Some of the show's elements were derived from works of Anton Chekhov, including several character names and sibling relationships, the play's setting in a country house (in Bucks County, Pennsylvania) with a vestigial cherry orchard, the performance of an "avant-garde" play by one of the main characters (as in The Seagull), and the themes of old vs. new generations, real vs. assumed identities, the challenges of a woman growing older after successes in a career that seems to be ending, the hope and carelessness of youth, intrafamilial rivalries, and the possible loss of an ancestral home.

The original McCarter, Off-Broadway, and Broadway casts included David Hyde Pierce, Kristine Nielsen, Sigourney Weaver and Billy Magnussen.

Subsequently, the play has been produced in Alabama,[1] Alaska, Arizona, California, Colorado, Georgia, the District of Columbia, Indiana, Massachusetts, Minnesota, Missouri, Oregon, South Carolina, Tennessee,[2] Washington, Wyoming, and Toronto.

After spending their adulthood looking after their now-dead parents, neither has a job, and money is provided by their movie star sister Masha, who owns the house and pays the bills.

Vanya (who is gay) and Sonia (who is forever reminding everyone that she was adopted) spend their days reflecting on their lost chances, debating whether the grove of nine cherry trees on their property constitutes an orchard,[3][4] and bemoaning their rather Chekhovian lot in life.

This static environment is disrupted when Masha returns home, bringing with her a flurry of drama, an endless litany of insecurity, and a much younger, gorgeous, dimwitted lover named Spike.

Sonia's resentments and Masha's competitive nature begin to spark arguments, and while Vanya tries to keep the peace, he is repeatedly distracted by the preening Spike, who takes every opportunity possible to strip down and show off his muscular body.

Another interloper arrives, the neighbor's pretty niece Nina, an aspiring actress who provokes envy in Masha, lust in Spike, and sympathy in Vanya.

As Cassandra uses a voodoo doll on Masha, trying to dissuade thoughts of selling the house, Sonia receives a phone call from a man she met at the party, requesting a date.

Vanya, who is secretly writing a play inspired by Konstantin's imagined symbolist drama in The Seagull, is convinced by Nina to let her read it in front of the others.

During the reading (which stars Nina as a molecule and takes place after the destruction of the earth), Spike rudely answers a text on his phone, and dismisses Vanya's suggestion of a handwritten response.

Vanya reacts by launching into an impassioned rant, criticizing America's cultural regression in communication and media, while fondly and wistfully recalling the surroundings and memories of his childhood.

[15] On January 29, it was announced that the show would transfer to Broadway for 17 weeks beginning March 5 with its original cast under the production of Joey Parnes, Larry Hirschhorn, and John O'Boyle, in association with McCarter Theatre and Lincoln Center Theater.

[10] The original Off-Broadway and Broadway casts featured Pierce as Vanya, Weaver as Masha, Magnussen as Spike, Nielsen as Sonia, Angelson as Nina, and Grant as Cassandra.

[26][27] Hyde Pierce reunited with the show to direct the January 29 – March 9, 2014, production at Los Angeles' Mark Taper Forum by Center Theatre Group.

[34] Playwright Durang starred as Vanya alongside Marilu Henner as Masha in a production at the Bucks County (where the play takes place) Playhouse from July 17 to August 10, 2014.

[35] Theatre Royal, Bath staged the first UK production of the play in 2019, directed by Walter Bobbie and starring Janie Dee as Masha.

Following a delayed March 2020 opening due to the COVID-19 pandemic, the production played Off West End in London at the Charing Cross Theatre in fall 2021.

The production featured the original design team of Korins, Emily Rebholz, Justin Townsend, and Mark Bennett reprising their roles.

[42] Brantley noted that the work was suitable for any audience: "Even if you’ve never read a word of Chekhov, you're likely to find plenty to make you laugh: Mr. Hyde Pierce's skillfully low-key comic discomfort; Ms. Nielsen's segues from manic eruption into glazed smiling stupor; Ms. Weaver's game sendup of every self-loving, self-doubting movie queen there ever was.

[13] Isherwood noted that as Nielsen demonstrated her ability to lighten the play's stream of Chekhovian themes, "broad comic acting [was] raised to the level of high art.