Okkervil River was part of a class of Austin indie rock band that broke through in the early ’00s—along with …And You Will Know Us By the Trail of Dead, Explosions in the Sky, Spoon, and others. Twenty-one years since the band’s founding, they’re still active, too, despite countless lineup changes and frontman Will Sheff’s tendency to de-camp from Austin to New York to Los Angeles. But the music business is changing, and the ways that artists made money when Okkervil River debuted is very different from how they make money now—and how much money is available to musicians now has changed, as well. With more than two decades of good will built up among his band’s most ardent fans, though, Sheff launched A Dream in the Dark: Two Decades of Okkervil River Live, a subscription service offering a twelve-album cycle of live recordings, released exclusively as digital downloads (one a month for a year when you sign up), documenting the band’s history in exacting detail. The two tiers of subscription levels—$75 and $125— include extras, like pre-sale tickets to summer shows. (Each album in the series is also available on an a la carte basis from the band’s website.) Texas Monthly caught up with the loquacious frontman to discuss the artistic process of archiving your entire life, the reality of being a musician in 2019, and how tech companies are changing our lives for us—without thinking through the implications.

Texas Monthly: The music industry is tough, and this seems like a clever way to create something that your fans want. Where did the idea for this come from?

Will Sheff: Forever and ever, I’ve always had an archive. I’ve saved everything related to the band and every recording we’ve been given of ourselves, and whenever I’ve had a chance, I’ve spent money—sometimes a lot of money—to record us as often as I can. I tend to archive my entire life. It’s just something I’ve always done. But more recently, we hit the twenty year mark, which is a crazy thing to think about. I had lived in Austin for about ten years, and then I lived in New York City for ten years, and then I wasn’t sure where I was going, when I found my way to Los Angeles when my partner got a job. And I found myself in this retrospective mode, where I was looking back on twenty years of my life, trying to see what it has meant and understand what it was I created, and reflect on the times that I had and the people that I had them with. Part of the reason for that was that I felt a sense of accomplishment, but also I was trying to look forward, and so I was looking back to put a cap on things and file it away. I approach this almost as a giant alternative version of my career, because I’ve put out nine albums, and now I’m about to put out twelve live albums, and often I’ve thought back about how I wish I could re-record something, You write a song, and then you make a record. You release that recording, and then you go out and play those songs a million times on tour, and by the time you get to the end, you think, ‘I wish I could re-record that album right now, I’m so much better at playing these songs now.’ You start to live with a song, you start to hear different ways of playing it, of interpreting it, of hearing it. So this is kind of a chance for me to re-present the songs I wrote in an alternate way that’s more nomadic and off-the-cuff and in-the-moment and collaborative than the original, manicured studio creation. So I’ve been trying to approach this as a big, large art project that can present what I’ve done for twenty years to people in a new way, and to maybe move onto something else somehow.

From a music business standpoint, it’s no secret that musicians are doing poorly. I do think, though, that a lot of people who don’t work in music—who don’t actually count on music to put rent in their landlord’s bank account—don’t actually understand how hard it is. Everyone I know is so freaked out. They’re all groveling before Spotify and a lot of them are hanging it up. There’s a sense that you work so long and so hard, and some of the sacrifices you have to make to try to make music for a living are pretty tremendous, and there’s a sense that I hear from people who are very emotionally worked up when they talk about it, is ‘What do I get for all that work?’ In a normal job, you’d assume you’d build up some kind of equity for your work. But that’s completely disintegrated, and for an arbitrary reason—the tech companies just kind of create something, and then it just disrupts and destroys. There’s a lack of compassion that we have toward musicians. A lot of people don’t believe that musicians are actually doing real work. So it’s a deeply, deeply insecure time, and everybody is trying to stay afloat, and that includes me. So to some degree, this was born out of a desire to have an artistic product that I could fully control, and be able to make some money off of something that I’ve had for a while. You try to come up with all different kinds of ways to make ends meet, to make yourself whole, to keep doing it. And it does to some extent come out of that—but it also comes out of the retrospective and curatorial urge. I really love a challenge, and I really love to do something ambitious, so the concept of doing twelve live albums for 21 years seems like a really big challenge.

TM: This project is obviously very curated and done with care. In an era where music is so commodified, we’ve seen artists sometimes tax their fanbase to pay their bills with lazy merchandise and products.

WS: I don’t want to break my unwritten contract with the audience, which indicates that I’m going to put my heart and soul into something. I’m not necessarily going to be a crowd-pleaser every time, but if you purchase something that I’ve made, you know that I’ve loved it and cared about it and paid attention to every detail. I don’t take for granted the fact that I’ve gotten to do this. I don’t believe I inherently deserve anything. I think I worked my butt off to get here, but I’ve gotten to do this for 21 years, and I respect that deeply, and I’m thankful for the people who let that happen, and I have a contract with them. Every single artwork should be  held to that—you’re only on this earth for so long, if you’re going to take 12 hours from your life to listen to my records, I want to make it worth your while. If you’re going to take two hours to watch a movie, that’s something to take very seriously. People can be mercenary about it, or phone it in, but for me, I think that being an artist is just as serious a profession as being a doctor or a priest.

TM: Does the 21-year history you have with your audience that says that you take it seriously help you, in terms of marketing a project like this? If your band is launching a subscription box, do you think people assume that means it’s going to be a good one?

WS: I think that fans of my band know that I care. I hear that from them a lot. I know enough about how I’m perceived and I have enough faith in how this works to know that people who follow the band know that I don’t phone things in. Then there’s the whole sea of people who may or may not pop their heads in, and they come and go and ebb and flow and they can turn into hardcore fans, or they can pop in and then take off—and there’s nothing wrong with that, that’s why we did an a la carte option for all of these, so if you were really into the band in 2012, or 2003, or whenever, you can just check out that one show. That’s fine, too.

Around the time I was in my late 30’s, I went through a period where I wasn’t connecting with myself the way that I wanted to, before I made Away. I felt like a sense that I needed to reinvigorate things and start it fresh. One of the things I started to interrogate about myself is why I do this, and why I keep going, because it isn’t about money, certainly. I don’t think it’s really about ego gratification, although that’s part of why it started out, and maybe some score-settling, too. But that stuff doesn’t really make you very happy. But deep inside, it’s about wanting to manifest something beautiful into the world that might bring pleasure or joy or healing or fun for people. I’ve been lucky enough to hear from fans about really crazy things in their lives where the music was one of the helpful things for them. Hearing those things right around the time I was questioning my role in art really helped put me back on track around 2013 to 2016. So I think there’s a real closeness with the fans and me, and I think they understand that when I do something, I’m going to do it with my whole heart. Even if it’s a business thing, too. I don’t necessarily think that business and art have to be separate from each other. Maybe I should be ashamed to be a capitalist in that way. But there is a part of me that likes the good, old-fashioned idea that’s like, ‘I have a thing you’re going to like, will you give me a fair price for it?’ And I think I hold up my end of the bargain.

TM: This seems like a creative way to sell things to an audience that wants them, and it comes from a pure place.

WS: Oh, certainly. I just love delighting people. Which isn’t to say that my work is going to delight everybody—certainly far from it—but you know that feeling, like when you go to a movie you know you’re going to like, and the lights go down and the titles come up, and you feel a little thrill run through you? That feeling is one of my favorite things to kindle. I’m just so pleased that there are people who find what I do entertaining, and I saw this as an opportunity to super-serve those people.

TM: You have nine albums, but twelve albums in the set. Where’s the overlap between different eras of the band that isn’t reflected in those nine albums?

WS: Music is a really funny thing. If you ever sort of sit and think about ‘What is music?’, people are twanging on strings and they’re vibrating and they make a sound, and other people really like to hear that sound, for some reason that I don’t think we can fully explain scientifically? And then you think about the bigger thing around that, how music was practiced in the 20th century and how it’s fragmenting in the 21st, it’s such a strange thing to think of, tracing it back to something as simple as just slapping on a drum and singing to your friends. It’s funny that a song becomes only one thing. We think of “My Girl,” and we think of the recording of “My Girl.” But I like the idea that a song has a soul beyond its recording. There are songs of mine where I think, “I love this song, but the recording didn’t quite get the fullness of what was good about it.” I think that’s true for even great recordings—there can just be a beauty and a richness and a depth to certain songs, so I’ve always liked the idea of being able to re-present the songs. Fans of the band will know that I’ve gone through and completely re-organized and rearranged songs many times throughout the history of the band. So if you subscribe to this whole series, you might hear four versions of the same song, and one could be a 6/8 waltz time ballad, and one might be an uptempo disco number. They could be completely different. I’m trying to think about the exact overlap, but the way that touring and album cycles work isn’t exactly one-for-one from album to album. You sort of get lulled into thinking that’s true, but it’s only a frozen moment in a band’s development. So some of those extra records will show some amount of development of a band between two records. So maybe I would put out two releases, because we started a tour and I would put out one thing, and then two and a half years later, before we start to record the new album, we’d be a completely different beast. So I wanted to be able to present the range of that.

TM: These aren’t being released chronologically. Is the order you’re releasing these in a preferred listening order, or is it more random than that?

Will Sheff: It’s not random! I’m still figuring it out. It’s not chronological. People can listen to them chronologically, and that would be a fun way to listen to them, but it’s more prismatic than that, jumping back and forward in time to show us in different moments. Some will speak to the ones that came before, on some level, and some will be complete departures. It’s kind of a portrait of this band. We’ve had so many different members over time. I started this with two of my high school friends back in 1998, and over the years—partly because of the financial insecurity we talked about—people come and people go. They decide to have families or whatever and they filter out, and some of them might filter back, too. I’ve been so lucky that as I’ve grown and changed, I’ve had new people coming in and accompanying me along the way. But only I remember all of them. Sometimes I sit in the van with the current lineup and I think, ‘I’m the only person who remembers every single one of the people who’s been in this band!’ Fans might think they have a favorite era, and band members remember their era, and different members who came in and out, but I’m the only person who remembers the whole thing. So this is my chance to tell, to the hardest-core fans or maybe just to myself, that story of every last person who came in and out of this band. So I’m trying to show the kaleidoscopic bigness of that. It’s my entire adult life.

TM: These aren’t going on Spotify or other streaming services, which makes sense when you’re selling digital downloads. But this is also obviously a very personal project. Do you find that those services turn the art into more of a commodity?

WS: Well, yeah. This is a difficult thing to exactly explain, but it does seem like life becomes more and more trivial as we go on. The ways that we used to relate to our friends, or listen to music or read a book or send a letter or watch a movie—they’re all changing. And they’re not changing fueled by our own organic behavior. They’re changing because companies in Silicon Valley, in association with giant corporations, have decided they want to change them. And we just kind of go along. We had records and cassettes and CDs, and then that got completely undermined, and we had iTunes and all of that. I thought that was still an all right system.You had some amount of power, and some amount of ownership. Now, everything is streaming, and everything has the illusion of being free, so it’s so much harder to feel it, and deep dive into it. I’m not saying that you can’t—I use streaming services, and I like them, but I use them in conjunction with other things, too. I still do listen to digital files on iTunes all the time. I’m living in fear of iTunes being destroyed by Apple, because I’ve spent 20 minutes a day for the last fifteen years of my life organizing my iTunes, and that’s all going to get destroyed by them, because they’re going to decide that they can make more money some other way. But I think that the norms and traditions of our society are getting eaten away at—not just in terms of how we listen to music, but how we relate to each other. You picture, instead of community and a neighborhood where people know each other, a whole bunch of angry fucking people on Facebook. I think we’ve been sold down the river by these tech robber barrons, and they’re destroying the fabric of our culture, and music is just a small part of that. A lot of these people don’t think they’re doing bad things, but they haven’t thought it through very much—or maybe they have a nagging voice in the back of their heads that tells them they’re doing something bad, but then they have a much more nagging voice that tells them that they’re providing for their families. I’m not a purist or a luddite living in isolation—I use this stuff—but think about the power of music. When something really awful happens in your life, and the first song that made you feel better after that, and how much gratitude you might have felt? You can feel the power of music. When you think about songs from your childhood that help you remember people who have gone away? You really understand and can feel the power of music. When you go out to see a show and you’re completely transported and forget your troubles, that’s when you can feel the power of it. Music has been used in religious services by every single culture across human history, basically. It is a powerful thing that we have, and it is being treated as just content for the content mill. And that makes me sad. It truly does.