How is Beckett's Waiting for Godot similar to Chekhov's The Cherry Orchard?
Samuel Beckett's "Waiting for Godot" and Anton Chekhov's "The Cherry Orchard" are very different in style and dramatic technique, with Chekhov's play being a traditionally realistic drama and Beckett's a radically absurdist one. the main similarities, therefore, will need to be sought at a thematic level.
Both plays show an aristocracy which has become impotent and dependent on the serf (or son of serf, in the case of Chekhov) or slave (Lucky, in the second Pozzo/Lucky episode) class. In both plays, we also get a sense that routine behaviours and attitudes have become so ritualized as to become meaningless, both in the aristocratic traditions of "The Cherry Orchard" and all of the actions of the characters in "Waiting for Godot." Also, in both plays, characters expect solutions to come from outside and the solutions do not arrive.