This list is based on the 201 tales Constance Garnett translated over the course of some seven years, totaling 13 volumes of Chekhov’s stories and novellas.
Depending on what you’re counting, there are several hundred additional Chekhov stories that aren’t included in Garnett’s selection. But many of these are just a page or two, and some are just a few paragraphs long. Some, admittedly, are full-fledged stories or even novella-length works that arguably Garnett should have included in her 13 volume set. (She might not have been aware of them: Chekhov wrote under a variety of pen names in the early days.) But IMO none of these omitted writings rank in the top 100, so you are not really missing much. See the Sources and Resources page for information about translations, additional stories, letters, etc. etc. etc.
OK, with that out of the way, here they are: The stories of Anton Chekhov, ranked in reverse order, from dead last (and damn near unreadable) to the very, very best.
A man disappears and a detective must solve the mystery. If you don’t like detective stories, you won’t like this story. If you do like detective stories, you still probably won’t like it.
A seductive woman manages to charm two men to whom she owes money. Possibly a great story but most modern readers just won’t be able to get past the antisemitism in this one–I know I couldn’t.
A charitable homeopath realizes that her patients are using her for their own purposes. Mostly this is a soapbox that Dr. Chekhov needed to stand on for a minute.
An aggressive amateur writer forces a successful playwright to listen to her work. This story is basically a writer’s revenge fantasy.
A bureaucrat drives himself practically mad trying to figure out how a stranger’s signature keeps turning up in his guest book. Not a mysterious mystery.
No. 196 – The Examining Magistrate
A doctor deduces the solution in the mysterious death of a married woman. Another “mystery” story, another yawn.
Hallucinations of a black monk disturb the life of an ambitious man. Also, the hallucination likes to debate the nature of reality.
A self-important scribbler requires absolute silence to create his art. The greatest Russian author of his generation and possibly ever takes aim at a lesser writer. Mean.
A man woos and weds a woman who irritates the living daylights out of him. This is not the Chekhov you were looking for.
A doctor cares for a dying boy and his grief-stricken mother. Sappy and soapy.
A ninny is excited to be featured in a newspaper story. Unfortunately, it’s a story about him being injured while drunk out of his mind.
A group of jurors, sequestered for the night, trade stories from life but seem not to learn from them.
A young woman’s daydreams of marital bliss turn nightmarish.
No. 188 – The Shoemaker and the Devil
A shoemaker agrees to sell his soul to the devil. Devilment ensues.
A boy is overindulged by his lackadaisical caretakers. Stomachaches ensue.
A whiny piano tuner is humiliated repeatedly after a hotel porter misplaces his boots.
No. 185 – A Troublesome Visitor
A hunter bunks down in a woodsman’s hut and soon the two men’s differing natures lead to a clash.
A father tries one trick and another to get his son to promise not to smoke cigarettes.
A cat has kittens, to the delight of the children in the house. Not a story for PETA sympathizers.
Two bumpkins stand guard over a dead body, waiting for officials to arrive. This one is vaguely interesting just because it is drawn from Chekhov’s experience as a medical examiner conducting post mortems.
A man receives a letter from a secret admirer, but the tryst is a bust. And yes, so is the story.
A shy, depressed teenager blurts out his love for an older woman. Pretty solid story that turns exceedingly unpleasant.
A pretentious writer fails to leave an impression on the world.
A lawyer bets he can live in solitary confinement for 15 years.
A happy young couple find their idyllic day in the country ruined when unexpected family visitors come to call.
An unnamed narrator relates three separate, unrelated moments of deep unease.
A lazy auditor is unconcerned when his bank goes under.
A drunken bully bullies everyone around him, drunkenly.
A man whispers “I love you” to a woman, but she only hears him on a subliminal level.
No. 172 – The Lion and the Sun
A small-town mayor flutters around a visiting dignitary, hoping to be granted a special honor.
Two boys dream of an adventurous trek to California.
A conductor is pilloried simply for doing his job.
No. 169 – A Defenceless Creature
A woman’s request for compensation on behalf of her husband is successful thanks to her relentlessness.
A shy soldier is transformed by an unexpected encounter with a woman.
A self-involved opera singer feuds with her self-important husband.
A man accused of murder unknowingly fingers the man who may be the true culprit
Having had one drink too many, a newlywed husband can’t find his way back to his train compartment where his wife is waiting for him.
An unnamed narrator recalls two strikingly beautiful women.
Two family members quarrel over religious practices and an inheritance.
Two shepherds and a bailiff trade stories about supposed treasures buried in the woods.
A retired engineer in a loveless marriage decides to raise money to help the local peasantry during a famine.
A small town erupts in a panic for no reason.
After a young man bounces a check, a family debates whether to bail him out.
A young woman languishes in the unhealthy environment of a factory town.
A beggar’s life seems to be transformed by a bit of hard advice–but is that what really changed him?
A doctor’s interest in the treatment of mental illness seems to undermine his sanity.
A boy travels from his home on the steppe to a new city, accompanied by a variety of fellow travelers.
A dispiriting visit to a government office, where nothing happens without a bribe.
A young man must bear the wrath of his angry mother when his studies go poorly.
The travails of transporting cattle to market on the railway.
A Jewish man, having converted to Christianity, tells his life story while staying at a monastery.
A princess flatters herself that she is doing good when in fact she is not helping anyone but herself.
No. 149 – The Teacher of Literature
A teacher wins the hand of a wealthy young woman, but wonders if he has made a mistake in marrying her.
An engineer recalls a misbegotten love affair that forced him to become a better person.
A child accompanies her father on a journey and it doesn’t end well.
A schoolmaster finds himself forced to renege on a job offer to a longtime subordinate.
A man falls into bed with the wife of his friend.
A group of boys and girls play cards, bicker and wait for their parents to arrive home after a party.
A voluble young writer agrees to eulogize a man he barely knew.
A man fantasizes about winning the lottery, but even in fantasy there seems to be suffering and unhappiness.
A portrait of a family on a holiday.
Two men drink too much and get lost stumbling home.
Unwilling to live the way his rich father has, a man becomes a simple laborer.
A wealthy man fails to understand the effects of poverty on the local priest, who has been tasked with opening a school.
A pair of old school friends bump into each other and discover that their careers have followed quite different paths.
No. 136 – A Story Without an End
An actor’s failed suicide spurs his neighbor, a writer, to use him as the subject for a story.
An enormous fish foils repeated efforts to trap it.
A policeman acts tough after a puppy nips someone on the street.
No. 133 – The Head-Gardener’s Story
A saintly doctor is murdered, but no one can believe that anyone could actually kill so good a man.
No. 132 – The First-Class Passenger
Chatting up a stranger on a train, an engineer laments the fact that for all his accomplishments, he is not as well known as actors, writers and the like.
A woman makes the most of a sick day, exhausting her husband in the process.
A resentful clerk dreams of avenging himself on his superiors, but he can only take out his frustrations on a cockroach.
A lawyer connives to win the heart of a married woman.
A husband is disturbed by his wife’s poor writing skills and lack of intellectual curiosity.
A retired professor looks back on his life and that of his adoptive daughter.
A doctor has a hard time getting rid of an unwelcome gift.
No. 125 – A Day in the Country
Two poor, homeless children survive a frightening storm with the help of a kindly old peasant.
A man investigates some suspicious sounds in the house in the middle of the night.
A sly writer woos an apparently rich widow, but she has grander ambitions.
Angered by his wife’s infidelity, a man shops for a gun to take his revenge.
A sour coffin maker, coming to the end of his life, regrets his rough treatment of his wife.
A hunter bumps into his wife, whom he has abandoned, and treats her cruelly.
A traveler is forced off the road in a snowstorm and finds himself in the company of a highly untrustworthy group.
A man recovers from typhus only to learn that he has infected his beloved sister.
A lost dog is taken in by a circus animal trainer.
A mother of marriage-age daughters has nothing but disdain for a rough-mannered soldier until she learns that he is single and a gentleman.
A surveyor bound for a remote village becomes convinced that his cab driver is up to no good.
The guests at a memorial service must sneak out for quick sips of vodka because the widow has banned drinking in her house.
A naive law student has a nervous breakdown after a dispiriting bar crawl through Moscow’s red light district.
Normally a sober man, Strizhin has a bit too much to drink at a party and then imbibes from the wrong bottle when he gets home.
A rich man is touched when his staff at work present him with an album, but he is unconcerned the next day when his children rip it to pieces.
A pompous academic waits in irritation for his incompetent assistant.
A wolf accidentally kidnaps a puppy during a raid on a farm.
No. 108 – A Story Without a Title
A monk’s warnings about the goings-on in a big city have the opposite effect he intended.
A father is distraught when his daughter runs off with an actor.
A pompous snob lectures a guest about the inherent inferiority of the lower classes, only to learn that his guest comes from a modest background.
No. 105 – The Death of a Government Clerk
A sycophantic clerk accidentally sneezes on his superior, and cannot apologize enough for the insult.
A retired military man grouses about life in a warm southern town.
A self-satisfied older man hires a matchmaker to find him a wife.
The life story of a woman who assumes the identities of the people she falls in love with.
A rural couple wonder about the fate of their daughter, who has married and moved to the big city.
An actor idly boasts about a romantic conquest to the wrong person.
A dying actor rues his life and wishes he had never left his hometown.
A slice of life written from the perspective of a young boy.
A family saga of a thieving, conniving clan of merchants in a factory town.
An angry wife confronts her husband’s mistress, demanding that she give up the jewelry he bought for her.
A man recalls his efforts to blackmail his childhood tutor, who had fallen in love with his older brother.
A young woman takes her hard-working husband for granted until it is too late.
A poor man stands trial for removing hardware from the railroad tracks, an act he can’t see as a crime.
A miserable married woman experiences a little happiness when attending a dance for a visiting army regiment.
A blabbermouth wife reveals a bit too much about her girls-only trip to her husband.
A man gets the heebie-jeebies after going to a seance.
A sketch of the goings-on at a street market in Moscow.
A lazy artist summering in the countryside seduces a young woman who wants to escape to the big city.
A poor man begs a government doctor to help free his brother from jail.
A weak-willed man ineffectually seeks to avenge the stain on his honor after his sister takes up with a married man.
A man living with another man’s wife betrays a secret confided in him by her son.
A flighty teenager daydreams about life and religion.
A couple eavesdrops on their daughter and her suitor, hoping to force a marriage proposal.
A political operative goes undercover as a rich man’s servant but finds himself drawn into the man’s life.
Two men make a late night visit to the local pharmacy so as to flirt with the pharmacist’s wife.
A bailiff and a shepherd worry that the natural world is being despoiled.
In a modest country inn, a man traveling with his young daughter recalls the errors he has made in his life, and hopes to rectify them in a new job on the steppe.
In a spooky house, a mother and daughter work feverishly to create a trousseau for a wedding that will never occur.
A poor family falls to ruin in what seems to be a cursed apartment building.
A dullard falls in love with his French tutor.
A drunken father receives far better treatment from his diligent son than he deserves.
Caught out in an affair, a woman nevertheless doesn’t want to grant her husband a divorce.
An errant husband fools his credulous wife and mother-in-law with an obvious lie.
A church sexton stumbles across a menacing stranger in the graveyard.
A traveler spends the night at a stranger’s home, and is kept up all night by his host’s incessant talking.
A pesky student hitches a ride with an irritated postman.
A bullying landowner delights in insulting his servant.
In a languid seaside town, a mutual dislike festers and turns into a violent confrontation.
After a long stay as a guest at a house in the country, a statistician is taken aback when the daughter of the household tells him she has fallen in love with him.
A recollection of a painful moment of childhood poverty.
A stern latin teacher fails to deal with a mouse problem.
A governess is appalled to be accused of stealing jewelry from her employers.
No. 63 – From the Diary of a Violent-Tempered Man
A comically inept academic resists marriage, but resistance is futile.
A mingy man waits too long to get his wife to the doctor’s.
A small-town family is excited to host a relative who has risen high in the world.
The frightening and confusing world of a rural hospital for the poor, as observed by a small boy.
An indolent artist courts a rich young woman against the wishes of her older sister.
No. 58 – The Head of the Family
An ill-tempered father makes life hell for his wife and family.
A dissipated young woman approaches a former lover for money, but he doesn’t even recognize her.
An architect returns to his hometown and must face up to his past.
A poor church sexton accuses his wife of witchcraft when a postman begs to come in out of a winter storm.
A cab driver, mourning his son’s recent death, searches in vain for someone to talk to about his grief.
A young servant is cruelly overworked by her thoughtless employers.
A boy writes to his grandfather, begging to be released from a cruel apprenticeship.
A soldier lies dying in a cramped sickroom on a steamship.
A pair of officials travel to a remote town to conduct an autopsy of an apparent suicide.
A philandering husband gets what’s coming to him after a servant threatens to expose him.
The host of a party accidentally spreads a malicious rumor about himself.
A landowner and a governess grimly put up with each other while fishing.
An actor nearing the end of his life visits the shabby burial spot of another actor, the man who persuaded him to devote his life to acting.
A desperately poor man must find a way to dispose of his animals before seeking shelter with a relative.
A years-long fight of two men in love with the same woman.
An impulsive young woman wonders if she has made the right decision in choosing an older man for her husband.
A child watches, confused, as a coachman woos a servant in his parent’s house.
A woman returns to her family’s decaying property on the steppe.
A gloomy bureaucrat arrives at his cottage in the country only to be ignored by his wife, who is entertaining visitors.
An impoverished prince seeks permission to hunt on the land of a rich woman he once had been linked to romantically.
A clerk breaks off relations with his girlfriend after seeing her walking with a student.
A poor seamstress endures an abusive relationship with her medical student boyfriend.
A young man, exiled to the steppe, is schooled by a harsh old man who has eked out a living in the unforgiving environment for years.
A married couple fails to aid a man in need by the side of the road, sparking a spiral of terrible luck.
A tight-fisted lawyer bargains ferociously with a midwife–as his wife is at the point of giving birth.
A small town barber is bitterly disappointed to learn that his girlfriend’s father has promised her to another man.
A choirmaster works diligently to prepare his singers for an important visitor.
A stingy father balks at providing money for his son to attend college.
A waiter in a big city must return with his wife and child to his impoverished home village after falling ill.
After longing for a woman for years, a man discovers once he wins her that she may not be what he had imagined.
A religious student relates a biblical story to two women he meets in the woods.
Three priests at very different levels in the church hierarchy approach human problems in contrasting ways.
A bored and amoral railway worker, stuck in a remote post, is jolted by the arrival of his wife’s beautiful aunt.
No. 25 – The Lady With the Dog
A married man; a married woman; an affair; love.
A bureaucrat uses his pretty young wife to advance his career, but she has plans of her own.
After a thrilling horse ride through a thunderstorm, Pyotr declares his love for Natalya, but she feels unsure of her own feelings.
A provincial shopkeeper can’t keep himself from smearing the memory of his dead daughter.
Two comically idle villagers hope to go hunting even though the season hasn’t begun.
An imperious artisan creates a religious shrine of ice and wood for Epiphany.
After an inauspicious beginning, a married couple struggles to find happiness.
New in town, a doctor is charmed by a local family, but is disappointed when the daughter declines his marriage proposal.
A runaway convict dreams, unrealistically, of living in the country.
A handsome, lazy man seduces a local woman, even though they both know it will cause trouble.
A wealthy man’s decision to build a country house leads to feuds with the local population.
A young woman overhears her husband flirting with someone and questions her marriage.
Comfortable but stifled by life in the country, a young woman strikes out for the city.
A traveling salesman tells his life story, spurring murderous fantasies among the poor women who are listening to the tale.
A doctor, grieving the recent death of his son, is persuaded to tend to a man’s sick wife, but her illness is not what it seems.
A lonely school teacher daydreams of falling in love with a local man.
The modest, admirable life of a diligent church official.
A small town holds a winter party despite brutally cold weather.
An old teacher nearing the end of his life is surprised to discover that he is old and his days are numbered.
On the holiest, most ecstatic night of the year, a simple ferryman can’t help but mourn the death of his friend.
No. 3 – (tie) The Man in the Case
A rigid old school teacher falls in love with a young woman but his ill temper gets in the way.
A hard-working man misses the chance at love.
A man achieves his life’s goals but it’s an empty victory.
A group of servants and workman sit, play cards, and worry about the fate of the master of the house, who has committed suicide.
A young woman grapples with the immense responsibilities of running a factory and the attached town.
A Chekhov Circus 