Diversión contends that our understanding of the Cuban diaspora is lacking not in seriousness, but in play. Against the melancholia, anger, and pain that have defined dominant characterizations of Cuban America, Laguna provides an affective complement for understanding this community by insisting on the centrality of ludic popular culture for a diaspora that has completely transformed in the last twenty-five years. The majority of Cuban America is now made up of arrivals since the 1990s and the US-born generation—two segments that have received little attention in cultural studies scholarship. Diversión examines these generational shifts and tensions through readings of a wide range of playful popular culture forms originating in Miami and Cuba from the 1970s through the 2010s. These include the standup of comedians like Guillermo Alvarez Guedes and Robertico, festivals like Cuba Nostalgia, a form of media distribution on the island called el paquete, and the viral social media content of Los Pichy Boys. By unpacking this archive, Laguna explores our complex, often fraught attachments to popular culture and the way it can challenge and reify normative ideologies—especially in relation to politics and race. Transnational in his approach, Laguna argues that this at times ephemeral archive of diversión is crucial for understanding not only the diaspora, but increasingly, life on the island.