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Sep 02, 2008 By J. Pace Photography by Ryan Bakerink Okkervil River

Okkervil River singer/guitarist Will Sheff is having more fun these days. Before 2005’s Black Sheep Boy charmed critics, he was seriously contemplating throwing in the towel. “Basically, I was broke,” he says from his home in Brooklyn. “I was totally broke, and I’d been broke for my entire adult life.”

Sheff was also watching his relationships erode while he spent most of his time on tour. As in any overblown rock biopic, you can’t have the artist without the anguish, and Sheff often finds himself painted as the uber-emo tortured soul. “I was really fighting, after Black Sheep Boy came out, to dispel this idea that I was a tormented, doom-and-gloom kinda guy,” he says. “I was always a person with a sense of humor, and I think I enjoy life, you know? I think that record was just kind of dark.”

Since the success of Black Sheep Boy and the breathing room it gave the band, things have lightened up considerably. Sheff and his bandmates—Scott Brackett (trumpet/keys), Brian Cassidy (vocals/guitar/mandolin), Travis Nelsen (drums), Patrick Pestorius (bass), and Seth Warren (electronics)—have confidently stirred more and more pop elements into their emotive and once-basic folk-rock, each album boasting more instrumental augmentations like horn and string sections, along with an increasing barrage of pop culture references. For 2007’s The Stage Names, and now The Stand Ins, the use of those ingredients became a mission statement. “I think when you hear The Stage Names you hear me painting with those colors for the first time,” says Sheff. “But when you hear The Stand Ins, you hear me knowing how to use them a lot better.”

The Stand Ins sprang from the same recording sessions as The Stage Names, and with it we have another filmic gamble: the sequel. “It’s the sequel to the record,” says Sheff. “Sequels are never as good—that’s a truism that everyone knows. I mean, the sequel is never as good as the original, at least when you’re talking about movies. So when you’re doing something like that, you’re courting failure right from the very beginning….A lot of these things are intimidating to me, but basically it just felt very right, and that was the reason we decided to go ahead and put it out as a followup. It felt right.”

With The Stand Ins, Sheff takes up right where he left off. The songs remain littered with a cast of groupies and burnt-out road hogs, their lives failing to match their grandiose cinematic ideals, while Sheff’s lyrics continue to take satirical stabs at rock-and-roll mythology.

The knowingly saccharine “Pop Lie” frames its exploration of pop’s fickle artifice in pop’s own fickle framework: cheeky synth lines and guitar hooks. “We were really yukking it up when we were making that song,” says Sheff. “That song is kind of like when it’s Halloween and you eat all your candy in one night, then throw up. That was kind of the approach we were taking production-wise.”

“Singer Songwriter” is a send-up of the privileged life that often accompanies indie rock. “There’s an aspect of indie rock that so ties into yuppie lifestyle porn. You know: iPhones, hybrid cars, iPods, lofts, stuff like that,” says Sheff. “You sort of start to realize that indie rock, as things go, is not the most revolutionary, politically incendiary, world-remaking genre. It’s pretty affirming of how things already are. It’s in line with The Eagles as opposed to The Sex Pistols.”

For Sheff, indie rock’s posturing is exactly what makes it fertile ground for wry contemplation. As a result, people inevitably dig for autobiography in his words, counting his heartfelt delivery as pure confessional, grabbing at lyrical clues to prop up their own fictions; portraits of the artist. But while Sheff borrows liberally from what he knows, namely life in a popular indie rock band, his narrators are just characters (if not caricatures). He’d be the first to dismiss his own biopic.

“People take artists, and the sort of hagiographic worshipping of artists very seriously,” he says. “Musicians are idiots. They’re Cro-Magnons on drugs with guitars. I think that people need to be made fun of, and not taken so seriously. Myself first and foremost.”