This paper analyzes the creative interaction between Ivan Bunin and Lev Shestov. After providing constructive feedback on observations and reflections from the preceding scholarly literature on the subject the author argues that the main point of convergence between the writer and the philosopher is their works on Leo Tolstoy. The study includes a textual analysis of the elements of Shestovian discourse that were discovered in Bunin’s essay The Liberation of Tolstoy. The author argues that the ending of The Liberation of (...) Tolstoy can be understood only in the context of existentialist discourse. Bunin's objections to the Shestov's view of Chekhov’s creative work have been studied in detail. In general, Bunin does not appear to be a “disciple” of Shestov, as he is engaged in a philosophical dialogue with him on equal terms. Existentialism is the closest philosophical tradition to Bunin’s thought than any others that arose in the twentieth century. (shrink)