Anton Chekhov
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100 free Anton Chekhov trivia questions with answers — literature quiz, new questions added Oct 2026.
Anton Chekhov treated peasants for free, censused a penal island, wrote a play in a fortnight and walked out of his own premiere when the audience booed. Then Stanislavski's Moscow Art Theatre revived The Seagull and the doctor from Taganrog became, with Ibsen and Strindberg, one of the founders of modern drama. He died at 44 with a glass of champagne in his hand and came home to Moscow in a railway car meant for oysters. These 100 questions cover the four great plays, the stories and the life. Easy ones ask about his medical career, Chekhov's gun, tuberculosis and the Three Sisters' Moscow; the middle reaches Olga Knipper, Melikhovo, Lenin's reaction to Ward No. 6, Lopakhin, Astrov, the Pomeranian and the fifteen-year bet; the hard tier wants Badenweiler, Tomsk, Grigorovich's letter, Vera Komissarzhevskaya, The Wood Demon, Selivanov and the Pushkin Prize. There are adaptation questions too: Drive My Car, Olivier's Three Sisters, Carver's Errand and Shaw's Heartbreak House. Every answer is cited to a page we checked, with a short explanation so you learn something even when you miss. Play it solo or print it for a theatre night.
30 of 100 questions with answers and explanations. Play the quiz
Q 01Besides writing, what was Anton Chekhov's profession?
Physician
Physician: "Medicine is my lawful wife and literature is my mistress," he wrote, and he went on treating the poor free of charge.
Q 02In which port city on the Sea of Azov was Chekhov born in 1860?
Taganrog
Taganrog: his father ran a grocery there and conducted the church choir. When the business failed the family fled to Moscow, leaving sixteen-year-old Anton behind to finish school.
Q 03After The Seagull was booed, Chekhov vowed never again to do what?
Write plays
Write plays: "I shall never either write plays or have them acted," he told a friend the next day. Three Sisters and The Cherry Orchard were still to come.
Q 04Which director's Moscow Art Theatre revived The Seagull in 1898?
Konstantin Stanislavski
Konstantin Stanislavski had to be talked into it by his co-founder Vladimir Nemirovich-Danchenko. The triumph made the company's name, and it took a seagull as its emblem.
Q 05Chekhov told writers that anything hung on the wall in the first chapter must be used later, naming what as his example?
A rifle
A rifle: "If it's not going to be fired, it shouldn't be hanging there." The rule, now known as Chekhov's gun, says every element of a story must earn its place.
Q 06Which disease killed Chekhov in 1904 at the age of 44?
Tuberculosis
Tuberculosis: he first coughed blood in his mid-twenties but made light of it for years, begging a brother who saw a bloodied handkerchief not to tell their mother and sister.
Q 07Dying in a German spa town in 1904, Chekhov drained a final glass of what?
Champagne
Champagne: "It's a long time since I drank champagne," he said at Badenweiler in the Black Forest, then emptied the glass, lay down on his left side and died.
Q 08Chekhov's body was carried to Moscow in a refrigerated railway car meant for what?
Oysters
Oysters: the detail outraged Maxim Gorky, and in Moscow some of the thousands of mourners followed a general's funeral procession by mistake, to the sound of a military band.
Q 09Whom did Chekhov marry quietly in 1901?
Olga Knipper
Olga Knipper, a leading actress of the Moscow Art Theatre: he had a horror of weddings, so they married almost in secret, and her work kept her in Moscow while his health kept him in the south.
Q 10Chekhov wrote that he wanted a wife who, like which celestial body, would not appear every day?
The moon
The moon: his other condition, set out in 1895, was that she live in Moscow while he lived in the country. Six years later he got just such a marriage.
Q 11In 1890 Chekhov travelled across Siberia to take a census of the convicts on which penal island?
Sakhalin
Sakhalin: he spent three months there on his own initiative and at his own expense, questioning thousands of convicts and settlers for his census.
Q 12Chekhov famously called which Siberian city "a very dull town" with dull inhabitants?
Tomsk
Tomsk had its revenge in 2004 with a bronze caricature of a barefoot Chekhov in a silly hat, shown as seen "through the eyes of a drunk lying in a ditch".
Q 13The young Chekhov signed comic sketches as "Antosha Chekhonte" and as "Man Without" what?
Spleen
Spleen: "Man Without Spleen" was one of a string of jokey signatures on the daily sketches he wrote to pay his tuition and keep his bankrupt family.
Q 21Which revolutionary believed that reading Chekhov's Ward No. 6 had made him one?
Vladimir Lenin
Vladimir Lenin: "I absolutely had the feeling that I was shut up in Ward 6 myself!" he is said to have remarked. In the story the hospital's own doctor ends up admitted as a patient.
Q 22The Seagull's character Trigorin is a famous what?
Story writer
Story writer: Trigorin never stops taking notes, and on seeing a shot gull he jots down a plot about a man who destroys a girl out of sheer boredom, then does much the same to Nina.
Q 23In The Seagull, who is Arkadina's son, the symbolist playwright?
Konstantin Treplev
Q 14A veteran novelist wrote to the young Chekhov, "You have real talent", and urged him to do what?
Write less
Write less: Dmitry Grigorovich told him to stop dashing off sketches and respect his gift. Chekhov replied that the letter had struck him "like a flash of lightning".
Q 15Chekhov's story collection At Dusk won which honour in 1888?
The Pushkin Prize
The Pushkin Prize, awarded by the Academy of Sciences: only two years earlier Chekhov had still been dashing off comic sketches for the newspapers under jokey pen names.
Q 16Chekhov's long friendship with his right-wing publisher Alexey Suvorin cooled over which French scandal?
The Dreyfus affair
The Dreyfus affair: Chekhov backed Dreyfus and Zola and objected to the anti-Semitic attacks on them in Suvorin's newspaper.
Q 17Asked by a Moscow theatre manager for a play in 1887, Chekhov delivered which four-act drama within a fortnight?
Ivanov
Ivanov: he sent each act off for rehearsal as he finished it, then complained that the actors "do not know their parts and talk nonsense".
Q 18At which estate did Chekhov build a lodge in the orchard and begin writing The Seagull?
Melikhovo
Melikhovo: he threw himself into the estate, planting trees he tended, his brother said, as though they were his children, and building three village schools nearby.
Q 19Chekhov's Crimean villa, where he wrote his last two plays, is known by what name?
The White Dacha
The White Dacha: he kept dogs and tame cranes there and received Tolstoy and Gorky, yet he called the place his "hot Siberia" and was always relieved to get away.
Q 20Chekhov told Ivan Bunin that people might keep reading him for how many years?
Seven
Seven: asked why, he amended it to "seven and a half", and added that he himself would live for fewer, perhaps six. He is still read more than a century later.
Konstantin Treplev shoots a seagull and lays it at Nina's feet. In the play's last moments he shoots himself offstage while the others sit playing lotto.
Q 24Which Chekhov story follows a lost mongrel dog who is taken in and trained for the circus ring?
Kashtanka
Kashtanka: on her circus debut she hears her old master's boy shout her name from the gallery and bolts back to the drunken owner she had lost.
Q 25At The Seagull's hostile premiere, what happened to the actress playing Nina?
Lost her voice
Lost her voice: Vera Komissarzhevskaya had moved those watching to tears at rehearsal. Chekhov left his seat and spent the last two acts behind the scenes.
Q 26Chekhov insisted The Seagull was what kind of play?
A comedy
A comedy: "It's a comedy," he wrote while drafting it, with "little action, tons of love". It ends with a gunshot offstage and a suicide.
Q 27Uncle Vanya is a reworking of which earlier Chekhov play?
The Wood Demon
The Wood Demon: he wrote it at an act a day for a friend's theatre, then took it off the stage dissatisfied. Reworked years later, its suicide became Vanya's botched shooting.
Q 28In Uncle Vanya, what was Serebryakov's career before he retired to the estate?
University professor
University professor: when the retired great man announces he will sell the estate, Vanya snaps, chases him with a pistol and fires at him twice, missing both times.
Q 29Which character in Uncle Vanya is the country doctor obsessed with the destruction of forests?
Astrov
Astrov is loved without hope by Sonya while he falls for Yelena, the old man's young wife, who takes one of his pencils as a keepsake when she leaves.
Q 30Which Japanese film, a 2022 Oscar winner, centres on a staging of Uncle Vanya?
Drive My Car
Drive My Car: its widowed director runs his lines on the road, listening to tapes of the play recorded by his late wife, as he prepares a multilingual production in Hiroshima.