The following genres have all had The Cherry Orchard ascribed to them by some influential critic or playwright: Comedy, Drama, Tragedy, pastoral comedy, "Chekhovian comedy." The last genre was created specifically for the play, by Donald R. Styran; the term "pastoral" is a literary term usually denoting poems that are about shepherds, but according to Beverly Hahn, a "pastoral comedy" is the closest fit in terms of genre that The Cherry Orchard can manage. The first genre on the list is what Chekhov himself considered the play to be, as reflected in the play's subtitle: A Comedy in Four Acts. But Stanislavksy, the great director of the Moscow Arts Performing Theatre where the play was first produced, disagreed. He thought the play was a drama, and directed it as such. This annoyed Chekhov to no end. Especially irksome to the playwright was the way Stanislavsky stretched out the fourth Act to forty minutes in length, in order to heighten the emotional impact of Ranevsky's final departure. According to Chekhov, the Act should have lasted no more than twelve.

There is a fine line between pathos and comedy; as Richard Peace notes, they both involve the build-up and then release of emotional tension. The difference between is often dependent upon whether we closely sympathize with a given character's predicament or whether we maintain a certain distance from that predicament. The Cherry Orchard walks a fine line between the two. Where Chekhov may cross the line from comedy to pathos is in the amount of attention he gives to Ranevsky in terms of character development. She is, next to the orchard itself, the largest presence in the play, and thus draws the attention of readers. She is a sympathetic character, and furthermore is the one character who seems to escape the irony which distances us from the rest of the characters in the play. This has prompted some critics and readers have seen Ranevsky as a tragic hero. The play's structuring of time supports this interpretation, as well; it flows from the beginning towards a fixed end-point in the future; this fixed time frame is typical of tragedy.

Others, however, have taken Chekhov's side in the debate. And even though the subject matter of the play may appear serious, we can see that Chekhov mixes both comic elements and tragic elements in the play. First of all, though the end of the play is far from upbeat, the central character Ranevsky is alive, healthy, and perhaps better off than she was before, having the chance to leave her past behind her. Secondly, there is an element of vaudeville in the play; Yephikodov is a buffoon, and when Varya hitting Lopakhin is pure slapstick. Also, it must be noted much of the humor in The Cherry Orchard does not translate nearly as well as the symbolism. Russian culture, like any culture, has its own unique sense of humor; the challenge of translating Chekhov's jokes into the English idiom may be the main reason why there have been so many translations (90), not one of which has proven to be perfectly satisfactory. And no matter how good a translation is, it will never catch, for example, the pun on Yephikodov's words when he hands his bouquet of flowers to Dunyasha in Act One; he intends to say,"allow me to communicate to you," but the word he uses in the original Russian, prisovokupit, which is a little too close to sovokupit, which means "to copulate," especially when directed towards the woman he wants to marry.