This essay is based on a comparative analysis of The Cherry Orchard by Chekhov and A Streetcar named Desire by Tennessee Williams. The main objective of this essay is to give a complex analysis of these pieces revealing similar forms and ideas, recurrent motifs, symbols, theatrical devises used by both playwrights, and show their place in the aesthetic systems of both artists, and in the world picture they draw in their dramas. Unlike many other modem interpreters of classics who often use well known plots to express totally different if not the opposite meaning, Williams remaining an original and imaginative playwright follows the path laid by Chekhov, developing in his works a similar poetic style, widening and enriching the scale of expressive devices, which is shown on the basis of comparative analysis. And the major affinity is not even in the likeness of particular plots, characters or artistic means but in the fact that both artists tend to depict concrete situations in a broad historical and philosophic perspective. Therefore, their plays acquire a symbolic meaning, becoming emblems of the time, epoch and human life as such. This, as I try to show, is the major thing Williams learnt from Chekhov.