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By applying the visual vocabulary and conventions of glorification, wealth, prestige, and history to subject matter drawn from the urban fabric, Kehinde Wiley makes his subjects and their stylistic references juxtaposed inversions of each other, forcing ambiguity and provocative perplexity to pervade his imagery. As technically impressive as they are conceptually complex, Wiley's portraits feature young black men in classic heroic poses, destabilizing canonical ideas of white masculinity and power. In his related, ongoing “World Stage” series, Wiley’s heroic figures are depicted in front of colorful background patterns that make specific reference to textiles and decorative patterns of various cultures, from 19th-century Judaica paper cutouts to Martha Stewart’s interior color swatches. Wiley’s penchant for jarring juxtapositions stems from his desire to complicate notions of group identity.

In 2018 Wiley became the first African-American artist to paint an official U.S. Presidential portrait for the Smithsonian National Portrait Gallery. Former U.S.President Barack Obama selected Wiley for this honor. In 2019 the artist launched Black Rock Senegal, a non-profit artist-in-residence program located in Dakar, Senegal. That same year, Wiley debuted his first large-scale public sculpture in Times Square, New York, showcasing a young African American man astride a rearing horse. In 2020 Wiley received France’s distinction of Knight of the Order of Arts and Letters.