Abstract: Literary criticism is more of a field of self-realization of critics' subjectivity, which is both inseparable from the critic's subject consciousness and closely related to his continuous attempts to break through his own subject consciousness, than just the objective reflection of literary texts. This is exactly how Merezhkovsky's criticism of Chekhov works. On the aesthetic level, the critical perspectives as a writer and as a symbolist are intertwined; on the ideological level, the viewpoints of a subjective critic and of a religious explorer are constantly converting. Merezhkovsky's specific views on Chekhov's creation should be explored and at the same time attention should be paid to the specific perspectives when he makes certain comments and the possibility of diverse interpretations under the influence of the subjectivity when Merezhkovsky's "self" and "self-transcendence" compete or merge with each other. In fact, any criticism is the product of a dialogue between the critic and the writer's works from different angles, and multiple intertwined dialogues give the texts of criticism multifaceted interpretations.