This article examines the role of insomnia in Emil Cioran’s philosophy. Taken as a whole, his work appears to be exceptionally significant both from the point of view of anthropology and illness narrative studies. There has never been any doubt that his life and work are dominated by a sense of ennui, loneliness and estrangement. Yet these themes are merely symptoms of more fundamental problems he grappled with, i.e. the grotesque nature everyday life, ecstasy in a life without gods, being an absolute-in-itself and absolute-for itself, etc. This study is focused on insomnia, treated as a primary anthropological category and studied with the help of phenomenological and hermen-eutical methodology. Drawing on, among others, the philosophy of Martin Heidegger and Arthur Schopenhauer, the article formulates a set of substantially new conceptual propositions that offer a new approach to the problematics of Cioran’s work.