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At first, Kehinde Wiley’s art appears conspicuously populist. Or crassly commercial. Or maybe just plain tacky. The 28-year-old Los Angeles– born, New York– based artist is known for painting portraits of young African-American males in the manner of old European masters—and not in sober chiaroscuro, either. Instead, Wiley renders his models’ carefully chosen street clothes in designer pinks, baby blues, and fuzzy-chick yellows, projecting a vibe of grandmotherly kitsch rather than gangsta menace. His figures emerge from richly patterned grounds of curlicues and florals, assuming the beatific poses of saints and martyrs. Slickly illustrative and loaded with symbological significance, his pieces seem like a hipper spin on that dorm-room standby, the Michael Parkes poster.

Last year, Wiley brought this sensibility to a certain car maker’s African-American-targeted marketing campaign, Infiniti in Black. In turn, Infiniti sponsored the Brooklyn Museum’s recent mounting of Wiley’s first solo museum show, “Passing/Posing.” (According to the auto manufacturer’s thickheaded press-release copy, the “exhibit…display[ed] a wide range of art from French Rococo to contemporary hip-hop culture.”) He’s also racked up many high-profile sales to celebrity collectors, including Russell Simmons and Denzel Washington. For his part, Wiley is perfectly forthright and apparently unconcerned about his commercial connections and appeal. As he once stated in an interview, “We live in an age where the distinctions between high art and popular culture are finally starting to melt. Thank God. In a sense, that’s the strength of my work.”

As it turns out, it is. Wiley’s art is all about the erosion of such differences—between past tradition and present moment, masculine display and effete decoration, Fragonard and FUBU. And despite their clear legibility of construction and clean assuredness of intent, his portraits ultimately leave the viewer puzzling. In fact, the more time one spends in front of one of the three paintings and handful of studies hanging in “White,” Wiley’s current show at Conner Contemporary Art, the less easy gratification—or even clear, untroubled understanding—seems within reach. The result is a body of work that’s easy enough to describe but much more difficult to explain.

Take, for example, St. John the Baptist (2005). At 6 feet high, it’s an imposing image. The left-hand side of the canvas is filled with a three-quarters view of a lean, muscular African-American male in a sheer white do-rag, a white tank top, pale-blue jeans, and a gleaming, oversized silver belt buckle emblazoned with the name Romeo. The subject’s eyes are tightly closed, apparently fixed on some interior vision; he suspends his hands in midair with the mannered grace of any Renaissance holy man. His brown skin is perfectly smooth, reduced to a sensuous, light-reflecting surface. It’s a weird combo: Buff, streamlined muscularity is paired with immaculate clothing and delicate hand gestures, making the figure look like a contemporary urban superhero as imagined by Paul Cadmus during a fit of Christian ecstasy.

In Wiley’s color choices and paint handling, his equation of classicism and comic books is particularly evident. Tints and shades of chocolate brown are played off an icy range of pale silvery-blues and grays; an orange stripe down the subject’s pant leg offers one lone note of vibrant color. This narrowly controlled handful of hues mirrors academic painting of any number of centuries, in which light, shadow, and line did most of the work and color was pointedly reduced. Yet unlike, say, a lushly painted portrait by Ingres, St. John looks, well, plastic; it’s almost hard to believe that Wiley uses oils, not acrylics. There is no slow accumulation of glazed transparent layers here—only the flat immediacy proper to commercial illustration. The rapid facility of comic art and the relentless deliberation of neoclassicism are both meant to telegraph artistic mastery, and Wiley has apparently decided to reference them interchangeably.

The figure’s pose is actually borrowed from two panels—one of St. Peter, the other of John the Baptist—of the Griffoni polyptych, painted by Francesco del Cossa around 1473. In Wiley’s image, Peter’s slightly lowered face and closed eyes have been married to the Baptist’s arms, one of which holds a staff. In the original panel, the staff is a weatherbeaten wooden rod topped with a sculptural lamb, which itself is enclosed in a circular wooden halo. In Wiley’s painting, the staff is gleaming chrome, and the ringed lamb looks like an appropriated hood ornament. The pose and the original works from which it’s borrowed might be obscure to all but art-history wonks, but the religious signifiers—the lamb, the halo, the staff—are universally recognizable.

And then there are the patterns. In nearly every one of Wiley’s paintings, a busy, ornate, flat ground encloses and partially overlaps the figure. In St. John, an abstracted interlocking grid of metallic crosses and flowers in washed-out silver and blue ties the figure into the picture’s space. The decorations might be a shimmering art-nouveau design or a rococo palace wall—or just an endless sea of bling. All of these readings are suggested, yet none is by itself satisfactory. In St. Laurence (2005), the ornamental backdrop glows in a range of hot pinks—so much so that the model’s face bears the color’s reflected sheen. His clothing—a Champion jersey, shorts, and a bandanna—has all been rendered in perfectly coordinated shades of lilac and set off by two complementary pale-yellow bracelets. There’s a picked-out particularity to his features, sure, but even more so in the logos and labels on his clothes.

Perhaps less significant than the similarities Wiley manages to find between contemporary hiphop and classical European culture, however, is the artist’s apparent skepticism regarding both. Obviously, Wiley can’t help but eye European art with a certain amount of dubiousness. Early on, the artist emulated the works of 18th- and 19th-century British masters—Reynolds, Gainsborough, Constable—but as a young African-American, he was never able to identify with them in any satisfactory way. As he states in a 2002 show catalog: “Since I felt somewhat removed from the imagery, personally and culturally, I had a scientific approach and aesthetic fascination with the paintings. That distance gave me a removed freedom.”

But Wiley isn’t merely reconfiguring European art to African-American ends. Take his frames, for example: Each of the paintings in the current show is presented in a massive, excessively ornamented molding—but instead of being gilt, each frame is painted a stark matte white. Yes, the color matches the sterile whiteness of any modern gallery space, but it also causes the paintings to resemble the worst wannabe-grand home décor imaginable. Imagine scalloped white porcelain photo frames on the mantel—bracketing, say, a sculptural pair of praying hands. For Wiley, it seems, status symbols and brand names of any stripe are necessarily tacky (and eventually meaningless), no matter what culture they originated in—or, for that matter, what auto manufacturer riveted them together.

Wiley drives the point home with his feminized portrayal of playa masculinity. In the Tiepolo-inspired Madonna of the Rosary (2005), a towering male figure with a clean-shaven head purses his lips; with his head tilted back, he peers menacingly down at the viewer. He wears a snowy-white fur jacket; his pants and T-shirt are sewn from impeccable satiny fabrics. A silver rosary is delicately pinched between his soft index finger and thumb; a ring on his daintily extended pinkie glows, exuding an acidic lime color like an exotic bug and contrasting with the dull olive screen of the cell phone clipped casually to his waistband. The busy pale-blue ground of floral curlicues passes in front of the figure to climb gently up his inseam toward his crotch—just like the plumage that inches up a softly androgynous David’s thigh in a famous sculpture by Donatello. Here, symbols of prosperity become effeminate or downright campy; subjects one might expect to bristle with overdetermined machismo are transformed into drag queens.

Wiley is hardly the only African-American artist to appropriate of the devices of European art. In fact, he’s part of a new generation of black painters who have taken up the brush in a dialogue with dead white men. Kerry James Marshall, for example, has paired the compositional organization typically employed by baroque history painters with imagery drawn from racist illustrations of African-Americans from the early 20th century. Michael Ray Charles also uses the language of racist commercial art—say, images of Aunt Jemima—

combining them with references to everything from Picasso to Elvis. Despite their sometimes humorous jabs, both of these artists make essentially earnest paintings.

Wiley seems alone in his self-critical unwillingness to be sentimental—which makes his commercial success look increasingly improbable. The elements that enthusiasts happily recognize in his paintings are really being sent up or subverted at every turn. His work might even be a bit of a rebuke to earlier black artists such as Romare Bearden, who basically put an African-American stamp on the decorative impulses of European modernism. Wiley isn’t calling for a space at the table of classical civ to be cleared for black folks, nor is he trying to elevate black culture. He’s staring unflinchingly into the nature of all forms of posturing.

The tendency of much postmodern art has been to reject old hierarchies by making artistic activity more conceptual, less dependent on any one ancient medium’s troubled history. Wiley shows us that sometimes the most radical act is to continue with the seemingly insupportable. In doing so, he challenges our conceptions not only of art history, but also of gender, race, and even class—in short, of life as it’s lived. And that’s something only great art manages to pull off.CP