This dissertation focuses on key ideological and aesthetic debates that arose in the mid-1960s in response to and within the Cuban Revolution. In the 20th century, revolutionary struggle and national liberation lie at the core of ideological confrontations between (neo)colonies and traditional imperial powers, and in the Western Hemisphere Cuba was at the vortex of a war of ideas that was being waged between the United States and the Soviet Union on the one hand, and between traditional imperial powers and revolutionary or independence movements on the other. In these conflicts the cultural sphere became an intensely contested terrain. In the first of four chapters, I attempt to demonstrate the liberal, anti-Communist orientation of the Latin American literary journal Mundo Nuevo, by analyzing the content of four articles on the Vietnam War that were included in the second issue (August 1966). In the controversy surrounding the indirect CIA support for Mundo Nuevo, Cuban and Latin American critics of the journal have referred to the four texts as an ideological concession by the editor, Emir Rodríguez Monegal, while supporters point to the articles as an example of the journal's willingness to critique the policies of Washington from a position of Cold War neutrality. I argue that neither position is accurate because the criticism of the war that was articulated in three of these four texts reflects an assimilation of the ideological narrative promoted by the Congress for Cultural Freedom since its foundation in 1950. In the second chapter, I review a debate on the novel of the Cuban Revolution between Cuban literary critics José Antonio Portuondo and Ambrosio Fornet that was published in La Gaceta de Cuba in 1964 and 1965. The older Portuondo defends a relatively provincial position against the more cosmopolitan perspective of the younger Fornet. While both of these Cuban critics defended the Revolution against counterrevolutionary cultural projects such as Mundo Nuevo, the literary aesthetic defended by Fornet overlaps partially with Emir Rodríguez Monegal's promotion of Modernist and avant-garde literary tendencies. The third chapter, which is an analysis of the second novel published by Santiago writer José Soler Puig: En el año de enero (1963), attempts to highlight a kind of silent debate within the cultural sphere of the Cuban Revolution. I hypothesize that due to the inclusion of very critical voices in this novel, which reflects the societal tensions brought about by the socioeconomic policies implemented by Fidel Castro in 1959, the author was marginalized by the new cultural institutions. In the fourth chapter, I review two important debates from 1966 in which a young, militant Jesús Díaz rejects—as degenerate, impoverished or counterrevolutionary cultural manifestations—not only the incipient, subaltern literary movement of El Puente, represented in the debate by Ana María Simo, but also the populist, folkloric poetry of Jesús Orta Ruiz.