American artist Barkley L. Hendricks (1945–2017) revolutionized contemporary portraiture with his vivid depictions of Black subjects beginning in the late 1960s. This book contextualizes Hendricks’s portraits at different stages of the country’s history and places him in the pantheon of innovative twentieth-century artists. Hendricks developed his signature style at a time of significant social and cultural change in the United States, especially with regard to Black artists, and amid a perceived bifurcation between abstraction and representation. He produced portraits from the late 1960s through the early 1980s. Following a hiatus during which he made landscapes, basketball paintings, works on paper, and photographs, he resumed his portraiture practice from 2002 until his death in 2017. Hendricks’s portrait paintings, often derived from photographs of friends and family, hired models, or figures he encountered on the street, were inspired by the artist’s research, international travels, and visits to museums like The Frick Collection, where he studied centuries-old European paintings by artists such as Rembrandt, Van Dyck, Bronzino, and others. This publication presents some of the most inventive and striking examples from Hendricks’s first period of portrait painting, including “limited-palette” canvases—featuring Black figures dressed in white against white backgrounds—a self-portrait, and boldly colorful works that spotlight their subjects’ spectacular styles and poses. An assessment of this great artist acknowledges his significant contributions to the canon of American art and portraiture in general. In the book, Hendricks’s art and its impact are explored by artists and creative figures including Derrick Adams, Hilton Als, Nick Cave, Awol Erizku, Rashid Johnson, Fahamu Pecou, Mickalene Thomas, and Kehinde Wiley.