This article examines how Sean O’Casey’s Juno and the Paycock, written in 1924, anticipated the postmodern conception of gender, or more accurately, the postmodern deconstruction of gender as merely repetitive patterns of behavior. The focus is on how the play dramatizes the Foucauldian notion of the death of man in the neurotic and irresponsible behavior of the male characters. Taking the psychological vertical approach in the analysis, the article adds to the scholarly work that has been written about the play, which mostly focused on its sociopolitical and religious aspects. The analysis this article sets forth shows how O’Casey’s representation (or perhaps mal-representation) of male characters was symptomatic of the cultural upsurge that later came to be known as postmodernism. In so doing, the article makes a curious link between O’Casey’s representation of neurotic men and the more recent inception of postmodernism and its deconstruction of gender. This link, in other words, is between neurosis and deconstruction, between psychological disturbances and the much-celebrated postmodern theory that came later. Thus, the article concludes with the peculiar question of how much of postmodern thought was, albeit unconsciously, predicated upon psychological degeneration, especially when it comes to its deconstruction of gender dynamics.