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Chekhov had at first written stories only for the money, but as his artistic ambition grew, he made formal innovations which have influenced the evolution of the modern short story. His originality consists in an early use of the stream-of-consciousness technique, later adopted by James Joyce and other modernists, combined with a disavowal of the moral finality of traditional story structure. He made no apologies for the difficulties this posed to readers, insisting that the role of an artist was to ask questions, not to answer them

Anton Chekhov was born on 29 January 1860, the third of six surviving children, in Taganrog, a port on the Sea of Azov in southern Russia where his father, Pavel Yegorovich Chekhov, the son of a former serf, ran a grocery store. A director of the parish choir, devout Orthodox Christian, and physically abusive father, Pavel Chekhov has been seen by some historians as the model for his son's many portraits of hypocrisy. Chekhov's mother, Yevgeniya, was an excellent storyteller who entertained the children with tales of her travels with her cloth-merchant father all over Russia. "Our talents we got from our father", Chekhov remembered, "but our soul from our mother."

In adulthood, Chekhov was to criticise his brother Alexander's treatment of his wife and children by reminding him of Pavel’s tyranny:

Let me ask you to recall that it was despotism and lying that ruined your mother's youth. Despotism and lying so mutilated our childhood that it's sickening and frightening to think about it. Remember the horror and disgust we felt in those times when Father threw a tantrum at dinner over too much salt in the soup and called Mother a fool.

Chekhov attended a school for Greek boys, followed by the Taganrog gymnasium, now renamed the Chekhov Gymnasium, where he was kept down for a year at fifteen for failing a Greek exam.He sang at the Greek Orthodox monastery in Taganrog and in his father's choirs. In a letter of 1892, he used the word "suffering" to describe his childhood and recalled:

When my brothers and I used to stand in the middle of the church and sing the trio "May my prayer be exalted", or "The Archangel's Voice", everyone looked at us with emotion and envied our parents, but we at that moment felt like little convicts.

In 1876, Chekhov's father was declared bankrupt after over-extending his finances building a new house, and to avoid the debtor's prison fled to Moscow, where his two eldest sons, Alexander and Nikolai, were attending university. The family lived in poverty in Moscow, Chekhov's mother physically and emotionally broken. Chekhov was left behind to sell the family possessions and finish his education.

Chekhov remained in Taganrog for three more years, boarding with a man called Selivanov who, like Lopakhin in The Cherry Orchard, had bailed out the family for the price of their house. Chekhov had to pay for his own education, which he managed by—among other jobs—private tutoring, catching and selling goldfinches, and selling short sketches to the newspapers. He sent every ruble he could spare to Moscow, along with humorous letters to cheer up the family.During this time he read widely and analytically, including Cervantes, Turgenev, Goncharov, and Schopenhauer;and he wrote a full-length comedy drama, Fatherless, which his brother Alexander dismissed as "an inexcusable though innocent fabrication."Chekhov also enjoyed a series of love affairs, one with the wife of a teacher.

In 1879, Chekhov completed his schooling and joined his family in Moscow, having gained admission to the medical school at Moscow University.

Chekhov now assumed responsibility for the whole family. To support them and to pay his tuition fees, he daily wrote short, humorous sketches and vignettes of contemporary Russian life, many under pseudonyms such as "Antosha Chekhonte" (Антоша Чехонте) and "Man without a Spleen" (Человек без селезенки). His prodigious output gradually earned him a reputation as a satirical chronicler of Russian street life, and by 1882 he was writing for Oskolki (Fragments), owned by Nikolai Leikin, one of the leading publishers of the time. Chekhov's tone at this stage was harsher than that familiar from his mature fiction.

In 1884, Chekhov qualified as a physician, which he considered his principal profession though he made little money from it and treated the poor for free. In 1884 and 1885, Chekhov found himself coughing blood, and in 1886 the attacks worsened; but he would not admit tuberculosis to his family and friends, confessing to Leikin, "I am afraid to submit myself to be sounded by my colleagues." He continued writing for weekly periodicals, earning enough money to move the family into progressively better accommodation. Early in 1886 he was invited to write for one of the most popular papers in St. Petersburg, Novoye Vremya (New Times), owned and edited by the millionaire magnate Alexey Suvorin, who paid per line a rate double Leikin's and allowed him three times the space.Suvorin was to become a lifelong friend, perhaps Chekhov's closest.

Before long, Chekhov was attracting literary as well as popular attention. The sixty-four-year-old Dmitry Grigorovich, a celebrated Russian writer of the day, wrote to Chekhov after reading his short story The Huntsman, "You have real talent—a talent which places you in the front rank among writers in the new generation." He went on to advise Chekhov to slow down, write less, and concentrate on literary quality.

Chekhov replied that the letter had struck him "like a thunderbolt" and confessed, "I have written my stories the way reporters write up their notes about fires—mechanically, half-consciously, caring nothing about either the reader or myself." The admission may have done Chekhov a disservice, since early manuscripts reveal that he often wrote with extreme care, continually revising. Grigorovich's advice nevertheless inspired a more serious, artistic ambition in the twenty-six-year-old. In 1887, with a little string-pulling by Grigorovich, the short story collection At Dusk (V Sumerkakh) won Chekhov the coveted Pushkin Prize "for the best literary production distinguished by high artistic worth."

That year, exhausted from overwork and ill health, Chekhov took a trip to Ukraine which reawakened him to the beauty of the steppe. On his return, he began the novella-length short story The Steppe, "something rather odd and much too original," eventually published in Severny Vestnik (The Northern Herald). In a narrative which drifts with the thought processes of the characters, Chekhov evokes a chaise journey across the steppe through the eyes of a young boy sent to live away from home, his companions a priest and a merchant. The Steppe, which has been called a "dictionary of Chekhov's poetics", represented a significant advance for Chekhov, exhibiting much of the quality of his mature fiction and winning him publication in a literary journal rather than a newspaper.

In autumn 1887, a theater manager named Korsh commissioned Chekhov to write a play, the result being Ivanov, written in a fortnight and produced that November. Though Chekhov found the experience "sickening", and painted a comic portrait of the chaotic production in a letter to his brother Alexander, the play was a hit and was praised, to Chekhov's bemusement, as a work of originality. Mikhail Chekhov considered Ivanov a key moment in his brother's intellectual development and literary career. From this period comes an observation of Chekhov's which has become known as "Chekhov's gun", noted by Ilia Gurliand from a conversation: "If in Act I you have a pistol hanging on the wall, then it must fire in the last act."

The death of Chekhov's brother Nikolai from tuberculosis in 1889 influenced A Dreary Story, finished that September, about a man who confronts the end of a life which he realizes has been without purpose. Mikhail Chekhov, who recorded his brother's depression and restlessness after Nikolai's death, was researching prisons at the time as part of his law studies, and Anton Chekhov, in a search for purpose in his own life, himself soon became obsessed with the issue of prison reform

In 1890, Chekhov undertook an arduous journey by train, horse-drawn carriage, and river steamer to the far east of Russia and the katorga, or penal colony, on Sakhalin Island, north of Japan, where he spent three months interviewing thousands of convicts and settlers for a census. The letters Chekhov wrote during the two-and-a-half month journey to Sakhalin are considered among his best.His remarks to his sister about Tomsk were to become notorious.

"Tomsk is a very dull town. To judge from the drunkards whose acquaintance I have made, and from the intellectual people who have come to the hotel to pay their respects to me, the inhabitants are very dull too."

The inhabitants of Tomsk later retaliated by erecting a mocking statue of Chekhov.

What Chekhov witnessed on Sakhalin shocked and angered him, including floggings, embezzlement of supplies, and forced prostitution of women: "There were times", he wrote, when "I felt that I saw before me the extreme limits of man's degradation." He was particularly moved by the plight of the children living in the penal colony with their parents. For example:

On the Amur steamer going to Sakhalin, there was a convict with fetters on his legs who had murdered his wife. His daughter, a little girl of six, was with him. I noticed wherever the convict moved the little girl scrambled after him, holding on to his fetters. At night the child slept with the convicts and soldiers all in a heap together.

Chekhov later concluded that charity and subscription were not the answer, but that the government had a duty to finance humane treatment of the convicts. His findings were published in 1893 and 1894 as Ostrov Sakhalin (The Island of Sakhalin), a work of social science - not literature - worthy and informative rather than brilliant. Chekhov found literary expression for the hell of Sakhalin in his long short story The Murder, the last section of which is set on Sakhalin, where the murderer Yakov loads coal in the night, longing for home.

In 1892, Chekhov bought the small country estate of Melikhovo, about forty miles south of Moscow, where he lived until 1899 with his family. "It's nice to be a lord", he joked to Shcheglov; but he took his responsibilities as a landlord seriously and soon made himself useful to the local peasants. As well as organising relief for victims of the famine and cholera outbreaks of 1892, he went on to build three schools, a fire station, and a clinic, and to donate his medical services to peasants for miles around, despite frequent recurrences of his tuberculosis.

Mikhail Chekhov, a member of the household at Melikhovo, described the extent of his brother's medical commitments:

From the first day that Chekhov moved to Melikhovo the sick began flocking to him from twenty miles around. They came on foot or were brought in carts, and often he was fetched to patients at a distance. Sometimes from early in the morning peasant women and children were standing before his door waiting.

Mikhail Chekhov, a member of the household at Melikhovo, described the extent of his brother's medical commitments:

From the first day that Chekhov moved to Melikhovo the sick began flocking to him from twenty miles around. They came on foot or were brought in carts, and often he was fetched to patients at a distance. Sometimes from early in the morning peasant women and children were standing before his door waiting.

Chekhov’s expenditure on drugs was considerable; but the greatest cost was making journeys of several hours to visit the sick, which reduced his time for writing. Chekhov’s work as a doctor, however, enriched his writing by bringing him into intimate contact with all sections of Russian society: for example, he witnessed at first hand the peasants' unhealthy and cramped living conditions, which he recalled in his short story Peasants. Chekhov visited the upper classes as well, recording in his notebook: "Aristocrats? The same ugly bodies and physical uncleanliness, the same toothless old age and disgusting death, as with market-women."

Chekhov began writing his play The Seagull in 1894, in a lodge he had built in the orchard at Melikhovo. In the two years since moving to the estate, he had refurbished the house, taken up agriculture and horticulture, tended orchard and pond, and planted many trees, which, according to Mikhail, he "looked after… as though they were his children. Like Colonel Vershinin in his Three Sisters, as he looked at them he dreamed of what they would be like in three or four hundred years."

The first night of The Seagull on 17 October 1896 at the Alexandrinsky Theatre in Petersburg was a fiasco, booed by the audience, and the play's reception stung Chekhov into renouncing the theatre. But the play so impressed the theatre director Vladimir Nemirovich-Danchenko that he convinced his colleague Constantin Stanislavski to direct it for the innovative Moscow Art Theatre in 1898. Stanislavski's attention to psychological realism and ensemble playing coaxed the buried subtleties from the text and restored Chekhov's interest in playwriting. The Art Theatre commissioned more plays from Chekhov and the following year staged Uncle Vanya, which Chekhov had completed in 1896.

In March 1897 Chekhov suffered a major hemorrhage of the lungs while on a visit to Moscow and, with great difficulty, was persuaded to enter a clinic, where the doctors diagnosed tuberculosis on the upper part of his lungs and ordered a change in his manner of life.

After his father's death in 1898, Chekhov bought a plot of land on the outskirts of Yalta and built a villa there, into which he moved with his mother and sister the following year. Though he planted trees and flowers in Yalta, kept dogs and tame cranes, and received guests such as Leo Tolstoy and Maxim Gorky, Chekhov was always relieved to leave his "hot Siberia" for Moscow or travels abroad. He vowed to move to Taganrog as soon as a water supply was installed there. In Yalta he completed two more plays for the Art Theatre, composing with greater difficulty than in the days when he "wrote serenely, the way I eat pancakes now"; he took a year each over Three Sisters and The Cherry Orchard.

On 25 May 1901 Chekhov married Olga Knipper—quietly, owing to his horror of weddings—a former protegée and sometime lover of Nemirovich-Danchenko whom he had first met at rehearsals for The Seagull. Up to that point, Chekhov, called "Russia's most elusive literary bachelor", had preferred passing liaisons and visits to brothels over commitment; he had once written to Suvorin:

By all means I will be married if you wish it. But on these conditions: everything must be as it has been hitherto—that is, she must live in Moscow while I live in the country, and I will come and see her… give me a wife who, like the moon, won't appear in my sky every day.

The letter proved prophetic of Chekhov's marital arrangements with Olga: he lived largely at Yalta, she in Moscow, pursuing her acting career. In 1902, Olga suffered a miscarriage; and Donald Rayfield has offered evidence, based on the couple's letters, that conception may have occurred when Chekhov and Olga were apart, although Russian scholars have conclusively refuted that claim. The literary legacy of this long-distance marriage is a correspondence which preserves gems of theatre history, including shared complaints about Stanislavski's directing methods and Chekhov's advice to Olga about performing in his plays.

In Yalta, Chekhov wrote one of his most famous stories, The Lady with the Dog (also called Lady with Lapdog), which depicts what at first seems a casual liaison between a married man and a married woman in Yalta. Neither expects anything lasting from the encounter, but they find themselves drawn back to each other, risking the security of their family lives.

By May 1904, Chekhov was terminally ill with tuberculosis. "Everyone who saw him secretly thought the end was not far off", Mikhail Chekhov recalled, "but the nearer Chekhov was to the end, the less he seemed to realize it." On 3 June he set off with Olga for the German spa town of Badenweiler in the Black Forest, from where he wrote outwardly jovial letters to his sister Masha describing the food and surroundings and assuring her and his mother that he was getting better. In his last letter, he complained about the way the German women dressed.

Chekhov’s death has become one of "the great set pieces of literary history", retold, embroidered, and fictionalised many times since, notably in the short story Errand by Raymond Carver. In 1908, Olga wrote this account of her husband’s last moments:

Anton sat up unusually straight and said loudly and clearly (although he knew almost no German): Ich sterbe ("I'm dying"). The doctor calmed him, took a syringe, gave him an injection of camphor, and ordered champagne. Anton took a full glass, examined it, smiled at me and said: "It's a long time since I drank champagne." He drained it, lay quietly on his left side, and I just had time to run to him and lean across the bed and call to him, but he had stopped breathing and was sleeping peacefully as a child...

Chekhov’s body was transported to Moscow in a refrigerated railway car for fresh oysters, a detail which offended Gorky.Some of the thousands of mourners followed the funeral procession of a General Keller by mistake, to the accompaniment of a military band. Chekhov was buried next to his father at the Novodevichy Cemetery.

A few months before he died, Chekhov told the writer Ivan Bunin he thought people might go on reading him 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."

Always modest, Chekhov could hardly have imagined the extent of his posthumous reputation. The ovations for 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, 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 1910 story The Child Who Was Tired and Chekhov's Sleepy are summarised in William H. New's Reading Mansfield and Metaphors of Reform] 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."[86] In Russia itself, Chekhov's drama fell out of fashion after the revolution but was later adapted to the Soviet agenda, with the character Lopakhin, for example, reinvented as a hero of the new order, taking an axe to the cherry orchard.

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 noted 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."

In America, 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." 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. In 1981, the playwright Tennessee Williams adapted The Seagull as The Notebook of Trigorin.

Despite Chekhov's eminence as a playwright, some writers believe his short stories represent the greater achievement. Raymond Carver, who wrote the short story Errand about Chekhov's death, believed Chekhov 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

Ernest Hemingway another writer influenced by Chekhov, was more grudging: "Chekhov wrote about 6 good stories. But he was an amateur writer." And Vladimir Nabokov once complained of Chekhov's "medley of dreadful prosaisms, ready-made epithets, repetitions." But he also declared The Lady with the Dog "one of the greatest stories ever written" 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."

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."

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.