This dissertation is a comparative literary and cultural study that frames expressions of Cuban nationalism during the twentieth-century. The thesis analyzes representations pertaining to textual aesthetics that feature Havana as a centerpiece of Cuban-oriented cultural production. It juxtaposes the social-political interpretations found in a grouping of texts by relating the city capital to revolutionary ideology. By first focusing on the Republican era and later on the Revolution era, the thesis offers to examine how the urban realm of Havana is utilized as a mode that expresses the cultural evolution of Cuba during the last century. With the use of multinational texts within the print, film, and popular cultural genres, the dissertation argues for an evaluation of the ideological implications that arise within these cultural productions, while correlating them to an emerging global interest pertaining to things Cuban