We examine, to the extent time permits, a trajectory of utopian literature from Plato’s Republic to the present. We read these texts through the lens of classic philosophic speculations, past and contemporary, regarding human nature, particularly, our capacity for social cooperation without coercion. Using Freud’s Civilization and Its Discontents, I articulate what I will call ‘Freud’s paradox’ with regard to the foundation and sustainability of a utopian society. Additionally, we employ Kant’s Enlightenment anthropology and philosophy of history as laying the basis for the so-called ‘blue-print’ utopias of the nineteenth century. We end with the turn to classical twentieth century dystopias and examine possible historical and philosophic reasons for the shift towards anti-utopian and dystopian writing. Throughout, it is borne in mind that the utopian novel is, first and foremost, a literary enterprise, and we ask what social functions the utopian/ dystopian novel has played and may play in the future.