The debate over whether The Cherry Orchard is a comedy or a tragedy began with Chekhov himself and his director (and sometimes friend) Konstantin Stanislavsky.
Chekhov insisted that the play was a comedy, even a farce, highlighting the absurdity of the characters’ inability to act in the face of inevitable change. He saw humor in their contradictions—Lyubov’s reckless spending, Leonid's pompous speeches, and Alexander's inability to propose to Varya. However, when Stanislavsky directed the play at the Moscow Art Theatre in 1904, he treated it as a tragedy, emphasizing the sorrow of the family losing their beloved estate.

Chekhov was deeply frustrated by this interpretation, feeling that Stanislavsky had made the play too sentimental. Chekhov himself was struggling with illness and nearing the end of his life when he traveled to Moscow just before the production opened in 1904.
When he saw the show onstage opening night, including Stanislavsky in the role of Leonid Gaev, he reportedly exclaimed in distress, believing the humor had been lost. He even struggled to face the audience and their applause following the opening performance.
This disagreement continues today, as directors, performers, and scholars argue over whether the play is tragic, comic, or a perfect blend of both.