For most of Kehinde Wiley’s very successful career, he has created large, vibrant, highly patterned paintings of young African American men wearing the latest in hip hop street fashion. The theatrical poses and objects in the portraits are based on well-known images of powerful figures drawn from seventeenth- through nineteenth-century Western art. Pictorially, Wiley gives the authority of those historical sitters to his twenty-first-century subjects. In 2005, VH1 commissioned Wiley to paint portraits of the honorees for that year’s Hip Hop Honors program. Turning his aesthetic on end, he used his trademark references to older portraits to add legitimacy to paintings of this generation’s already powerful musical talents. In Wiley’s hands, Ice T channels Napoleon, and Grandmaster Flash and the Furious Five take on a seventeenth-century Dutch civic guard company.