Gotta Start Somewhere Okkervil River’s Will Sheff

John Vanderslice

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No matter how successful entertainers become, they’ll inevitably always remember the first gig—whether it was disastrous, wonderful, or absurdly strange. Gotta Start Somewhere embraces these nostalgic moments by asking established entertainers to retell the story of the first time they ever graced a stage. In this edition, The A.V. Club caught up with singer-songwriter Will Sheff of bombastic indie-rock outfit Okkervil River. On the heels of Okkervil’s recent album I Am Very Far, the group will play the Pabst Theater Wednesday, Sept. 21.

Will Sheff: The first time I ever appeared onstage—I may be wrong—was in a Christmas pageant that my whole town put on. I come from a really, really small town—a 500-person population town—and every year the townspeople would put on a Christmas pageant. I believe I was baby Jesus in the pageant. But as time went on, the people in my town got sick of the same Christmas pageant over and over again, so they got ambitious and decided to start doing musicals. There would be these community theater productions of The Sound Of Music, Oliver!, and stuff like that. When I was in maybe fourth or fifth grade, I went in and did an audition, and I was really nervous about it. I don’t remember what song I sang for my audition, but I clearly remember that I wanted to sing “The Long And Winding Road” by The Beatles.

The A.V. Club: When you weren’t auditioning for musicals, did you have any early bands?

WS: I did. Like I said, my town was small and there wasn’t much to do. We didn’t really have cable TV, and this was, of course, in the days before the Internet, or at least before I was aware of anything like the Internet. You really had to make your own fun. I remember that I used to have bands with my brother. They were all pretty much theoretical bands. I wrote songs in my mind, and they didn’t have any musical accompaniment because I didn’t know how to play anything. I would just write down lyrics, and then my brother and I would pose for publicity photos. I would force my dad to take publicity photos of us.

I do remember that one time I got so frustrated with the lack of music that I forced my brother and some neighborhood kids to start a band with me, and we immediately had to record right away. So we went into my parents’ room and used their cassette boom box. I sang and played saxophone, which I was learning at the time, and another neighborhood kid played clarinet. My friend who had had one guitar lesson played guitar, and my brother played drums on Tupperware and pots and pans. We made a recording and named the band Heat Seeker.

AVC: Post-Heat Seeker, when did you start getting serious about music?

WS: I had always wanted to be involved in the arts in some way, but my understanding of what that meant was incredibly amorphous. I went through a phase in high school where I got a little more pretentious—wanting to be an important film director with an eye patch in one eye, a monocle in the other, maybe a canvas chair. Then I went though a phase of wanting to be a painter. The funny thing about all of that is that I didn’t realize those jobs were real. When I went away to college, surprisingly, I felt a tremendous amount of pressure to get a real job. I had never known any artists when I was growing up, so it didn’t occur to me that it was a real thing. I knew that Michael Jackson and Madonna existed, but I couldn’t make that transition into making it a real thing. It took me until college, when I suddenly had a nervous breakdown and I realized I wouldn’t be happy unless I did something creative. It wasn’t a luxury, and it wasn’t a lark. It was something I needed to do in order to escape despair.

I remember completely freaking out, and calling my parents and saying, “Listen, I’m not going to get a real job. I’m not going to train for a real job. I’m going to have to do what I always really wanted to do.” It was scary for them. They used to be really, really worried about me. So I went down to Austin and just crashed on a floor with five guys living in a house, like the way you do when you’re in your early 20s. I figured, “God, if I really fuck this up enough, I can probably scrape some kind of recovery in the second half of my 20s.” Fortunately, by the time that happened, the band was doing okay enough that I felt I could keep going.

AVC: What were Okkervil’s first shows like?

WS: Okkvervil River’s very, very first show was an open mic night. We got so sick of not having a show that we went to the Cactus Cafe in Austin, and brought all of our gear. We played a full-band set, and people were so mad at us. Our second show was one of those shows where they give you a bunch of free tickets to get your friends in because they figure, even if it’s a total loss, maybe your friends will buy some drinks. Our third show was for some friends of ours who got married very young, and we played at their wedding. I remember all the parents being really consternated about us being the entertainment. Our fourth show, I think, we played some weird thing at a bookstore, like an underground, alternative bookstore, the kind that used to exist for a split-second.

AVC: Did you have a firm idea of the kind of songwriter you wanted to be in those days?

WS: I didn’t really have a firm idea. I always wanted to be a band like The Beatles or Big Star, where there were multiple songwriters. My friends and I had a band in high school where we all wrote songs, and when I started Okkervil River, it was those same friends. I tried to force them to write songs again, and I was really, really shrill about it. But in the end, I couldn’t force people to write songs, and I couldn’t force them to sing. And I became the head of the band almost by default.

It’s funny. You start thinking about a bunch of different things that you could do, and then over time you start to narrow in on a very definite thing that you could do. And then, later on, you re-broaden, and suddenly you start to include some of that stuff again.

AVC: With I Am Very Far, it seems you’re in that re-broadening phase.

WS: I think you’re always in a re-broadening phase. I think every record is an opportunity to open up what you do even more. I think that really great artists and bands often start by very narrowly defining their palettes. That was a real revelation for me when I got to Black Sheep Boy. In the past, there were themes that ran through the records, and there were instrumental approaches that I took. But on Black Sheep Boy, I clamped down on a very small collection of ideas, instruments, and even colors in the artwork. I remember early on in Okkervil, I really liked witty songwriting. I really liked songwriting that had a worldly, ironic sense of humor to it. I remember also liking songwriting that had a severity to it, and a seriousness to it. And I remember thinking that those things couldn’t exist together, and that I couldn’t be a songwriter with the urbanity like I had hoped to be. I had to focus on being a serious songwriter. Over time, I realized I could combine those two things, but early on, it was hard for me to figure out how to reconcile them.

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