Like the writers previously discussed, Chekhov is very aware of the tragic in his writing. Hamlet, for example, resonates in several of his plays. However, deciding whether Chekhov's drama is in the spirit of the tragic or the anti-tragic is much more difficult than with playwrights such as Ibsen in his middle period or Shaw. For George Steiner, ‘Chekhov lies outside a consideration of tragedy,’ but this view is much too categorical and does not take sufficient account of various affinities between Chekhov and the tragic. The root of the problem, however, is that what appear to be tragic elements in his writing interact with comedy, farce and social realism. The tragic is unable to dominate the others and may even be undermined by them.

Though Hamlet would seem to be the most important tragedy for Chekhov – it is clearly a significant presence in The Seagull (1896) – one can also see a relationship between The Seagull and Racine's Andromaque, though instead of reinforcing the connection with the tragic, it rather reveals how Chekhov distances his drama from it, both formally and philosophically. In Andromaque one character is in love with another character who is in love with a third character in a chain of frustrated desire that eventually has a tragic outcome. The tragic effect is created by a radical discontinuity between human desire and the world beyond that desire.