This chapter attempts to decipher Marcuse’s political understanding of freedom by focusing on his psychoanalytic and aesthetic thought. Although one may consider psychoanalysis and aesthetics as the privileged provinces of individual freedom, Marcuse’s social-historical perspective did not allow a de-politicization of the concept of freedom, a trend that in our days appears as pervasive as ever. It is argued that Marcuse’s aversion to “esoteric” or particularistic solutions to modern forms of oppression co-exists, not always unproblematically, with a philosophical appreciation of the anthropological basis of psychical and artistic expression. In psychoanalysis, a non-repressive renunciation may be a contradiction in terms, while in aesthetics, art struggles to establish its critical authority through its estrangement from externality. Or because of that, Marcuse argued. In exploring this tension between the ontological and the political substantiation of freedom in art and psychoanalysis, Marcuse followed, at his merit, a praxeological course that was often at odds with its macro-sociological assumptions. The immanence of this problem was already apparent in Rousseau’s universalist anthropology, where the examination of the social foundations of freedom was at its early stages.