This book provides an in-depth analysis of the writer’s four great plays: The Seagull, Uncle Vanya, The Three Sisters, and The Cherry Orchard in their cultural context. This book explores how Chekhov’s historical situation as a non-aristocratic writer gave him an intense awareness of his relationship to the past. Chekhov had a very literary imagination and thus an essential feature of his work is the way he used intertextuality to incorporate and react to the work of his predecessors. Chekhov’s plays therefore lend themselves to analysis that uses Harold Bloom’s theory of the anxiety of influence. Applying these principles make it possible to give coherence to Chekhov’s. The anxiety of influence was a pervasive factor in Chekhov’s evolution, and explains why Chekhov used intertextuality more frequently, and to greater effect, than any of his contemporaries. Close study of Chekhov’s four great plays shows that they have a hitherto unrecognized stylistic alternation. ‘Chekhov the Anxious Playwright’ makes extensive use of recent Russian scholarship (including dissertations) on Chekhov and synthesizes it with Western scholarship to produce a general understanding of his plays in their cultural context. It will be the first major book that brings together both a wide range of scholarship and as well as literary theory to analyze Chekhov’s plays. This book will be of great interest to students and scholars in theatre history and Russian literature.