“The master’s tools,” wrote the poet Audre Lorde, “will never dismantle the master’s house.” “Isn’t life a series of images that change as they repeat themselves?” asked Andy Warhol. If the master’s tools are portraits of kings, saints, and ornamental women garbed in the ermine and satin of their class; and if the corridors of power link the master’s house to the museum, where grand white men are shown making decisions and alluring white women signify the things decided; and if those portraits are repeated with young black men from the Fulton Mall in downtown Brooklyn standing in the place of Giovanni Bellini’s St. Francis in the Desert, ca. 1480, or Anthony van Dyck’s Roi à la Chasse, 1635, or John Singer Sargent’s Countess of Rocksavage, 1922—if, that is, ermine has changed into Adidas, girls have changed into boys, white has changed into black, and the only things consistent are diamond earrings and a heady mix of sexual exposure and narcissistic puissance—then what kinds of politics, pleasure, and dismantled image-series do we see?

Kehinde Wiley has made such images since 2001, and until this show they were paintings. At monumental size, his oils posit their subjects as gods and princes, draped in logo-rich hoodies, dripping with bling and crowned with perfectly uncreased baseball caps, back-dropped by floral and geometric motifs that swirl across their bodies and suture them into the viscous handmade surface of the painting. This, too, has changed. The histrionic postures and fabulous streetwear still pertain, but the works on view here selected from Wiley’s 2008–2009 “Black Light” series were seventeen digitally manipulated photographs, each measuring just over two by three feet (all works 2009). The eighteenth photograph of the show depicts a muscled young man on a white-draped plinth, swooning like the dead Christ and spritzed with droplets like a Calvin Klein underwear model. No swirls damask his background, but viewers who remember Wiley’s show at Deitch last year will recognize the photo as a study for an enormous painting titled Sleep, 2008, after Jean-Bernard Restout’s Sleep, ca. 1771. “Black Light,” in fact, grew out of the working photos that Wiley shoots of his models, whom he approaches first in public places and who select their poses by paging through art-history books in his studio. Saturated in a hot, caressing light and enlivened with the computerized addition of the patterns—adapted from 1950s wallpaper and Martha Stewart’s home-decor collection—the photographic studies have become pieces in their own right.

There are two intertwining problems with this. First is that the radically reduced scale cheapens the sitters’ gravitas. The photographs cannot command the visitor’s experience of space, and so the immediate physicality of their power—as distinct from the mannered tropes by which it is expressed—dissipates. Second is that paintings are fantasy objects made by direct touch, while photographs (even digitally altered ones) are realist objects made at a mechanized distance. Fantasy and touch also constitute Wiley’s conceptual project as a painter. His flesh-and-blood everymen, recruited off the street like so many hookers or soldiers and transposed into paint like royalty, become ciphers for an apotheosis part African, part European, all American, totally historical, completely contemporary, discernibly real, undeniably made-up, and uncertainly masculine. In the photographs, this overdetermination empties; these guys look fey and stylish, but not like masters of culture repeated and transformed.

Consider, nevertheless, the voluptuous baby face and suspicious beard of the kid wearing camouflage in After George Romney’s Elizabeth Warren as Hebe. Now check the exhibition catalogue, which lists the sitters’ names. S/he is the artist Mickalene Thomas—i.e., an insider black woman playing an outsider black boy playing an aristo white woman playing a goddess. The contested body torques another turn. . . .

—Frances Richard