Approximately ten minutes into my interview with Will Sheff, all of my best-laid plans are thrown out the window. I’m talking to him about Okkervil River’s highly lauded 2005 album Black Sheep Boy, and how he presumably had his life changed by that album’s success. Black Sheep Boy vaulted Okkervil River onto the national stage after seven or so years of false starts and burgeoning breakouts, and it seems reasonable to surmise that that success changed him. I’m assuming that he has grown comfortable as a humble touring musician, enjoying the coast that comes after the rollercoaster ride of success.
But when I ask him how his life is different now, he responds exactly how I don’t expect: “I think I’m in a similar place.” After all of these years of touring the world, making records with Roky Erickson and nearly making another with Lou Reed, Sheff is back at square one. “There are points in your life…where you go ‘Fuck, I just want to say goodbye to everything that came before this. I’m going to put it away in a box and I’m going to be a different person now. I’d like to lay to rest the previous me and become the next me.’” Will Sheff is right where he was ten years ago.
Back in 2004 and 2005, Sheff thought that Black Sheep Boy was probably going to be his last record. Down the River of Golden Dreams, Okkervil River’s well-received second proper album, didn’t exactly change the band’s fortunes. Sheff found himself confronting financial failure. The lead-up to Black Sheep Boy was, as Sheff puts it on the phone from his home, “a really, really scrappy time.” He was touring more than ever, crashing in guest rooms and practice spaces when he wasn’t on the road—and even then he was splitting time between Austin, Texas, his adopted home, and Bloomington, Indiana, the home of his label (and a tumultuous on-again, off-again relationship). Sheff describes his view of the band’s impending doom as a “when” and not an “if” scenario. Going into Black Sheep Boy, “I wasn’t really thinking ‘I hope I’ll save my career,’” he says. “I was thinking, ‘At least I’ll have made a good record.’” Black Sheep Boy wasn’t going to be a last-ditch effort. It was going to be the last effort, full stop.
Black Sheep Boy wasn’t going to be a last-ditch effort. It was going to be the last effort, full stop.
The Will Sheff of today feels much the same way. Nowadays, even a band that produced a run of albums like Black Sheep Boy, 2007’s The Stage Names and 2008’s The Stand Ins can’t catch a break. “These days I’m like, ‘Will I make one more record, will I make two more, will I make three more, will I make zero more?’” he says. Bands of Okkervil’s caliber face a different musical economy now than they did even a decade ago. “Back when I was doing Black Sheep Boy, my career felt like it was falling apart,” Shelf says. “Now it feels different, it feels like everyone’s career is falling apart.”
We talk about how the economics of being in a working band—what is often an endless ouroboros of touring, promoting, writing, touring, promoting—can devour artistic ambitions. “I long for the ’60s model, where you make a record in a week and then you tour on it and you make another one six months later.” The pace of the industry today requires artists to essentially do every facet of their job at the same time and to tour for years on a single release. Indeed, when I call Sheff, he can barely tear himself away from working on recreating samples for the string of shows Okkervil have planned around the Black Sheep Boy reissue, which is out this week.
As Sheff describes it, the nexus of good fortune and better timing allowed Okkervil River to become the working entity that it did. “What changed when I made Black Sheep Boy was that, suddenly, I could actually quit my job,” Sheff recalls. “I was actually making money off of record sales.” That model of the music industry—the one in effect just ten years ago—doesn’t apply to today’s economy. “It’s kind of thrilling, because you’re sort of like ‘Who gives a fuck anymore?’” Sheff laughs the situation off, saying that “there’s no brass ring to grab.” The disappearance of any sort of safety net strikes Sheff as an opportunity to cast anew.
Shedding former selves figures heavily into Black Sheep Boy. The album, a meditation on Tim Hardin’s folk song about a tragic heroin relapse, obsesses over the curses of family, tragic flaws, and plain old bad luck. Jagjaguwar, the band’s longtime label, put out the collection of songs in 2005, and by some twist of luck, some divine intervention, or maybe because it was just that good, the album caught fire.
Small things have changed since then. As you might expect, Sheff has aged out of a few traditional “rock” habits. He drinks less, for one. “You know what else has changed?” he says, preempting embarrassment. “I hate to admit it, [but] I’m a lot nicer to people who work at the clubs.” His voice carries the tinge of an elementary schooler fessing up to splattering the bathroom with wet toilet paper. “I was a shit sometimes,” he admits, “but mostly I wasn’t a shit.”
So maybe Will Sheff is ready to rip it all up and start over again. I had planned on talking through the pressures of staying successful with Sheff, but he insists that “if I start to think ‘Shit, this record better sell,” then I’m lost.” Plans are made to be ruined. Thumbing through the liner notes for Black Sheep Boy, one section sticks out: The lyrics for “The Latest Toughs” contain four blank lines for the reader to add in their own words. Sheff has planned to rewrite everything from the beginning. This was the plan all along. FL
