Where to Start with Anton Chekhov: A Reading Guide
Where to start with Anton Chekhov — how to approach The Cherry Orchard and his essential short stories. A complete reading guide to the Russian master.
Anton Chekhov (1860–1904) was the Russian physician and writer who is generally regarded as the greatest short-story writer of the nineteenth century and one of the four great dramatists of Western theatre (alongside Ibsen, Strindberg, and Shakespeare). Chekhov practised medicine throughout his writing life — ‘medicine is my lawful wife and literature my mistress,’ he wrote — and his dual perspective as scientist and artist produced fiction and drama of unusual observational precision and emotional intelligence. His four major plays (The Seagull, Uncle Vanya, Three Sisters, and The Cherry Orchard) defined the dramaturgy of psychological realism; his short stories created the modern short story as a form.
Where to Start: The Cherry Orchard (1904)
The essential Chekhov for theatre — and his most perfectly realised play. The Ranevskaya family returns to their Russian estate in spring: Madame Ranevskaya and her daughter Anya from Paris, where they’ve been living on dwindling funds; her brother Gaev, ineffectual and attached to a childhood bookcase; various servants and neighbours. The estate, which includes the famous cherry orchard, is to be auctioned for debts.
Lopakhin, a merchant whose family were serfs on the estate, has a practical solution: cut down the cherry orchard and develop the land for summer cottages. The money would save the family. The family cannot do it — the orchard represents everything they are, or were. They talk, they drift, they fail to act. The estate is sold at auction. Lopakhin buys it. In the final act, the family departs while the sound of axes cutting the cherry orchard begins.
Chekhov called it a comedy. The comedy is in the gap between the characters’ pretensions and their actions, their failure to see clearly, their inability to change. The sadness is in the same material: these are real people, fully rendered, losing everything that gave their lives its particular texture. The play holds both simultaneously.
For readers approaching Chekhov through his drama, The Cherry Orchard is the ideal starting point — better than The Seagull (his masterwork but harder to follow in reading) and more representative than the equally great Three Sisters.
Where a New Reader Should Begin
For a reader new to Anton Chekhov, the ideal entry point depends on whether you wish to begin with his celebrated plays or his masterful short stories, for he is a supreme master of both, but The Cherry Orchard, his final and most famous play, offers a superb introduction to his distinctive art. The Cherry Orchard exemplifies Chekhov’s revolutionary approach to drama, the subtlety, the indirection, the attention to mood and the ordinary, and the blend of comedy and sadness that mark his work, in the story of a family losing their estate as an old order gives way to a new. As an entry point, it offers a full and accessible expression of Chekhov’s distinctive genius, the understated drama, the rich human sympathy, and the bittersweet blend of comedy and melancholy. For readers who prefer to begin with his fiction, his short stories offer an equally superb introduction to his mastery of that form. It welcomes the newcomer with its subtlety, its humanity, and its bittersweet beauty, drawing the reader into Chekhov’s distinctive vision. For the newcomer, then, The Cherry Orchard is an ideal starting point, with his short stories an equally fine alternative.
What to Expect as a New Reader
As a new reader, you can expect Chekhov’s work to be subtle, understated, and deeply humane, marked by attention to the ordinary, a blend of comedy and sadness, and a revolutionary indirection. You can expect subtlety and indirection, for Chekhov transformed drama and fiction by moving away from dramatic incident and overt action toward the quiet, indirect rendering of mood, character, and the texture of ordinary life. You can expect attention to the ordinary, for Chekhov found his material in the everyday lives, longings, and disappointments of ordinary people, rendered with extraordinary sympathy and insight. You can expect a bittersweet blend of comedy and sadness, for Chekhov’s work mingles the comic and the melancholy, finding both humor and pathos in human life, and refusing simple categories. You can expect deep human sympathy and a profound understanding of the human heart. Expect, in short, subtle, understated, and deeply humane work, marked by attention to the ordinary and a bittersweet blend of comedy and sadness, a profound introduction to Chekhov’s revolutionary art.
Going Deeper After Your First Book
Once you have encountered Chekhov’s art in The Cherry Orchard or his short stories, the reader who wishes to go deeper can explore the full range of his work in both drama and fiction, for he is a supreme master of both forms. His other great plays continue his revolutionary approach to drama, the subtlety, the attention to mood and the ordinary, and the blend of comedy and sadness, while his many short stories represent one of the supreme achievements in that form, rendering the lives and inner experiences of ordinary people with unmatched subtlety and insight. Reading across both his plays and his stories deepens your appreciation of Chekhov’s distinctive genius, the understated drama, the deep human sympathy, and the bittersweet beauty that mark all his work. His characteristic qualities run through both forms, and the reader who has been moved by one will find the same genius in the other. Building your reading journey through Chekhov’s work is a matter of exploring both his celebrated plays and his masterful short stories. The reader who begins with The Cherry Orchard and continues through his plays and stories will encounter one of the supreme masters of both drama and fiction.
Reading Anton Chekhov
Begin with The Cherry Orchard for the drama. For the short stories — which many consider his most important work — start with ‘The Lady with the Dog,’ ‘Ward No. 6,’ and ‘The Darling.’ His four major plays can be read in any order.
For the full Anton Chekhov bibliography, reviews, and biography, visit the Anton Chekhov author page on Editors Reads.
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Frequently Asked Questions
Where should I start with Anton Chekhov?
For Chekhov's drama: The Cherry Orchard (1904) is the recommended starting point — his final play, a comedy about an aristocratic family losing their estate that is simultaneously a lament for a vanishing social world. For Chekhov's fiction: his short stories are the essential work — particularly 'The Lady with the Dog,' 'Ward No. 6,' 'The Bishop,' 'Gooseberries,' and 'The Darling.' Chekhov is considered the greatest short-story writer in any language by many writers; his plays are his second major achievement.
What is The Cherry Orchard about?
The Cherry Orchard follows an aristocratic Russian family returning to their estate in the spring of 1904 — the estate that includes a famous cherry orchard that is about to be sold for debt. A merchant offers to save them by cutting down the orchard and developing the land; the family cannot bring themselves to do it. The play observes their paralysis and their eventual displacement with equal compassion and irony. Chekhov described it as a comedy; Stanislavski staged it as a tragedy; most productions find the aching space between.
Why are Chekhov's short stories considered so important?
Chekhov invented what is now the dominant mode of the literary short story: the plotless story that renders a state of being rather than a sequence of events, that ends not with resolution but with a deepened understanding of the situation. Before Chekhov, stories ended with something happening; after Chekhov, the best stories end with a revelation that something has always been happening, unseen. His influence on the short story as a form is comparable to Joyce's influence on the novel: essentially every serious short story written after him is in some relationship to his method.
Which Chekhov short story collection should I start with?
Most collections of Chekhov's stories are good; the key is to read many of them rather than a single carefully curated selection. Penguin's Chekhov: The Complete Short Stories is the most comprehensive; Richard Pevear and Larissa Volokhonsky's translation (Bantam, 2000) is widely considered the best recent translation. Among individual stories to start with: 'The Lady with the Dog,' 'Ward No. 6,' 'The Student,' 'The Darling,' and 'Gooseberries' — five stories that represent his full range.
