Which one to read first
Almost every reading list for Russian learners is either graded readers — which nobody wants to have read — or "the classics", undifferentiated, as though Chekhov's four-page sketch and Notes from Underground asked the same thing of you. Here is the honest order, measured on the texts themselves.
Start here — free, and no account
Seven Chekhov stories, easiest first. Every one is complete and unabridged.
Смерть чиновника — The Death of a Clerk
A clerk sneezes on a general, and cannot survive having done it.
Толстый и тонкий — Fat and Thin
Two childhood friends meet at a station — until they establish which of them holds the higher rank.
Хамелеон — Chameleon
A police inspector changes his mind about a dog — depending on whose dog it turns out to be. The classic on rank-worship.
Лошадиная фамилия — A Horsey Name
The general has toothache, and the name of the man who can cure it is “something to do with horses”… The most famous joke in Russian.
Злоумышленник — The Malefactor
A peasant has been unscrewing nuts from the railway line — “for fishing weights”. An interrogation that is funny and then frightening.
Студент — The Student
A cold evening, a fire, a story about the apostle Peter — and suddenly everything connects. Chekhov's own favourite.
Ванька — Vanka
Nine-year-old Vanka writes a letter “to grandfather, in the village”. The shortest and the sharpest story on the shelf — and thick with village words: save it for later, not for first.
Then the longer ones
Gogol, Turgenev and Dostoevsky, plus the Chekhov that runs longer. These are part of the library.
Мальчики — The Boys
Volodya comes home for the holidays with a mysterious friend. The escape to America is set for tomorrow.
Спать хочется — Sleepy
A thirteen-year-old nursemaid rocks somebody else's baby, night after sleepless night. One of the most frightening things Chekhov wrote.
Дама с собачкой — The Lady with the Dog
A holiday affair in Yalta that turns out, against everyone's intention, to be the central event of two lives.
После бала — After the Ball
A ball, a mazurka, and what the same man was doing at dawn.
Нос — The Nose
Major Kovalyov's nose leaves his face and is seen about Petersburg in the uniform of a State Councillor.
Шинель — The Overcoat
A small man and his great overcoat. The founding story of Petersburg clerkdom, and of Russian prose after it.
Белые ночи — White Nights
Four white nights and a morning. A dreamer meets Nastenka on the embankment and speaks to another person for the first time in his life.
Первая любовь — First Love
Sixteen years old, a dacha outside Moscow, a princess next door — and the discovery of who she really loves.
How to know if you are ready
You do not need to be. The point of a glossed reader is that the vocabulary arrives while you read rather than before. But if you want the numbers — how many words buy how much of the page — they are in how much Russian you need to read Chekhov, and the word lists are ordered accordingly.