In this talk, I examine how barbershop quartet singing functioned as a key battleground for debates over civil rights and racial segregation during the long civil rights era. Focusing on the international fraternal organization, the Society for the Preservation and Encouragement of Barber Shop Quartet Singing in America (SPEBSQSA) from its founding in 1938 to its desegregation in 1963, I recount the largely unknown and undocumented segregationist period of American barbershop music. Barbershop served as a unique site for civil rights discourses for several reasons: its status as a uniquely American art form (that, consequently, had to uphold American values and freedoms), its prominent use of the metaphor of “harmony” (musical, racial, and societal), and its reach across virtually all social strata the U.S. and Canada during the mid-twentieth century. Drawing upon previously unexamined archival and personal documents, this I offer a rare behind-the-scenes look at how fraternal organizations discussed matters of racial segregation behind closed doors. In doing so, I unearth the stories and voices of several Black barbershoppers who mobilized their presence as political action, which ultimately led to SPEBSQSA’s desegregation. What emerges is a history of music, race, and civil rights that sheds light both on purposefully buried Jim Crow–era racism and the agency of Black amateur musicians who shaped the history of U.S. civil rights activism and reform.