The article deals with the studies of Chekhov's works through the early twentieth century poets' appraisal. Much attention is paid to the words of Mandelstam, Gippius, Bryusov and Tsvetaeva. In the article the question of ontological and metaphysical aspect in Chekhov's works is raised. The stories "The Steppe" and "The Black Monk" are reviewed in the framework of one plot. Perception of Chekhov's works in the Silver Age is reinterpreted. The parallels with Yesenin's poem "The Black Man" and Khlebnikov's "The Stone Woman" are drawn. The article uses historical and functional, historical and genetic as well as systematic and typological methods. The folklore commentary on Khlebnikov's and Yesenin's texts allows us to see the imagery of well-known poems in a different way and address to the plot about "the Polovets woman" which is also actualized in Chekhov's story "The Steppe". Review of Chekhov's works within a large literary and cultural context extends our vision of him as a master of the pen, a writer of not on a simple trivial level. Such literary context allows us to raise the question of metaphysical sense in Chekhov's poetics. © 2017 International Information Institute.