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6. Outsource to China

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Napoleon Leading the Army Over the Alps, 2005.  

And working in Beijing gives him a little space to breathe. “It’s distracting,” he says of my natural interest in finding out who did what. “I want the illusion of a fully formed object without seeing the mechanisms going on behind the curtain. That’s show business.”

He knows show business. VH1 commissioned a series of Wiley portraits of rap greats like Ice T for its 2005 Hip-Hop Honors. He worked with Puma to design shoes for the South Africa World Cup, the first such event held in Africa. And in 2009 he painted a commissioned portrait of Michael Jackson clad in armor atop a white horse, the King of Pop made literal. He and Jackson worked for months on the look and feel of the portrait. “We were talking about Rubens, and he wanted to know if it was late or early Rubens I was referencing.”

The spectacle is always carefully staged, particularly with “the boys,” which can sell for more than $100,000. “There are certain ground rules,” says Wiley. Eight to ten paintings per show. Men, usually. Street casting: Wiley goes out with a team to recruit young men as models. Back in the studio, they leaf through art-history books, and the subject gets to decide which old-style work he wants to be portrayed as. He poses for photos, and the photos become templates for full-size paintings, which Wiley produces with his assistants in New York, Dakar, and Beijing.

Or not. In many cases, Wiley acknowledges, none of that official process—the street casting, the selection of poses from art books, the painting based on those ­poses—happens at all. “The clothing, sometimes completely made up,” he says. “The models themselves, brought in from a fashion agency.” And in at least one case, the “boy” is in fact a girl. “Oftentimes, if there’s a show of ten paintings, four of them will be complete frauds.”

Wiley likes to keep his intentions ambiguous, comparing himself to the two-faced Nigerian trickster god Eshu. Does the decision to paint an anonymous black man (or Ice T) posing like Napoleon constitute an act of social justice that gives African-Americans their rightful place in the Western pantheon? Yes. Is it a mockery of the pantheon itself and anyone who would wish to be in or buy into it? That too. “As an artist and a student of history,” he says, “you have to be at once critical and complicit, to take a stance that says, ‘Yes, I’m in love with this magic, this way of painting, but damn it’s fucked up.’ ”

By embracing contradiction rather than running from it—by toggling between insider and outsider, art-history party-crasher and homage-payer, Serious Artist and practical jokester—Wiley has broadened his potential audience to include … everyone. (Everyone, that is, who doesn’t see the work as “dead and mechanical,” as the Times put it, or isn’t uncomfortable with his “market-friendliness,” as ­Artforum put it.) His paintings appeal to buyers interested in interrogating the social construct of portraiture, those who think it’s hilarious to put black dudes in do-rags on horses carrying scepters, and those who just miss the grand scale of history painting. Perhaps that explains his popularity beyond the Chelsea whirlpool: In addition to top collectors like Mera and Donald Rubell, Wiley counts Elton John, Lance Armstrong, Venus Williams, and Neil Patrick Harris among his buyers. Wiley isn’t merely many things to many people. He’s whatever you want him to be. Even if all you want is a big, badass military-style portrait to hang next to your gold records.

Of course, ambiguity is itself a stance, as he knows. “Painting does more than just point to things,” Wiley says. “The very act of pointing is a value statement.” He crosses his arms, pointing in opposite directions. “I’m just doing this sometimes.”

Wiley always knew he would be an artist. “I never had to choose,” he says. “It’s the only thing I’ve ever been any good at.”

We’re sitting in an impossibly fancy Mediterranean restaurant in Sanlitun Village, a commercial development in Beijing that barely existed four years ago. He’s wearing a dinner jacket and sampling an extensive cheese plate (trying to, at least—he’s lactose intolerant). “I love that you sense growth around you all the time, whether it be fashion or architecture or art or politics,” he says of living in China. “There’s still a sense of malleability.”

Wiley grew up in South Central Los Angeles, the fifth of six children raised by a single mother on welfare putting herself through grad school in linguistics. “I grew up in this weird, educationally elite but economically impoverished environment,” says Wiley. “Total Oprah story.”

When he was 11, his mom sent him and his fraternal (“Thank God—we’ve got enough issues as it is”) twin brother Taiwo to after-school art classes. In those days, Taiwo was the better artist. “It would piss me off how well he could draw,” says Wiley. But Wiley enjoyed it more and stuck with it.


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