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Leo Tolstoy’s Top 5 Characters, Ranked

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There are few writers whose legacies loom as large as the page counts of their most famous works; that’s why talking Leo Tolstoy can be almost as frightening as reading his works. Just uttering the titles of War and Peace or Anna Karenina can inspire traumatized flashbacks in those who encountered these behemoths before they were ready for them. But it’s not the length of his novels that inspire many to call Tolstoy not just one of the greatest writers ever, but the greatest writer ever; in large part, that’s due to his ability to write unforgettable characters. In celebration of his 185th birthday, here are his top five.

5. Natasha Rostova, War and Peace

Natasha Rostova is an underdog. Introduced as a “black-eyed, wide-mouthed girl, not pretty but full of life,” we watch her grow from 13 years old to 28 throughout the book, and endure her share of woe and heartbreak — but she always comes back a little wiser and stronger.

4. Ivan Ilyich, The Death of Ivan Ilyich

One thing Tolstoy and his Golden Era of Russian Literature counterparts knew how to do better than anybody was write about death and dying. From the pain in his side to his deathbed, Ivan Ilyich is more than just a character; he is a symbol of all of our own fears of mortality, boiled down into a brilliant novella.

3. Pierre Bezukhov, War and Peace

When you look at these sketches by M. S. Bashilov — as well as Tolstoy’s thoughts on the artist’s first attempt to depict the character (below) — it only puts it into even clearer perspective what an outsider the illegitimate son and eventual heir to Count Kirill Vladimirovich Bezukhov’s fortune is, and why he remains one of the writer’s best-known creations: he’s about as relatable as Russian nobility gets.

“His face is good (if only there could be more of a tendency to philosophizing in his forehead – little wrinkles or bumps over his eyebrows), but his body is small – it should be wider and stouter and more massive.” — Tolstoy

2. Dmitri Olenin, The Cossacks

Tolstoy was the original rich kid who wasn’t satisfied with the wealth and power he was born into, so in 1851, he journeyed to Caucasus and joined the army to try and find a way of life different from the privileged one he had always known. Dmitri Olenin, who basically does the same thing, is in many ways his most autobiographical character, and is what makes this often-overlooked work of Tolstoy’s so important to understanding him, and the religious philosophies he would adopt throughout his life.

1. Anna Karenina, Anna Karenina

Tolstoy’s best-known and most beloved character, Anna Karenina is a beautiful aristocrat; she is also a person who just wants to be happy and in love, but can’t seem to find those things in the world she inhabits. When she can’t get what she wants, well — let’s not spoil it for those who haven’t experienced the book Dostoyevsky and Nabokov both used the word “flawless” to describe — it’s one of literature’s most famous and tragic moments.