Chekhov began writing short stories during his days as a medical student at the University of Moscow. After graduating in 1884 with a degree in medicine, he began to freelance as a journalist and writer of comic sketches. Early in his career, he mastered the form of the one-act and produced several masterpieces of this genre including The Bear (1888) in which a creditor hounds a young widow, but becomes so impressed when she agrees to fight a duel with him, that he proposes marriage, and The Wedding (1889) in which a bridegroom's plans to have a general attend his wedding ceremony backfire when the general turns out to be a retired naval captain "of the second rank".

Ivanov (1887), Chekhov's first full-length play, a fairly immature work compared to his later plays, examines the suicide of a young man very similar to Chekhov himself in many ways. His next play, The Wood Demon (1888) was also fairly unsuccessful. In fact, it was not until the Moscow Art Theater production of The Seagull (1897) that Chekhov enjoyed his first overwhelming success. The same play had been performed two years earlier at the Alexandrinsky Theatre in St. Petersburg and had been so badly received that Chekhov had actually left the auditorium during the second act and vowed never to write for the theatre again. But in the hands of the Moscow Art Theatre, the play was transformed into a critical success, and Chekhov soon realized that the earlier production had failed because the actors had not understood their roles.

In 1899, Chekhov gave the Moscow Art Theatre a revised version of The Wood Demon, now titled Uncle Vanya (1899). Along with The Three Sisters (1901) and The Cherry Orchard (1904), this play would go on to become one of the masterpieces of the modern theatre. However, although the Moscow Art Theatre productions brought Chekhov great fame, he was never quite happy with the style that director Constantin Stanislavsky imposed on the plays. While Chekhov insisted that his plays were comedies, Stanislavsky's productions tended to emphasize their tragic elements. Still, in spite of their stylistic disagreements, it was not an unhappy marriage, and these productions brought widespread acclaim to both Chekhov's work and the Moscow Art Theatre itself.

Chekhov considered his mature plays to be a kind of comic satire, pointing out the unhappy nature of existence in turn-of-the-century Russia. Perhaps Chekhov's style was described best by the poet himself when he wrote:

"All I wanted was to say honestly to people: 'Have a look at yourselves and see how bad and dreary your lives are!' The important thing is that people should realize that, for when they do, they will most certainly create another and better life for themselves. I will not live to see it, but I know that it will be quite different, quite unlike our present life. And so long as this different life does not exist, I shall go on saying to people again and again: 'Please, understand that your life is bad and dreary!'"

During Chekhov's final years, he was forced to live in exile from the intellectuals of Moscow. In March of 1897, he had suffered a lung hemorrhaage, and although he still made occasional trips to Moscow to participate in the productions of his plays, he was forced to spend most of his time in the Crimea where he had gone for his health. He died of tuberculosis on July 14, 1904, at the age of forty-four, in a German health resort and was buried in Moscow. Since his death, Chekhov's plays have become famous worldwide and he has come to be considered the greatest Russian storyteller and dramatist of modern times.