Chekhov's first large collection, Motley Stories (1886), brought him critical respect; it was followed by the collections At Twilight (1887) and Stories (1888), from which "The Steppe" earned him the Pushkin Prize. Chekhov's many hundreds of stories concern human folly, the tragedy of trivialities, and the oppression of banality. His characters are drawn with compassion and humor in a clear, simple style noted for realistic detail. In his plays, too, Chekhov emphasizes character and mood; his plots describe the desolation of lonely people and the misunderstandings that accrue from self-absorption and desperation. His focus on internal drama was an innovation that had enormous influence on both Russian and foreign writing.

An active humanitarian, Chekhov wrote The Island of Sakhalin (1890), a study of convicts' lives that helped to effect social reform; as a physician he fought two cholera epidemics. He wrote several farces related to his early stories, but his first major staged drama was Ivanov (1887). His success as a dramatist was assured when the Moscow Art Theater took his works and built superb productions, beginning with The Seagull in 1898. They followed this with his masterpieces Uncle Vanya (1899), The Three Sisters (1901), and The Cherry Orchard (1904), his last great work.

Among the finest works of Chekhov's later years are his hundreds of letters to notable contemporaries. For the final three years of his life Chekhov was happily married to Olga Knipper, an actress with the Moscow Art company. Although they were often separated, they were together at a German health resort when he died, at 44. Most of Chekhov's works are available in English. Several lesser-known works appear in Avrahm Yarmolinsky's The Unknown Chekhov (1954) and 38 previously untranslated stories were published in The Undiscovered Chekhov (1999).