When I think of Kehinde Wiley's paintings, a couple of affiliated effects come to mind. In his work we look at history juxtaposed with a really unstable relationship to realism. But I don't want to start an essay with quotations from history – after all, that's what Kehinde Wiley's paintings are already doing. The essential issue at hand is to give some context to portraiture, hip hop visuality, sampling, collage, and quotation. I want to unpack some of the issues that Wiley engages in his work.