Photo: Matthew Niederhauser/Institute

In a soaring studio on the outskirts of Beijing, where Kehinde Wiley came in 2006 to set up the first of his several global production outposts, the 35-year-old painter is showing off his women. Most of them are still incomplete—their faces need touching up, their gowns (custom-designed for his models by Givenchy) lack texture. But one already stands out: a tall, elegant black woman in a long blue dress—the canvas is enormous, eight feet by ten feet—calmly staring down the viewer. In one hand, she holds a knife. In the other, a cleanly severed brunette female head. “It’s sort of a play on the ‘kill whitey’ thing,” Wiley says.

Subtle, I think. Not that Wiley’s work ever seems that subtle at first. Best known for his oversize portraits of young African-American men he finds on the street—“the boys,” he calls them—against florid wallpaperlike backdrops in poses lifted from old portraits of European gentry, Wiley has in a mere decade built a monster career around bright colors, big ideas, and a canvas the size of Earth itself, every person in every nation a potential subject. His series “The World Stage” makes that promise literal, as he globetrots from the favelas of Rio to the slums of Delhi, pulling charismatic-looking men into the studio for Renaissance-style tribute. And his newest portraits, for a show opening May 5 at Sean Kelly Gallery, constitute his first all-female exhibition and tackle no less grand a theme than the historic representation of women in art.

That unabashed bombast has made Wiley a walking superlative: the most successful black artist since Basquiat, possibly the wealthiest painter of his generation, certainly the one who made his name earliest (he was 26 for his first major solo show), a gay man who has become the great painter of machismo for the swag era, a bootstrapper from South Central who talks like a Yale professor (much of the time), a genius self-­promoter who’s managed to have it both ways in an art world that loves having its critical cake and eating the spectacle of it, too, and a crossover phenomenon who is at once the hip-hop world’s favorite fine artist (Spike Lee and LL Cool J own pieces) and the gallery world’s most popular hip-hop ambassador. Not to mention an all-around positive guy.

“Women have always been decorative,” Wiley says, gesturing at the portraits around him. ‘They’ve never been actors or possessed real agency.” Compact, with a pink dress shirt tugging at itself across his chest and an unself-conscious gap-toothed grin, he doesn’t look like the grave, hoodie-rocking men he often portrays so much as their nerdy cousin. (He listens to NPR on his Beats headphones.) Despite seeming exhausted, he’s affable and reflective, as if picking up where he left off in some past interview.

Which brings us back to the lady with the severed head. Like most Wiley paintings, this one has a backstory: Her name is Triesha Lowe, Wiley explains. She’s a stay-at-home mom whom Wiley found at the Fulton Mall. Her pose is a riff on classical depictions by Caravaggio and Gentileschi, of the biblical story of Judith beheading Holofernes. And the severed head? “She’s one of my assistants.”

There’s nothing new about artists using assistants—everyone from Michelangelo to Jeff Koons has employed teams of helpers, with varying degrees of irony and pride—but Wiley gets uncomfortable discussing the subject. “I’m sensitive to it,” he says. When I first arrived at his Beijing studio, the assistants had left, and he made me delete the iPhone snapshots I’d taken of the empty space. It’s not that he wants people to believe every brushstroke is his, he says. That they aren’t is public ­knowledge. It’s just a question of boundaries. “I don’t want you to know every aspect of where my hand starts and ends, or how many layers go underneath the skin, or how I got that glow to happen,” he says. “It’s the secret sauce! Get out of my kitchen!”

Producing work in China cuts costs, but not as much as it used to, Wiley says. These days in Beijing he employs anywhere from four to ten workers, depending on the urgency, plus a studio manager, the American artist Ain Cocke. The Beijing studio began as a lark: After visiting an artist friend there and liking what he saw, he and a couple of his New York staffers flew out, rented some space, and started painting, “sort of like a retreat,” he says. One thing led to another—“another” being a five-year relationship with a Chinese D.J.—and eventually the Beijing studio became the main production hub as well as his second home. He recently bought an apartment overlooking Chaoyang Park, complete with a live-in maid and two miniature greyhounds, Xiaohui, or “Little Gray,” and Celie, named after the character in The Color Purple.

Photo: Courtesy of Kehinde Wiley and Sean Kelly Gallery, New York

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.

He attended the Los Angeles County High School for the Arts and then the San Francisco Art Institute. He took cooking classes, too, since he knew painting likely wouldn’t support him. “I thought I’d be a chef by night and paint by day,” he says. “Now I just have fabulous dinner parties.” The Yale School of Art pushed his thinking. There, Wiley devoured the whole academic buffet—art theory, world history, identity and cultural theory.

The question of identity wasn’t just academic. His father, Isiah Obot, had come from Nigeria in the seventies and studied architecture at UCLA, where he met Wiley’s mother. He left before Wiley was born, and Wiley’s mother destroyed all her pictures of him. “I always wanted to know what he looked like,” Wiley says. “As a portraitist, I was obsessed with his face.” (The name Wiley comes from his mother’s first husband.) When Wiley was 20, he raised $700 from family members, hopped a plane to Nigeria, and started searching. Knowing nothing more than his father’s name and expertise, he traveled to Akwa Ibom, the state in southern Nigeria where his father’s tribe originated, went to the state capital of Uyo, learned his father was working at a nearby university, and walked into the architecture department. “His name’s on the door,” Wiley says. “He’s the head of the department.”

It was awkward. “He didn’t understand my intention at first. He probably thought I was there to shake him down,” Wiley says. His father had recently married and hadn’t told his wife about his far-flung progeny. “I fell into this deep depression afterward.” He painted a series of portraits of his father. He had videotaped the whole saga and watched it over and over.

That was also around the time Wiley came out. The inciting incident: His girlfriend at the time came out to him. “I was like, ‘Well, if you’re not playing this game, I’m not playing either,’ ” he says. His brother wasn’t surprised. His mother was just happy she had five other kids who could give her grandchildren. His sisters? “Total fag hags,” Wiley says. Was there any trouble at school? “Art school? San Francisco? Get the fuck out of here. The problem was if you were straight.”

After graduating from Yale, Wiley took a residency at the Studio Museum in Harlem. “One Hundred Twenty-fifth Street was so dense and packed with pageantry and peacocking,” he says. “I wanted to try and get that down in painting.” He started stopping men on the street and asking to paint their portraits. Eventually he and his subjects started talking about art history, and Wiley began painting their portraits based on their favorite classics.

He didn’t have one big break so much as a string of them. In 2002, a couple of high-profile exhibitions at the Studio Museum featured his paintings. Jeffrey Deitch took notice and offered him his first major solo show. Wiley was on an Italian Renaissance kick and had the idea of creating his own Sistine Chapel. The result was Faux/Real, which featured guys in modern hip-hop garb posing as saints in front of swarms of sperm, among other decorative patterns, while other men floated among clouds like thugged-out angels on a canvas sky hung across the ceiling.

In Rumors of War (2005), he transposed men into contexts of military glory. Down (2008) depicted dead and dying men on a massive scale, while Black Light (2009) used blown-up photos instead of painted figures. The World Stage takes mostly black and brown men from Brazil, Senegal, Nigeria, India, and Israel and sets them against a country-specific backdrop, such as Dutch wax-­resist fabrics.

His next gallery show, called “Mr. President,” will feature portraits of presidents of various African countries as they wish to be portrayed, he says, and will address “notions of taste and vulgarity.” Painting a powerful political figure is different from pulling a kid off the streets, of course. “It’s redundant, almost,” he says. But as Wiley sees it, it’s not his job to judge. “The games I’m playing have much more to do with using the language of power and the vocabulary of power to construct new sentences,” Wiley says. “It’s about pointing to empire and control and domination and misogyny and all those social ills in the work, but it’s not necessarily taking a position. Oftentimes it’s actually embodying it.”