50 free Anton Chekhov trivia questions with answers — literature quiz, new questions added Aug 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 50 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 50 questions with answers and explanations. Play the quiz
Q 01Besides writing, what was Anton Chekhov's profession?
Physician
"Medicine is my lawful wife," he said, "and literature is my mistress."
Q 02In which port city on the Sea of Azov was Chekhov born in 1860?
Taganrog
His father ran a grocery store there and directed the parish choir.
Q 03The Seagull was booed at its St Petersburg premiere in what year?
1896
The Moscow Art Theatre revived it triumphantly two years later.
Q 04Which director's Moscow Art Theatre revived The Seagull in 1898?
Konstantin Stanislavski
His focus on psychological realism and ensemble playing drew out the text's buried subtleties.
Q 05The dramatic principle that a rifle shown on the wall must eventually fire is known as what?
Chekhov's gun
Chekhov meant that every element of a story must be necessary and the rest removed.
Q 06Which disease killed Chekhov in 1904 at the age of 44?
Tuberculosis
He had hidden the symptoms for years, afraid to let colleagues examine him.
Q 07Chekhov died in which German spa town in the Black Forest?
Badenweiler
His last words were reportedly "Ich sterbe", after which he drank a glass of champagne.
Q 08Chekhov's body was carried to Moscow in a refrigerated railway car meant for what?
Oysters
The detail offended Maxim Gorky; some mourners followed a general's funeral by mistake.
Q 09Whom did Chekhov marry quietly in 1901?
Olga Knipper
An actress at the Moscow Art Theatre, she lived in Moscow while he stayed in Yalta.
Q 10Chekhov wrote that he wanted a wife who, like which celestial body, would not appear every day?
The moon
The letter to Suvorin proved prophetic of his long-distance marriage.
Q 11In 1890 Chekhov travelled across Siberia to census the convicts of which penal island?
Sakhalin
He spent three months interviewing thousands of prisoners and settlers.
Q 12Chekhov famously called which Siberian city "a very dull town" with dull inhabitants?
Tomsk
The remark to his sister became notorious; the city later erected a mocking statue of him.
Q 13Under what pen name did young Chekhov publish many of his early comic sketches?
Antosha Chekhonte
Another pseudonym was "Man Without Spleen".
Q 21Which revolutionary said reading Ward No. 6 "made him a revolutionary"?
Vladimir Lenin
He claimed to feel shut up in the ward himself.
Q 22The Seagull's character Trigorin is a famous what?
Story writer
Stanislavski himself played the part in the 1898 revival.
Q 23In The Seagull, who is Arkadina's son, the symbolist playwright?
Konstantin Treplev
His suicide attempts, like all lurid action in Chekhov, happen offstage.
Q 24Chekhov's future wife was one of how many original members of the Moscow Art Theatre in 1898?
Q 14Whose 1886 letter saying "You have real talent" struck the young Chekhov like a thunderbolt?
Dmitry Grigorovich
He advised Chekhov to slow down and write less; the Pushkin Prize followed in 1888.
Q 15Chekhov's 1888 collection At Dusk won which honour?
The Pushkin Prize
Grigorovich pulled a few strings to make it happen.
Q 16Which newspaper magnate became Chekhov's closest friend and paid him double the usual rate?
Alexey Suvorin
His St Petersburg paper Novoye Vremya also gave Chekhov three times the space.
Q 17Chekhov wrote his play Ivanov in how long, for theatre manager Korsh in 1887?
A fortnight
He found the chaotic production "sickening" yet it was a hit.
Q 18At which estate did Chekhov build a lodge in the orchard and begin writing The Seagull?
Melikhovo
Peasants flocked there from twenty miles around for free medical treatment.
Q 19Chekhov's villa in Yalta, where he wrote his last two plays, is known by what name?
The White Dacha
He kept dogs and tame cranes there and hosted Tolstoy and Gorky.
Q 20Chekhov told Ivan Bunin that people might keep reading him for how many years?
Seven
Pressed on why, he upgraded the estimate to seven and a half.
39
She met Chekhov at rehearsals for The Seagull and married him three years later.
Q 25Which actress lost her voice playing Nina at The Seagull's hostile 1896 premiere?
Vera Komissarzhevskaya
Chekhov fled the auditorium and spent the last two acts backstage.
Q 26Chekhov insisted The Seagull was what kind of play?
A comedy
Stanislavski's subtext-heavy staging made audiences read it as tragedy instead.
Q 27Uncle Vanya is a reworking of which earlier Chekhov play?
The Wood Demon
He cut the cast from almost two dozen to nine and swapped a suicide for a botched shooting.
Q 28In Uncle Vanya, what is the profession of the retired Serebryakov?
University professor
He announces he will sell the estate that Vanya and Sonya have kept running for him.
Q 29Which character in Uncle Vanya is the country doctor obsessed with the destruction of forests?
Astrov
Sonya loves him hopelessly; he is dazzled by Yelena instead.
Q 30Which 2022 Oscar-winning Japanese film centres on a production of Uncle Vanya?
Drive My Car
Louis Malle had earlier filmed the play as Vanya on 42nd Street.