In this chapter, Dara Goldman focuses on the case study of the “New Man” in Cuba and how it has been reconfigured in twenty-first-century LGBTQ films. The analysis focuses on Tomás Gutierrez Alea’s landmark film, Fresa y chocolate (1994), and how it positions queer sexuality vis-à-vis the revolutionary ideals and imagined future that it seeks to forge. The author also examines how recent films have repeatedly reposited and reimagined the central dialectic of Gutierrez Alea’s film, with particular attention to Mariyln Solaya’s Vestido de novia (2014). The author analyzes Fátima o el parque de la fraternidad (2015), which traces the evolution of and transgender transformation of the protagonist. The chapter places this work in dialogue with two other recent films – Conducta (2014) and Ultimos días en la Habana (2016) – that examine how masculinity is disciplined in moments of crisis. In the end, the author argues that the failures depicted in these works allow us to better understand the role of gender in Latin American cultures. As these works reimagine the parameters of gender and transgender, they confront the fundamental attachment to normative gender roles as a legitimating force in Latin American cultural traditions.