To demonstrate the contested and complex nature of "black" music in the 1980s and 1990s—a time in which representations of blackness played an increasingly prominent role in U.S. popular culture—this dissertation comprises a series of four case studies exploring the work of various musicians in multiple genres. Analyzing the artistic strategies, discursive tensions, and historical legacies informing their work, each chapter treats black music as a cultural practice deeply embedded at the center of twentieth century life, including numerous racialized contexts. The first chapter documents the influence of Black nationalism and avant-garde jazz in the creative lives of Asian American jazz musicians, showing how, in the 1980s, they were inspired by the music of the 1960s to cultivate their own musical identities. The second chapter compares producer/rapper Dr. Dre's seminal album The Chronic (1993) to his work on gangsta rap group N.W.A.'s Straight Outta Compton (1988), exploring how the sound and imagery of gangsta rap responded to particular facets of Los Angeles's urban geography. The third chapter explores how soul singer D'Angelo opposes the male-centered materialism of mainstream rap music by offering listeners a reconstructed musical experience of Afro-Diasporic spirituality. The fourth and final chapter analyzes Eminem's use of parody as an artistic strategy for authenticating himself as a white rapper, revealing that his ironic performance of white identity provided a site where listeners could debate the continuing significance of whiteness vis-à-vis blackness. Like race itself, black music is a socially constructed phenomenon. Paying attention to its sounds, as well as the discourse surrounding it, grants us insight into how musicians, fans, and critics negotiate, and at times contest, issues of race and politics through music.