A few months before he died, Chekhov told the writer Ivan Bunin that he thought people might go on reading his writings for seven years. "Why seven?" asked Bunin. "Well, seven and a half," Chekhov replied. "That's not bad. I've got six years to live."[99]

Always modest, Chekhov could hardly have imagined the extent of his posthumous reputation. The ovations for the play The Cherry Orchard in the year of his death showed him how high he had risen in the affection of the Russian public. By then he was second in literary celebrity only to Tolstoy,[100] who outlived him by six years, but after his death, Chekhov's fame soon spread further afield. Constance Garnett's translations won him an English-language readership and the admiration of writers such as James Joyce, Virginia Woolf, and Katherine Mansfield. The issues surrounding the close similarities between Mansfield's story "The Child Who Was Tired" and Chekhov's "Sleepy" are summarised in William H. New's Reading Mansfield and Metaphors of Reform[101] The Russian critic D.S. Mirsky, who lived in England, explained Chekhov's popularity in that country by his "unusually complete rejection of what we may call the heroic values."[102] In Russia itself, Chekhov's drama fell out of fashion after the revolution, but it was later incorporated into the Soviet canon. The character Lopakhin, for example, was reinvented as a hero of the new order, taking an axe to the cherry orchard.[103][104]

One of the first non-Russians to praise Chekhov's plays was George Bernard Shaw, who subtitled his Heartbreak House "A Fantasia in the Russian Manner on English Themes," and pointed out similarities between the predicament of the British landed class and that of their Russian counterparts as depicted by Chekhov: "the same nice people, the same utter futility."[105]

In the United States, Chekhov's reputation began its rise slightly later, partly through the influence of Stanislavski's system of acting, with its notion of subtext: "Chekhov often expressed his thought not in speeches," wrote Stanislavski, "but in pauses or between the lines or in replies consisting of a single word ... the characters often feel and think things not expressed in the lines they speak."[106][107] The Group Theatre, in particular, developed the subtextual approach to drama, influencing generations of American playwrights, screenwriters, and actors, including Clifford Odets, Elia Kazan and, in particular, Lee Strasberg. In turn, Strasberg's Actors Studio and the "Method" acting approach influenced many actors, including Marlon Brando and Robert De Niro, though by then the Chekhov tradition may have been distorted by a preoccupation with realism.[108] In 1981, the playwright Tennessee Williams adapted The Seagull as The Notebook of Trigorin. One of Anton's nephews, Michael Chekhov would also contribute heavily to modern theatre, particularly through his unique acting methods which differed from Stanislavski's.

Despite Chekhov's eminence as a playwright, some writers believe that his short stories represent the greater achievement.[109] Raymond Carver, who wrote the short story "Errand" about Chekhov's death, believed that Chekhov was the greatest of all short story writers:

Chekhov's stories are as wonderful (and necessary) now as when they first appeared. It is not only the immense number of stories he wrote—for few, if any, writers have ever done more—it is the awesome frequency with which he produced masterpieces, stories that shrive us as well as delight and move us, that lay bare our emotions in ways only true art can accomplish.[110]

Ernest Hemingway, another writer influenced by Chekhov, was more grudging: "Chekhov wrote about six good stories. But he was an amateur writer."[111] And Vladimir Nabokov once complained of Chekhov's "medley of dreadful prosaisms, ready-made epithets, repetitions."[112] But he also declared "The Lady with the Dog" "one of the greatest stories ever written," despite its apparent sexism and the problematic relationship between the characters, and described Chekhov as writing "the way one person relates to another the most important things in his life, slowly and yet without a break, in a slightly subdued voice."[113]

For the writer William Boyd, Chekhov's breakthrough was to abandon what William Gerhardie called the "event plot" for something more "blurred, interrupted, mauled or otherwise tampered with by life."[114]

Virginia Woolf mused on the unique quality of a Chekhov story in The Common Reader (1925):

But is it the end, we ask? We have rather the feeling that we have overrun our signals; or it is as if a tune had stopped short without the expected chords to close it. These stories are inconclusive, we say, and proceed to frame a criticism based upon the assumption that stories ought to conclude in a way that we recognise. In so doing we raise the question of our own fitness as readers. Where the tune is familiar and the end emphatic—lovers united, villains discomfited, intrigues exposed—as it is in most Victorian fiction, we can scarcely go wrong, but where the tune is unfamiliar and the end a note of interrogation or merely the information that they went on talking, as it is in Tchekov, we need a very daring and alert sense of literature to make us hear the tune, and in particular those last notes which complete the harmony.[115]

While a Professor of Comparative Literature at Princeton University, Michael Goldman presented his view on defining the elusive quality of Chekhov's comedies stating: "Having learned that Chekhov is comic... Chekhov is comic in a very special, paradoxical way. His plays depend, as comedy does, on the vitality of the actors to make pleasurable what would otherwise be painfully awkward -- inappropriate speeches, missed connections, faux pas, stumbles, childishness -- but as part of a deeper pathos; the stumbles are not pratfalls but an energized, graceful dissolution of purpose."[116]

A character featured in Tennessee Williams' one-act play "The Lady of Lankspur Lotion" who is referred to as "The Writer" in the script, is named Anton Pavlovich Chekov.

Alan Twigg, the chief editor and publisher of BC Bookworld in Vancouver, one of Canada's leading book review magazines, wrote,

"One can argue Anton Chekhov is the second-most popular writer on the planet. Only Shakespeare outranks Chekhov in terms of movie adaptations of their work, according to the movie database IMDb. ... We generally know less about Chekhov than we know about mysterious Shakespeare."[117]

Chekhov has also influenced the work of Japanese playwrights including Shimizu Kunio, Yōji Sakate, and Ai Nagai. Chekhov and Shimizu use a mixture of light humor as well as an intense feeling of wanting something.[118] Sakate adapted several of Chekhov's plays and transformed them in the general style of .[119] Nagai also adapted Chekhov's plays, like Three Sisters, and transformed his dramatic style into Nagai's style of satirical realism while emphasizing the social issues depicted on the play.[119]

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