The article examines the idea of the pessimistic nature of A. P. Chekhov's work, which is characteristic of both lifetime criticism of the writer and the reviews of subsequent years. The author suggests that this opinion is due, firstly, to the selection of material by critics and, secondly, to the principles of interpretation of these texts. Due to the peculiarities of journalism in the last third of the 19th century, critics did not receive all of Chekhov's works, but only selected ones, mainly short stories and novellas published in "Russkaja mysl" in the 1890s. They received a wide response, quickly became famous, remembered, and subsequently were considered milestones in the writer's work. These difficult texts were usually read as not having a positive beginning - Chekhov's contemporaries traditionally paid special attention to this category. The idea that Chekhov was a pessimist was formed gradually and consistently. In the late 1880s and mid - 1890s, critics noted a specific feature in Chekhov's prose and drama, which they considered a manifestation of pessimism: the writer rarely indicates the possibility of changes for the better and puts the characters in a hopeless position. Since the late 1890s, the concept of Chekhov's pessimism has expanded and been supplemented: pessimism has also been understood as an emotion - a sad, sad mood, a special atmosphere. Subsequently, these two points of view existed simultaneously: the definition of "pessimism" did not have a single meaning.