Ten years ago Will Sheff was living in a shed with tin walls outside the Austin airport. At night, his roommates were various rodents until the sun rose and his bandmates came back. That shack was the studio where he and Okkervil River recorded their third album, Black Sheep Boy.
It’s the tenth anniversary of the record’s release, and Sheff has been revisiting that time in his life. Black Sheep Boy is getting a deluxe reissue and the band is preparing for a three-night run at the Bowery Ballroom, where they will be playing the album in full along with rarities written during that time period. Reaching back that far in his memory is bringing up some not-so-excellent times in the artist’s development: Sheff had a difficult go recording the band’s second record, Down the River of Golden Dreams, as the engineer seemed to “get off on not helping” and Sheff dealt with his own self-doubt. “I can’t hear that record without hearing a guy who’s in over his head and is scared and doesn’t know what to do,” he says between sips of herbal raspberry iced tea at Williamsburg’s Cafe Colette. “I had no idea if anything I was doing was any good.”
However Sheff felt about the record, it did well enough to inspire a lengthy tour in support of it, which brought about a personality shift for the band. Okkervil River’s members went from being more “bookish” to more “hard drinking, party” guys, and that eventually lead to the band breaking up, which eventually lead to Sheff sleeping in the Austin shed/studio. Sheff knew he needed to make some major life decisions.
“By the time we went in to make Black Sheep Boy I was sitting on a lot of stuff,” he says. “I was running out of money and had no real indication that anyone was interested in the work I was doing and had no real stability in my life. I thought that I’d make the record and see what happens, but it could definitely [have been] be the last one for me.”
As he and his label, Jagjaguwar, started sifting through things written around the album’s release for the reissue, Sheff happened upon a journal he was keeping during recording and realized that he was carrying a flicker of hope during that trying time.
“Reading that journal, I did see that I was incredibly unhappy back then, but there are also entries where I would write to myself, like, ‘Will, you will be OK. You just need to get through this. That was finally a good feeling,” he recalls.
When Black Sheep Boy was released, it was met with the same kind of tepid response that Sheff had shouldered after his first two albums, but it still wasn’t time to toss it. Shortly following Black Sheep Boy’s debut, Sheff was reading Magnet and came upon a Decembrists profile. He thought, “These guys seem to be doing the same kind of thing we are but are way more popular.” So he wrote Decembrists frontman Colin Meloy a letter asking if they would consider taking Okkervil on tour with them.
“I actually had never heard them, but wrote this letter saying I loved the record and asking if they’d please take us on tour. To Colin’s credit, he said yes,” Sheff says. “I can’t imagine doing that today. Like, me writing Grimes and asking ‘Pretty please take us on tour?!’” The opening slot on the Decembrists tour awarded the band and the Black Sheep Boy tunes a wider audience but the recognition from the wider indie rock listening community came from a New York Times article written by Kelefa Sennah praising the record. The record that could’ve ended Okkervil River launched them into indie rock notoriety, and their popularity has only grown from there.
Sitting in the cafe talking about that uncertain period in his career, Sheff he has no problem revisiting his former self. He’s even trying to get back in the mindset he was in when recording back then. Kind of.
“The music business is changing a lot right now, so in this weird way, I’m in the same boat I was ten years ago,” he explains. “At that moment in my life I had to throw out a lot of things and start over, and I’m back in that shape now, just rearranging and trying to adapt.” He cites the simplicity of the writing process for Black Sheep Boy as a guiding light for him right now as records and tries to be a successful musician in the present rock landscape.
“It’s time to live in reality and Black Sheep Boy helps me see that.”