Chekhov referred to The Three Sisters as a "drama," preferring to avoid the more confining labels of either "comedy" or "tragedy," although later critics have argued for both of those labels. It is one of the four major plays that he wrote at the end of his life. Chekhov was an accomplished fiction writer, one of the one of the most influential short story writers of all time. At the time that his plays were being produced there was some criticism that his dramas too closely resembled the style of fiction. Traditionalists found the action too cramped and the characters too inexpressive, noting that there were too many people on the stage at any one time, doing nothing, for audiences to be able to register the significance of it all. Contrary to expectations, though, Chekhov's plays were very popular in Moscow, where they were staged by the famous Moscow Art Theatre under the direction of Constantin Stanislavsky.

The Three Sisters was the first play that Chekhov wrote specifically for the Moscow Art Theatre, having experienced commercial success in his previous collaborations with the company, The Seagull and Uncle Vanya. Like many of Chekhov's works, it is about the decay of the privileged class in Russia and the search for meaning in the modern world. In the play, Olga, Masha, and Irina are refined and cultured young women in their twenties who were raised in urban Moscow but have been living in a small, colorless provincial town for eleven years. With their father dead, their anticipated return to Moscow comes to represent their hopes for living a good life, while the ordinariness of day-to-day living tightens its hold. First performed in 1901, The Three Sisters is a perennial favorite of actors and audiences.