This dissertation theorizes a contemporary hip-hop genre that I call “neo-bohemian,” typified by rapper Kendrick Lamar and his collective, Black Hippy. I argue that, by reclaiming the origins of hipness as a set of hybridizing Black cultural responses to the experience of modernity, neo-bohemian rappers imagine and live out liberating ways of being beyond the West’s objectification and dehumanization of Blackness. In turn, I situate neo-bohemian hip-hop within a history of Black musical expression in the United States, Senegal, Mali, and South Africa to locate an “aesthetics of existence” in the African diaspora. By centering this aesthetics as a unifying component of these musical practices, I challenge top-down models of essential diasporic interconnection. Instead, I present diaspora as emerging primarily through comparable responses to experiences of paradigmatic racial violence, through which to imagine radical alternatives to our anti-Black global society. Overall, by rethinking the heuristic value of hipness as a musical and lived Black aesthetic, the project develops an innovative method for connecting the aesthetic and the social in music studies and Black studies, while offering original historical and musicological insights into Black metaphysics and studies of the African diaspora.