This dissertation focuses specifically on dancer Katherine Dunham (1909-2006), pianist Hazel Scott (1920-1981), cartoonist Jackie Ormes (1911-1985), singer Lena Horne (1917-2010), and graphic artist, painter, and sculptor Elizabeth Catlett (1915-2012). It explores the artistic, performative, and political resistance deployed by these five African-American women activists, artists, and performers in the period between 1937 and 1957. The principal form of resistance employed by these women was cultural resistance. Using a mixture of archival research, first person interview, biography, as well as other primary and secondary sources, I explore how these women constructed personas, representations, and media images of African-American women to challenge the racialized, reductive constructions found in mainstream white media and fine art outlets. They simultaneously engaged in “off the page” and “off the stage” political activism during eras that were pivotal within the African-American fight for freedom and equality. The primary purpose of the dissertation then is to unveil this multi-terrain struggle over Black female agency, equality, image, and representation waged by highly visible African-American artists and performers positioned in popular culture and fine art during this period. I argue that this battle is a fundamental component and sits within the larger long struggle for African-American freedom and equality.