This dissertation examines the post-1959 activism of Cuba's socially critical artists and intellectuals, and the effects of the Cuban state's institutionalization of culture. I analyze the Cuban underground hip-hop movement as a case study of the ways in which Black artists and intellectuals in Cuba have employed cultural aesthetics to challenge contemporary inequalities organized around race, class, gender, and sexuality. I address the social context in which the Cuban underground hip-hop movement emerged by linking it to Cuba's revolutionary project and to other counter-cultural social movements in Cuba's history and from other post-colonial contexts. Drawing upon extensive ethnographic, historical, and interview-based research, the study engages with existing theories of the state, culture, civil society and the public sphere, but also reveals their limitations, particularly when applied to non-European contexts. As such, the dissertation offers significant insights into the relations between politics and culture, hegemony and resistance, history and the imagination of a better future, both in Cuba and beyond.