The article discusses the need to reflect the challenge of uncertainty in the context of the role of art in human life. The importance of art for understanding and accepting a person himself, as well as the fateful stages of his life, is considered. A comparative analysis of the dramaturgy of A. Chekhov and B. Brecht is carried out, which reveals two opposite positions in the assessment of turning historical events (reflexive understanding and categorical condemnation) and emphasizes the importance of a reflexive assessment of what is happening and a value definition of oneself in it.