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Anton Chekhov (left) and Maxim Gorky in Yalta.

Uncle Vanya is a tragicomedy by the Russian playwright Anton Chekhov published in 1899. Its first major performance was in 1900 under the direction of Konstantin Stanislavski.

Uncle Vanya is unique among Chekhov's major plays because it is essentially an extensive reworking of a play published a decade earlier, The Wood Demon. By elucidating the specific revisions Chekhov made during the revision process, including reducing the cast-list from almost two-dozen down to a lean nine, changing the climactic suicide of the The Wood Demon into the famous failed homicide of Uncle Vanya, and altering the original happy ending into a more problematic, less final resolution, critics such as Donald Rayfield, Richard Gilman, and Eric Bentley have sought to chart the development of Chekhov's dramaturgical method through the 1890s.

Uncle Vanya was published in 1899, but it is difficult to determine when the work was originally finished, or when the revision process took place. Rayfield cites recent scholarship suggesting Chekhov revisited The Wood Demon during his trip to the island of Sakhalin, a prison colony in Eastern Russia, in 1891.

• Serebryakov, Aleksandr Vladimirovich - a retired professor.
• Elena Andreyevna(or sometimes Yelena) - his young and beautiful second wife, 27 years old.
• Sofia Alexandrovna (Sonia) - his plain daughter by his first marriage.
• Voinitskaya, Maria Vasilievna - the widow of a privy councillor, mother of the first wife of the professor.
• Voinitsky, Ivan Petrovitch ("Uncle Vanya") - Sonia's uncle, and Maria Vasilievna's son.
• Astroff, Michail Lvovich - a doctor.
• Telegin, Ilya Ilyitch - an impoverished landowner.
• Marina - an old nurse.
• A Workman

Uncle Vanya is thematically preoccupied with what might sentimentally be called the wasted life, and a survey of the characters and their respective miseries will make this clear. Admittedly, however, it remains somewhat difficult to organize these concepts into a coherent theme as they belong more to the play's "nastroenie", its melancholic mood or atmosphere, than to a distinct program of ideas.

Several well-known film versions of Uncle Vanya exist.

• Dyadya Vanya, a Russian film version, adapted and directed by Andrei Mikhalkov-Konchalovsky in 1972

• A film version of the star-studded 1963 Chichester Festival stage production, directed for the stage and starring Sir Laurence Olivier ("The finest Uncle Vanya we shall ever see in English," according to one critic.)

• Country Life, an Australian adaptation, stars Sam Neill as the country doctor.

• Sir Anthony Hopkins directed and starred in August, an English film adaptation.

• A 1994 American film version, adapted by David Mamet and directed by Louis Malle, was titled Vanya on 42nd Street. It stars Wallace Shawn and Julianne Moore. This version was originally a little-known studio production, and was later adapted for the screen, where it garnered wider acclaim.

Actors who have appeared in notable stage productions of Uncle Vanya include Constantin Stanislavsky, Olga Knipper, Anthony Sher, Ian McKellen, William Hurt, George C. Scott and Trevor Eve.

• Full text of Uncle Vanya in the original Russian
• Uncle Vanya program note from 1957 San Francisco International Film Festival
• Full English translation from the Project Gutenberg collection. Translated by Marian Fell 1916

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