The second of three chapters on the power of chocolate cities, this chapter centers the lives, activism, and pioneering efforts of three black women professionals, entertainers, and community activists: Mary Hill Sanders, Dionne Warwick, and Alma Burrell. Exploring their lives, health setbacks, and push against the glass ceiling and racial oppression, the authors highlight their sophisticated and politically informed racial geography of the United States. Detailing the movement of black people throughout the domestic diaspora, this chapter illustrates the how gender, place, race, and power collided in the lives of black people before and after the civil rights movement.