The aim of the paper is to analyse the theoretical base of tragic culture in the writings of F. Nietzsche and V. I. Ivanov. The result of the proposed analysis is the comparison of similarities and differences concerning the cultural role of tragedy in the philosophy of mentioned authors. The philosophers — Nietzsche, the implacable enemy of the historical Christianity and Ivanov, the Christian philosopher of culture, philologist and translator — both postulate creating and preserving tragic culture. According to both authors, the main task of culture is to confront the human being with the most terrible aspects of life. This ruthless requirement allows us to claim that perverse heroism is a general mood and the most important imperative of Nietzsche’s and Ivanov’s philosophy of culture. The imperative to preserve the tragic principle in culture is in fact an imperative to become a superhuman. The starting point of the analysis is the theorem of Nietzsche who defines a tragic worldview as the opposite of a theoretical one. The essence of the theoretical approach is an overlooking of the tragic dimension of life, which allows man to establish a coherent, justified and safe picture of the world. The tragic approach, emphasizing the inevitability of suffering and the lack of metaphysical foundation, opposes the optimism of the theoretical one. Ivanov, as Nietzsche, was fascinated with Dionysian idea but he interpreted it quite differently. The Russian author accepted Dionysus not as the opposite, but as a prefiguration of Christ. Thus, he drew attention to the presence of the tragic moment in Christianity. The height of Ivanov’s dispute with Nietzsche is a completely different interpretation of the idea of superhuman, which presents a totally different understanding of self-transgression and vastly different value systems.