Kehinde Wiley masterfully borrows the language of Old Master portraiture to reframe art historical tropes of subject matter, power, and recognition in the context of race. His large-scale figurative paintings are equally as grand, ornate, and rich in symbolism as traditional portraiture; however, Wiley subverts the canon by depicting male protagonists of African descent, a demographic that has been virtually omitted from the Western painting tradition throughout the centuries.

Wiley's models typically wear everyday contemporary clothing—sweatshirts, jeans, sports jerseys—while enacting traditional roles seen in canonical portraiture such as the gallant equestrian or the stoic Christ figure. The artist initially approached young men on the streets of Harlem and convinced them to pose for him in his studio and recreate classical portraits. His approach has now expanded to embrace models (not all of them black) in cities around the world, from Jerusalem to Mumbai and Rio de Janeiro, as part of his ongoing World Stage series.