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This article investigates artistic representations during U.S. military occupations in Nicaragua, Haiti, and the Dominican Republic from 1912 to 1934, with an emphasis on song and literature. It asks how occupied nations’ cultural products most effectively represented attitudes toward occupation. It finds two separate models: an uncompromising, popular one in Nicaragua, regional in origin yet largely produced by transnational insurrectionists involved in violently resisting intervention and using culture as a political tool; and a much more ambivalent one in Haiti and the Dominican Republic, produced mostly by national yet insular and traditional elites using culture as an expression of not only moral opprobrium toward occupation forces but also significant self-criticism. It portrays both models as reflecting fundamentally different poles of resistance and thus suggesting how social differences undergirded the divisions in the Latin American response to U.S. empire.