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This dissertation examines U.S.-Cuban cultural exchange around the Cuban revolutions of 1933 and 1959. It argues that the historical period from 1930-1970 represents a critical juncture in global politics, when fascination and dismay for Cuban revolutionary struggles spawned new ideas about art, aesthetics, governance, and jurisprudence as part of new state functions and cosmopolitan publics. Drawing from U.S. and Cuban sources, this project documents the ways in which cultural producers from across the political spectrum used the language of revolution to craft claims about race, class, gender, empire, and nationhood. It explains the fractured relationship following the 1959 revolution by beginning in the 1930s, when narratives of U.S.-led Pan-Americanism splintered and frayed within the broader project of neocolonialism. Cultural expressions--from folksongs and poems to presidential speeches and tourist literature--demonstrate multiple ideological positions and aesthetic forms that reveal a tension between Pan-American camaraderie on the one hand and neocolonial violence on the other. I use poetry, journalism, plays, federal policy, music, and radical literature to illustrate ideas about Cuba that spanned the ideological gamut--from socialist utopia to the tragedy of dictatorship--and their location in the generational transition from the Good Neighbor policy to Cold War containment. In the United States, these two political moments were anchored between the New Deal coalition and rise of the Old Left on the one hand, and the dawning of Kennedy/Johnson liberal internationalism and the New Left on the other. At the same time in Cuba the revolutionary culture industries restructured nationalist narratives and political ambitions based on anti-Yankee opposition, which ultimately ushered in a new Cuban state that self-fashioned itself as a leader of the Third World. I present a case study that reveals how political and cultural vectors operate in multiple directions, creating the overarching conditions that enable "minor" states to exert gravitational pull on superpowers in the production of new local tastes and sensibilities from Harlem to Havana. / text