Anton Pavlevich Chekhov was born on January 17th, 1860, in Taganrog, Russia. His father Pavel was a shopkeeper the town, which was small, provincial, and on the Sea of Azov in the south of Russia, and his grandfather was Egor Chekhov, a serf. Serfs were the legal property of the landowners who owned the property on which they resided; it was thus a form of slavery. In 1841, Egor bought freedom for himself and his family at the price of 875 rubles.

Russia had been changing ever since the early 18th century, when Tsar Peter the Great carried out a series of reforms with the intent of modernizing Russia in Western Europe's image. European styles in fashion and art were imported, the Western canon was widely read among the nobility, and French was adopted as the language of cultured discourse. A large government bureaucracy was created; the achievement of rank became an obsession of Russian life. During Chekhov's childhood, in the time of Tsar Alexander II, a second wave of reforms was underway, reforms that further liberalized the country and its economy. The most important of these was the Emancipation Declaration of 1861, which freed the serfs from bondage. These reforms caused great controversy, as they introduced what was, in effect, the beginning of a free-market economy, undermining the power of the nobility, and sometimes even impoverishing them. The situation displayed in The Cherry Orchard, of a wealthy landowning family forced to sell their estate in order to pay their debts, was thus a familiar one in the Russian society of Chekhov's day.

Chekhov himself had a relatively quiet childhood. He attended the local Russian grammar school, worked in his father's store and occasionally wrote small pieces for the amusement of his family. Taganrog was not a typical provincial town; it was a multicultural port, with Italians, Greeks, and Turks residing in the wealthier sections of town and Russians such as the Chekhovs living in comparatively poor suburbs. It had a theater, which the young Chekhov would often visit. When Chekhov was sixteen, Pavel's store failed, and the entire family had to move to Moscow—the entire family, that is, except for Anton. A merchant (and friend of the family) had helped the Chekhovs with a loan, but insisted on keeping Anton with him in the house as a kind of collateral. As soon as he could, he left Taganrog in order to pursue medical studies in Moscow in 1879 at the age of 19.

That year, Chekhov began to write comic stories in order to pay his medical school tuition. By the time he was twenty, he was employed by The Spectator magazine as their regular humorist. Over ninety percent of Chekhov's published work appeared in magazines before he was twenty-eight, and, by this age, he had already established himself as a premier writer of short stories. As he developed as a writer, his stories began to take on deeper and more profound themes, as he moved away from his comic roots.

To this day, Chekhov's literary reputation primarily rests with his short stories, and Chekhov's early plays, written primarily in his early 20s, are not well-remembered. It was only in 1896 that he began to turn his attention back to drama; in the eight remaining years before his death, he managed to complete four plays: The Seagull, Uncle Vanya, The Three Sisters, and The Cherry Orchard.

The first performance of The Seagull was nearly laughed off the stage; it was criticized as dull, unimaginative, and lacking any sort of dramatic tension (a critical undercurrent that has survived in Russia to this day). Only gradually did Chekhov's new form of drama, emphasizing characterization, detail and symbolism instead of plot development and incident, gain acceptance. Chekhov was the in-house playwright for the Moscow Arts Theatre, which had been founded by his friend Vladimir Nemirovich-Davchenko. During this time, he fell in love with one of the Theatre's leading actresses, Olga Knipper, and would marry her in 1901.

Chekhov wrote his last two plays after he had been diagnosed, in 1898, with tuberculosis. The Cherry Orchard itself was written over a period of more than two years, from early 1901 to late 1903, during which Chekhov was often in doctor-imposed exile from his wife and friends in Moscow, on the Mediterranean island of Yalta, in order to spare his ailing lungs.

The germination of The Cherry Orchard probably came from numerous and diverse sources, over a longer period of time than that for any of Chekhov's other works. Chekhov had known cherry trees from his childhood days in Taganrog, before they were all cleared as a result of Alexander's liberal economic policies which encouraged development of the Russian hinterland. Also, Chekhov had himself planted a cherry orchard on an estate in Melikhovo that he purchased in 1892; he lost the estate a short while later, and the new owner cut down the cherry trees. Much of the intellectual discussion in The Cherry Orchard is distinctly influenced by Chekhov's wide reading in literature, philosophy, and the natural sciences, especially Darwin's Origin of the Species (first published only some forty years earlier) and Marxist and socialist philosophy (though Chekhov himself was not himself a member of any revolutionary movements).

Read more about a work that could have influenced Chekhov, Karl Marx’s Das Kapital.

Chekhov had initially intended his last play to be a comedy, a vaudeville in fact, and though he may have given up that last idea he still subtitles his play A Comedy in Four Acts. Unfortunately for Chekhov, the most common reaction to the play was typified by his wife: "by the fourth act I burst out sobbing". Stanislavsky, the play's director, decided to interpret the play as a drama, against Chekhov's wishes. The debate over whether the play is in fact a comedy or a drama still goes on to this day.

The initial reception of the play ranged from the indifference of Maxim Gorky, who thought the play's story to be completely insignificant, to the loathing of Ivan Bunin, who attacked the play for being unrealistic in its depiction of both the central aristocratic family and the outrageously oversized cherry orchard. But it was also praised as one of Chekhov's best works, and possibly his best play. The Russian Symbolist poets saw the play as a narrative poem mourning the loss of beauty in the world, and thus saw Chekhov as a kindred spirit. The Bolsheviks would interpret the play as a harbinger of the 1917 revolution, because of Trofimov's speeches (many of which were censored by the Tsarist regime for the 1904 perfomance). Many noticed and applauded its new formal innovations in terms of the use of the empty stage, lost dialogue and its mixing of comic and tragic elements. But many saw the play as undeniably tragic, focusing on Ranevsky's downfall as the important element of the story.

Chekhov's critical reception outside of Russia was mixed, partly due to translation problems and the play's unique "Russian-ness", which Chekhov himself foresaw as being impossible for any foreign audience to overcome. Many foreign readers and viewers faulted the play for being unheroic, negative, and devoid of plot. But no less a figure than George Bernard Shaw said that "hearing Chekhov's plays make me want to tear up my own", and Chekhov's drama has gained increasing acceptance and praise over the course of the last century. Chekhov managed to attend The Cherry Orchard's opening night gala at the Moscow Arts Theatre on January 17th, 1904, his forty-fourth birthday. The night was also intended to celebrate his 25th year in literature; but the sight of the ill, dying Chekhov, now in the last stages of his disease, was not a cause for celebration. He remained in Moscow for the last few months of his life, finally succumbing to tuberculosis on July 1st of that same year, a few days after the The Cherry Orchard's first publication.