Critically analyzing films allows for the interrogation of how such binaries as normal/abnormal, good/bad, and moral/immoral are culturally (re)inscribed, who sets the boundaries of what is deemed socially legible, and who gets to decide where these boundaries are set. This article utilizes critical discourse analysis to explore the transgender look as it relates to films with negative, conflicted, and positive readings of trans* characters. The study concludes by considering opportunities for increasing student critical analysis and thought in curricular settings and how, through critical pedagogical practices, educators can use critical pedagogy to promote equity for all marginalized populations.