The article deals with the critical and philosophical interpretations of Chekhov’s narrative style through the prism of crisis trends in art from the end of the 19th to the first third of the 20th century. Evaluating Chekhov’s style from various perspectives provides a comprehensive picture of Russian intellectual life in the first third of the 20th century. Lev Shestov proposes distinction between two eras in Russian literature (Turgenev’s and Chekhov’s) and demonstrates the fundamental difference between the two styles of thought and narrative. These ideas became clichés in criticism in the 1920s and 1930s. It is important to note that the same characteristics of Chekhov’s style (fragmentation of experience, predominance of detail over the whole) received different interpretations. Thus, V. Shklovsky considered the style of Chekhov’s early stories to be the most perfect. M. Gershenzon demonstrated how the predominance of detail in Chekhov’s narrative distorts the “truth of life.” K. Motchoulski and W. Weidlé observed in Chekhov’s artistic style symptoms of a “crisis of imagination” and the “declining of art.”