Blackface minstrelsy, America’s first form of popular entertainment, was forged in the crucible of nineteenth-century slavery. Since then, the performance tradition has haunted the American popular entertainment industry, and we continue to grapple with its insidious afterlife and continuing musical, historical, cultural, and political resonances in our present day. In my research, I examine how Black women in the late nineteenth and early twentieth centuries negotiated the terms of musical performance in the wake of blackface minstrelsy. Guided by Black feminist frameworks, I explore how these artists shaped the look and sound of American popular entertainment through critical, transformative, and subversive performances of blackface tropes. I hope that this work will offer us new ways of understanding Black female performance practices and shed light on the complexities and contradictions within American popular culture.