This paper posits that an infusion of psychoanalytic concepts into the teaching of sociology in undergraduate liberal arts curricula offers a route to expanding students’ understanding of how self and society are entwined in a condition of mutual crisis in contemporary society. We argue that the liberatory project at the core of the liberal arts is served well by linking the critical perspectives found in these two disciplines. We provide as specific examples from our own teaching: (1) a demonstration of how Freud’s concept of neurosis has an affinity with Marx’s concept of alienation; and (2) a discussion of how the torture sequence in Orwell’s 1984 presents an inversion of a psychoanalytic treatment through which the power of propaganda is illuminated. We conclude that teaching the two disciplines in tandem helps students grasp how the self is a socially constructed entity and how the orthodoxies of neurosis and social control are available for critique and change.