Anton Chekhov's greatest plays, from Uncle Vanya to The Seagull

Zoe Paskett
Charlie Gray

“Have a look at yourselves and see how bad and dreary your lives are!”

No one sums up Anton Chekhov’s work better than the man himself. The Russian playwright and short story artiste is regarded now as one of the greatest pioneers of psychological realism.

Chekhov is never far from the London stage. With themes of dissatisfaction, missed opportunities and the meaninglessness of life, it’s just so damn relatable.

Next up, Ian Rickson directs a new adaptation of Uncle Vanya in the West End, so we have rounded up five of the playwrights greatest theatrical works.

Uncle Vanya

(Seamus Ryan)

Uncle Vanya is a reworking of a play already published a decade before. The Wood Demon was not well received, so Chekhov returned to his script to cut the character list in half, merge some of the more confusing plotlines and get shot of any happy endings (textbook Chekhov). Under the direction of Konstantin Staislavski, Uncle Vanya came to be a permanent fixture on the Moscow stage. Sonya, her uncle Vanya and Doctor Astrov live a mundane life in the countryside. The two men contemplate the futility of existence and the unrequited love of the same woman, the new wife of Professor Serebryakov, whose arrival brings up long-repressed emotions.

Toby Jones takes the title role in the latest staging of this play, with Richard Armitage playing Astrov in Conor McPherson’s adaptation in the West End.

Buy tickets for Uncle Vanya with GO London

Three Sisters

The three sisters in question are Olga, Masha and Irina Prozorov, who have moved to the countryside but obsess over their dream of returning to Moscow. Over the course of the play, all three women, dissatisfied with their lives (familiar theme?), look for ways to make themselves happy but ultimately fail. As is Chekhov’s way, the moments of action take place off-stage, leaving the audience to witness the fallout of various catastrophic events and the emotions they bring. Unsurprisingly, at the end of the play, everyone is in a worse off place than when they started.

We’ve seen a whole slew of sisters treading the London boards over the past year. Rebecca Frecknall directed a version at the Almeida in April, followed by The Maly Drama Theatre of St. Petersburg taking to the West End. The National Theatre transposed the story to 1960s Nigeria in Inua Ellams’ interpretation.

The Seagull

(Charlie Gray)

Who better to describe The Seagull than the man himself? “It's a comedy, there are three women's parts, six men's, four acts, landscapes (view over a lake); a great deal of conversation about literature, little action, tons of love.”

Opening night of The Seagull in 1896 was a complete failure. The audience was hostile, the lead actress lost her voice and Chekhov removed himself from the auditorium and went backstage for the last two acts so he didn’t have to watch it. When the play later became a success, he refused to believe people who told him of its triumph, thinking they were just being nice. The Seagull’s rise under the direction of Stanislavski, who transformed it into a tragedy, saw the play dubbed one of the greatest events in Russian theatre history.

An aspiring writer, a successful writer, an actress and a bored young woman consider hopes and broken dreams in an isolated country estate. Emilia Clarke will make her West End debut as Nina in a modernisation of the play by Anya Reiss, and directed by Jamie Lloyd.

Buy tickets for The Seagull with GO London


Middle aged-men feeling like they’d thrown their lives away is a common theme for the playwright, and here’s another one. Ivanov is in the earlier half of his output and the first of his plays to be professionally produced. Commissioned to write a comedy, Chekhov instead responded with a drama, which took only ten days to write. (He did have to subsequently rewrite it after absolutely hating its first outing, but still – ten days!)

Self-loathing and negligent office worker Ivanov is in a huge amount of debt, spiralling out of control of his own life and coping with a dying wife, while having a mid-life crisis. "I do nothing and think about nothing, but I am tired body and soul," he laments, so he runs away to party with the people to whom he owes money.

The Cherry Orchard

(Alexander Bakshy)

Chekhov’s final play, first produced just months before he died from tuberculosis, was much more difficult to write. Incapacitated by illness, he could only write one or two lines a day. It tells of an aristocratic woman who returns home prior to its auction to a former peasant. The title refers to a cherry orchard, at risk of being cut down after the house is sold, which represents the cultural change in Russia at the time: the rise of the middle class and the fall of the aristocracy.

Director Stanislavski – once again – turned the premiere production from a comedy into a tragedy, this time much to the playwright’s chagrin. He said in a letter that Stanislavski had “ruined” his play: "Anya, I fear, should not have any sort of tearful tone... Not once does my Anya cry, nowhere do I speak of a tearful tone, in the second act there are tears in their eyes, but the tone is happy, lively.” It has been staged successfully as both in the years since.