This paper aims to interrogate Freirean critical pedagogy via the work of Jacques Lacan in order to shed new light on psychoanalytic issues that arise when engaging in critical pedagogical work. First, through a close reading of Freire's "Pedagogy of the Oppressed," the author delineates Freire's conception of the human subject, the mechanisms that function to oppress subjects and prevent full humanization, and the process by which subjects can begin to imagine new possibilities outside of the oppressor/oppressed relationship. Next, careful consideration is given to Lacan's formulation of the function of the imaginary in the emergence of the subject, which was most clearly articulated in his seminal work "The Mirror Stage as Formative of the Function of the I as Revealed in Psychoanalytic Experience." This engagement with these two thinkers emphasizes what Lacan can teach us about the complex relationship between identity construction, subjectivity, and the role of intersubjective relations in theorizing and creating a more just world.