and an introverted artist, I have a lot of experiences and perspectives that are, for better or worse, unique to me. That means I don't have a lot of the collective memory experience that many of the people that I associate with have, so the way my memory works is kind of different.

Ultimately, one of the cool things about living where I grew up is that, for the most part, every square foot that I traverse on any given day is full of layers of memory and experience—everything I do, everybody I interact with, every store I go into, every street I drive down. It's very complicated, but it's a resource, and I've learned to think of it as an advantage that I have in my life—the first place I had sex, going to visit my dad at work downtown, eating a hamburger, seeing music in lots of places. It's available to me in surprising ways every day which I take to be a wonderful phenomenon.

Tell me what you've learned about the world and yourself from being a father. What has that experience been like for you thus far?
It's ever-changing and ongoing. She's in rapid development, and she's seven, which people have told me a couple times is the age of reason—and it's very true. She is able to compute and analyze in wonderfully independent and radical ways, which is really thrilling. We're adding a bathroom for her in the house and there's other renovations that are involved with that—because you can't just do one thing—and my wife and I were arguing about it weeks ago. After the argument, I said to our daughter, "I'm really sorry you had to witness that argument. That was really rough." And she was like, "It's just a house." And I was like, "I know, and sometimes your mom"—and she was like, "No, I'm talking to you too, Dad. It's just a house." I was like, "Thank you. You just saying that is, in so many ways, one of the greatest gifts anybody's ever given me."

I've always loved kids, and I have a slew of godchildren. Thinking about things through kids' eyes is just something that's been a part of my the way I see things, to some extent. Before we were married, we had a brief discussion about, "Do you want kids? Why would you have a kid in this day and age?" I said, "To raise a post-apocalyptic warrior," and my wife said, "Okay sounds good to me." If you look at the news, you have no reason to think that you should be doing anything else with your kid than gradually and gently guiding them into the role of Furiosa. I'm not going to take her to a survivalist camp or anything like that—not in the next year or two. Maybe someday.

But that mindset is just trying to arm her with critical skills and an awareness that nothing is to be taken advantage of—and the reason we're here on Earth is to love and be loved, and to help other people that are completely fucked, because this world is not going in a direction that's going to be easy on any member of the population.

As far as being a public face and figure is concerned, I'm really curious to hear you talk about how you navigate how much you give of yourself. From our conversation, it sounds like you've done done well enough to avoid being online, for the most part. But from when you started making music and through becoming—let's say, a known entity in American music—a lot has changed in terms of how one deals with the public, and being in public.
It's a pretty huge question. I'm glad that I get to continue to do this work. Another great thing about deciding on a methodology six years ago is that the songs themselves benefit from it, because so much of the past 35 years of making music —the decisions about how to make music are, in some ways, the medium that I work in, as much or more than the music is itself. Every decision is a part of the creative process. I've always eschewed aligning myself with a controlling record label or management because that takes away half of the fun. Why would you want to give up all these decisions that will ultimately affect how good your life and work is? I don't understand it.

I've said this for years, but a fantasy of mine is that one day I will come up with and copyright a song somebody else will cover, and I'll get mailbox money for the rest of my life—because I'm not interested in, or comfortable with, being well-known. Of course, it's an asset. If you're trying to make a living making music, you have some sort of notoriety. But beyond that, there's nothing about it that I want in our lives. So I try to work as hard as I can with the understanding that having some public awareness is crucial to being able to do the work in the first place, until I get that mailbox money. There can be good things about being well-known, but it's about being super careful about it and trying to not make decisions that I would regret.

Sometimes, I feel very alone in looking at people's willingness to not be considerate about decisions that they're making—or not making—when it comes to their engagement with online activity, and giving over things to entities that we know are ill-intended sure. Instagram is awful, and everybody knows it's awful. They're even making it illegal in certain countries because it's awful—and, yet, people don't question it. They don't look for alternatives, and they fully engage with it in ways that I find alarming, disarming, disturbing, and upsetting.

I do take heart in the fact that it seems to be falling over itself, and shooting itself in the foot. I have no problem not spending time on Instagram, because it's uninteresting. In the past, when it was more streamlined and straightforward, it was just, "Here's a bunch of pictures—that's it." Now it's like, "What is this bullshit? Turn it off! It's awful." I also know the kids are smart, and teenagers will say, "Why do you do this stupid thing? It's so stupid, and you look like an idiot when you do it." I don't know what will replace it, but unfortunately it's a tool for our profession that is, at this moment, unmatched in its utility—which is an everyday challenge.

It's funny that you're talking about Instagram specifically here. At some point in the mid-2010s, Robin Pecknold of Fleet Foxes told me it was the only platform he liked, because it was just pictures. 10 years later, it's very much not that anymore.
Yeah, I remember I was on a tour with Bitchin Bajas before we made our record together, and my friend Oscar, who sells my merch, was like, "You should get on it." Every time wed pull up to a toll booth or check into a motel, I'd ask the clerk or the toll collector, "Are you on Instagram?" Invariably, they'd say "No." So I was like, "Okay Oscar, I don't know why I'd get on it." Ultimately, I got on it anonymously, because there were neat things that I could look at anonymously—people who I'll never meet in my life, who I became kind of connected to. It was neat. Then, it got uglier and uglier. As a utility, unfortunately, it's ultimately counterproductive. There's no utility for a lot of normal people at this point.

I'm doing press for this new record right now—a lot of overseas press, mostly Europe—and there's a far more active music criticism scene still happening over there. Here, it's gone. It's insane. Our press is gone. We're not Palestine under siege, where they're just murdering all the journalists. They're just silencing all the journalists here, and people are going along with it. There's no having compelling and productive conversations about how, when, where, and why we do music. It's unavailable to us, except in your own living room or whatever.

I mean, that's why I run my own publication at this point.
Well, I appreciate you.

You've obviously done a lot of acting over the years. One thing that you've done that's always stood out to me was the Wonder Showzen episode "Horse Apples." Talk to me about playing to the comedic end of things for you.
I was such a big admirer of those guys and their work. That show specifically. but also other things they've done, like Doggy Fizzle Televizzle, The Heart, She Holler, and Xavier: Renegade Angel, which i also did a voice for.

Johnny Cash recorded one of my songs, and I got to be in the room with him, sing with him, and talk to him about the song—and I got to be on Wonder Showzen. Those are parallel experiences, because these are people who whose work blows my mind, who I spent a lot of time having a visceral reaction to their work and feeling very powerfully inspired. Then you're thinking about it like, "Whoa, now that I've listened to the song a hundred times or watched the show so many times, how and why does it exist?"

My thoughts about my work on Wonder Showzen are mixed. One reason I didn't feel it was realistic to be an actor is because I thought I wasn't enough of a person to be a good actor when I was 18 or 19—and I still feel that even now. In the past five or six years since having a child, I've felt like I'm enough of a person to make music in a way that I want to make it. So I'm glad I got to do Wonder Showzen, but it was an overwhelming experience, and I wish I could've done it better. It was just a privilege to be there, and it was a great episode of a remarkable piece of modern culture. But I don't necessarily think I lived up to the task.

I mean, it was really funny.
Probably funny, but that was all them. I wish I could say that I helped make it funny. I was in Jackass 3D, and I think I did a good job in that. I brought my A-game as a present, improvisatory, down-for-anything artist, and maybe somebody else who wasn't a regular Jackass crew member could've done as well as I did. But I think there are many people who could've done my Wonder Showzen appearance much better than I did. But it doesn't matter. That's not what it was about, and they were happy with it.