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Representations and the political imagination of Guantánamo, Cuba are divided. Serene mountain regions line the eastern coast of Guantánamo province, horse carts clicking along the roads, carrying families and workers to their destinations. Rural artists perform in open-air plazas and in fields. Guantánamo City bustles with cars, storefronts, and children running to school in red uniforms. Its urban artists perform in traditional theatres with proscenium stages. The U.S. Naval base looms in the distance: it carries the same name, but is seemingly a world away from the everyday. The base is a ubiquitous yet often forgotten presence in the province itself, unseen from most areas outside of the closest towns, Caimanera or Boquerón. It is mythologized more often than physically experienced. For many Cubans, it symbolizes imperialism and antagonism, but to others, freedom and escape, although it is an extremely dangerous route to freedom. This paper examines relationships of inside-outside, us-them, and the past-future of what both Guantanamo the homeland and Guantanamo the base mean to Cubans. Perspectives are analyzed primarily through discourses of the artistic and performed – through narrative visions and imaginings of Cuba’s culture-keepers. Where is “Guantanamo” and how is its turbulent image being transformed in cultural memory?