This dissertation proposes a possible trajectory for the configuration of male subjectivity in Latin America, from the Cuban Revolution to the consolidation of neoliberalism. Rather than a diachronic description, it is a composition of three synchronic studies of the literary and cinematic representation mechanisms of different masculinities in works by creators from Cuba, Chile and Mexico. It focuses on the connection between modernity, masculinity, nationalism and power, rejecting “the masculine” as a universal category defined by the cohesion of discourse and action, heteronormativity, and the confrontation with a spectrum of femininity. My dissertation consists of four chapters. In the first one, I present a brief history of the subject on the continent and propose a theoretical framework to discuss masculinity and consider its position in gender relations. The second chapter focuses on studying how manipulating the hero’s journey as a narrative model in Viaje a La Habana, by Reinaldo Arenas, allows for a vindication of subordinate masculinities through the rewriting of the nation's political and cultural history. I argue that the novel proposes what I call a "transvestite epic," in which the characters participate in a transvestite journey that subverts the cultural and gender paradigms on which the nation is founded. In the third chapter, I examine how through the representation of hegemonic masculinities that undergo transformations that threaten their position and undermine their dominance over the national imaginary, the novel Estrella distante by Roberto Bolaño presents an alternative narrative of an era marked by the radicality of political and artistic proposals, In the fourth and final chapter, I focus on the film Silent Light, by Carlos Reygadas. I argue that focusing on a marginal ethnic community, which speaks Low German as a daily language, is a rhetorical strategy to establish a notion of another possible community within the larger community, not to propose a claim for inclusion but to highlight some features in the larger group, the nation, by isolating them in the smaller group, the Mennonite community, through the study of personal and temporal relationships that define the subjectivity of the film's protagonist.