Uncle Vanya was first published in 1897 but was not performed by the Moscow Art Theater, where it premiered, until October 26,1899. Well received by audiences, Uncle Vanya was not entirely a success in Chekhov's own estimation. The directors at the Moscow Art Theater—Konstantin Stanislavsky and V. I. Nemirovich-Danchenko—did not understand Chekhov's artistic vision, and Chekhov, sick with tuberculosis by the time Uncle Vanya was produced, could not intervene. Nemirovich-Danchenko wrote, ‘‘Chekhov was incapable of advising actors. ... Everything appeared so comprehensible to him: 'Why, I have written it all down,' he would answer.’’ Stanislavsky admitted to being slightly confounded by Chekhov's plays; he said that when he went to produce The Sea Gull, he didn't know how to proceed, the words were too simple.

Even if Stanislavsky and Nemirovich-Danchenko failed to fully appreciate Chekhov's vision, Uncle Vanya was much better received than its earlier incarnation, The Wood Demon. Chekhov's second full-length play, The Wood Demon was rejected by two theaters before premiering in Moscow in December 1889; it played for only three performances before closing. Chekhov insisted that The Wood Demon never be staged again, and he would not permit it to be included in his Collected Works.

Although Chekhov quickly gained fame for his short stories, his plays puzzled many Russian audiences and even other Russian writers. When Chekhov met Leo Tolstoy the War and Peace author said to him: ‘‘But I still can't stand your plays. Shakespeare's are terrible, but yours are even worse!’’ Tolstoy was harsh in his critique of Uncle Vanya, which he saw performed by the Moscow Art Theater on January 24, 1900. The novelist berated Chekhov for having done nothing to support Astrov's contention that he and Vanya are the only decent and intelligent men in the district. Why, asked Tolstoy, should the audience have such a high opinion of these two men? Pitcher quoted Tolstoy as having said that Vanya and Astrov ‘‘had always been bad and mediocre, and that is why their sufferings cannot be worthy of interest.''

However, some critics point out that Tolstoy's public statements may not have been entirely accurate. Pitcher noted that Tolstoy sketched out the plan for his own play, The Living Corpse, after having seen Uncle Vanya. As Pitcher stated: ' 'Although Tolstoy, the rational thinker, could not help finding Chekhov's play inadequate, Tolstoy, the man of feeling, seems to have responded more positively to Uncle Vanya than he was willing to admit.’’

Thomas A. Eekman, in his introduction to Critical Essays on Anton Chekhov, said that Chekhov was not a darling of early critics, including the traditional Russian populists. Eekman cited Nikolai K. Mikhailovsky, who blamed Chekhov for writing without social concern and for failing to adequately portray the peasants. Socialists, noted Eekman, thought Chekhov lacked political and revolutionary spirit. Vladimir Nabokov in Critical Essays on Anton Chekhov, commented on this exact point: ' 'What rather irritated his politically minded critics was that nowhere does the author assign this type to any definite party or give him any definite political program. But that is the whole point. Chekhov's inefficient idealists were neither terrorists, nor Social Democrats, nor budding Bolsheviks, nor any of the numberless members of numberless revolutionary parties in Russia.’’

Those critics who have not viewed Chekhov through a political lens have proven more generous. One prevailing opinion is that Chekhov gave expression to the loss and hopelessness of the Russian intelligentsia and landowners in the years leading up to the Russian Revolution. In the Soviet Union after the Revolution, a country radically different from old Russia, critics tended to dismiss Chekhov as a representative of bygone times.

Nabokov hailed Chekhov as a true artist, but he found that his artistry did not lie in his word choice. Wrote Nabokov: ‘‘Russian critics have noted that Chekhov's style, his choice of words and so on, did not reveal any of those special artistic preoccupations that obsessed, for instance, Gogol or Flaubert or Henry James. His dictionary is poor ... his literary style goes to parties clad in its everyday suit. .. . The magical part of it is that in spite of his tolerating flaws which a bright beginner would have avoided ... Chekhov managed to convey an impression of artistic beauty far surpassing that of many writers who thought they knew what rich beautiful prose was.... The variety of his moods, the flicker of his charming wit, the deeply artistic economy of characterization, the vivid detail, and the fade-out of human life—all the peculiar Chekhovian features—are enhanced by being suffused and surrounded by a faintly iridescent verbal haziness.’’

Chekhov has always been highly regarded in Great Britain and the United States. In Great Britain in the 1920s, writers like Virginia Woolf and John Galsworthy embraced him, and Chekhov is revered in the United States today; his plays are frequently revived in both countries. Some critics have noted that this is odd, since Chekhov's plays—with their overriding sense of helplessness and their plotlessness—are not what usually constitutes a theatrical success. Eric Bentley wrote in Critical Essays on Anton Chekhov: ' 'Why is it that scarcely a year passes without a major Broadway or West end production of a Chekhov play? Chekhov's plays—at least by reputation, which in commercial theater is the important thing—are plotless, monotonous, drab, and intellectual: find the opposite of these four adjectives and you have a recipe for a smash hit.’’ Performing Chekhov, Bentley suggested, is an act of rebellion against the system: ‘‘It is as if the theater remembers Chekhov when it remembers its conscience.’’