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Transcultural and transnational processes have constituted some of the most crucial political, economic, social, and ideological dimensions of cultural composition in Latin America and the Caribbean since the colonial period to the present day. The manner in which these experiences have been articulated in the daily lives and imaginations of people in the region can provide insight into the formation of the respective national cultures. This paper will explore how contemporary Cuban culture has been transformed over time by national, family and interpersonal separations and absences produced by emigration and exile since 1959. Importantly, the focus will be placed on the experiences of those who remain in Cuba rather than of those who leave Cuba. Cubans in Cuba also negotiate imaginaries of displacement, dispersion, distance, and difference and, therefore, are envisioned here as integral participants in the social and cultural processes of emigration and exile. This paper will put the biographical narratives of Cubans on the island in conversation with artistic expressions from the island, to explore how – in relation to contested national histories and conflictive political discourses of exclusion that are particular to post-1959 Cuba – these emotional and psychological experiences of diaspora have penetrated the daily lives and imaginations of Cubans inside and outside Cuba and, thus, have become formative aspects of contemporary Cuban culture.