From the 1930s to the present, women have played instrumental and visible leadership roles in the remarkable growth of African American gospel music. Through both creative and entrepreneurial activities, these women paved the way for the expansion of an emotive sacred music expression from the worship practices of southern migrants to audiences around the world. This dissertation focuses on the work of three cultural trailblazers, Mahalia Jackson, Aretha Franklin, and Karen Clark Sheard, who stand out in the development of gospel music as virtuosic vocalists and pivotal figures whose sonic imprints can be heard both in sacred songs performed in churches and in American popular music. By deploying exceptional musicality, a deep understanding of African American Christianity, and an embrace of commercialism, the three singers have conserved and reworked musical elements derived from an African American heritage into a powerful performance rhetoric. By using musical mastery, they have forged paths for gospel music as a commercial phenomena and a vehicle to transform discourses of race, gender, class, and religion. At the same time, they have managed other duties and responsibilities in their families, in their communities, and in the music industry, thus demonstrating that “greatness” in gospel music is the outcome of extraordinary skills and various interwoven forms of labor. Through the study of the musical lives of Jackson, Franklin, and Clark Sheard from an intergenerational perspective, this dissertation posits that they participate in making a feminist music culture that prioritizes spiritual authenticity and the commercialization of musical knowledge as a counter-hegemonic practice. Thus, their contributions should be first viewed as “cultural work,” a form of African American women’s activism that consciously advances a female musical perspective in the service of community furtherance. In broad terms, this exploration of women’s gospel music legacies elucidates the cultural, spiritual, and commercial processes that have shaped African American sacred music practices, and as such, it provides new insights into a creative domain which has produced the most influential vocal idiom in American popular music.