This article discusses Stepun’s philosophical and sociological approaches to Russian history and culture. The subject of the analysis is the historical and artistic image of Russia created by Stepun in philosophical journalism and memoirs. A special place is given to the revealing of the foundations of Stepun’s philosophy of culture, as well as to develop specific ways of analyzing the cultural history of Russia by synthesizing philosophical reflection with the method of sociological observation. The article shows how Stepun retains a logical framework and a philosophical lexicon of the neo-Kantianism theory of culture in his sociological descriptions of the post-revolutionary history of Russia. Stepun takes the position of “participant observation” and enriches the interpretation of events using the methods of sociological analysis. This essay also discusses the way in which Stepun comprehended the idea of Russia in his social-philosophical analysis of Bolshevism. This paper explicates Stepun’s main historical and philosophical thesis that there has been a degeneration of political ideas into ideology and ideocracy in Bolshevism. Special attention is given to how Stepun contrasts the humanistic values of culture against the political ideologies of the twentieth century, which denies both freedom and the Christian faith. The article traces his philosophical solution to the problem of the Russian Revolution. His philosophical idea of Russian culture is considered as a form of the existence of a creative person possessing freedom and as a religious experience, and became a moral credo of Stepun.