Leo Tolstoy was a bit of a mess. Honestly, that’s the first thing you need to understand if you want to actually enjoy books written by Tolstoy instead of just treating them like a homework assignment. He wasn't some stoic statue of a "Great Writer." He was a man who couldn't stop arguing with himself, a wealthy count who tried to live like a peasant, and a guy who wrote some of the longest novels in history while simultaneously claiming that art was mostly a waste of time.
It’s hilarious, really.
Most people see a 1,200-page copy of War and Peace and feel a physical sense of dread. It’s thick enough to use as a doorstop or a weapon. But if you strip away the "classic literature" pretension, you’re left with stories that feel like they were written yesterday. He captures that specific, awkward feeling of being at a party where you don't know anyone, or the weirdly quiet moment right before something terrible happens. He was the king of the "vibe check" before the term existed.
The Big Two: Why Everyone Starts Here
You can't talk about books written by Tolstoy without the heavy hitters. War and Peace and Anna Karenina. They are the suns around which everything else in his bibliography orbits.
Let's look at War and Peace first. People think it’s a history book. It’s not. Well, it is, but that’s the boring way to look at it. It’s actually a massive soap opera set against the backdrop of Napoleon trying to burn Russia to the ground. You’ve got Pierre Bezukhov—basically a big, bumbling nerd who inherits a fortune and has no idea what to do with his life. We’ve all been Pierre. Then there’s Prince Andrei, who is handsome, cynical, and utterly bored by everything until he finds himself lying in a field looking at the sky while a battle rages around him.
The book is famous for its "historical digressions." Tolstoy will be telling a gripping story about a girl falling in love, and then suddenly he’ll stop for thirty pages to rant about how "Great Men" don't actually control history and how generals are basically just guessing. It’s erratic. It’s brilliant. It’s also deeply human. He wasn't trying to be perfect; he was trying to capture the entirety of life.
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Then there is Anna Karenina. Often called the greatest novel ever written. Why? Because it’s a surgical examination of how we ruin our own lives. Anna is a socialite who has a scandalous affair, but the book isn't just about her. It’s about Levin, a semi-autobiographical version of Tolstoy himself, who spends his time worrying about farming techniques and the meaning of God. The contrast between the high-society tragedy of Anna and the mud-on-the-boots searching of Levin is where the magic happens.
The Mid-Life Crisis That Changed Everything
Around the age of 50, Tolstoy had a massive breakdown. He looked at his fame, his money, and his family and thought, "What’s the point? I’m going to die anyway." This led to what scholars call his "Confession."
If you want to understand the later books written by Tolstoy, you have to read A Confession. It’s short. It’s brutal. He talks about how he considered taking his own life because he couldn't find a logical reason to keep going. This shift changed his writing style forever. He stopped wanting to write "art" and wanted to write "truth."
This period gave us The Death of Ivan Ilyich.
If you only read one thing by Tolstoy, make it this. It’s a novella about a guy who is a mediocre judge. He’s lived a "pleasant and decorous" life. Then, he gets a weird pain in his side. He’s dying. The story follows his slow realization that his entire life—his career, his social status, his nice curtains—was a total sham. It’s terrifying because it’s relatable. It’s about the fear of having lived a life that didn't matter. It’s one of the few books written by Tolstoy that can actually make you change how you spend your Tuesday afternoon.
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The Controversial Stuff Nobody Mentions
Tolstoy got weird in his old age. He became a radical pacifist, a vegetarian, and a Christian anarchist. He started writing things that the Russian government and the Church absolutely hated.
Take Resurrection. This was his last major novel. It’s basically a massive middle finger to the legal system and the organized church. It follows a nobleman named Nekhlyudov who sits on a jury and realizes the woman being tried for murder is someone he seduced and abandoned years ago. He tries to save her, and in the process, Tolstoy takes us through the absolute filth of the Russian prison system. It’s not "pretty" like War and Peace. It’s angry.
And then there's The Kreutzer Sonata. Honestly, it’s a bizarre read. It’s a novella about a man who murders his wife out of jealousy, but it turns into a long-winded argument against sex and marriage. Tolstoy was basically arguing for total celibacy—even for married people. It caused a massive scandal. Even his wife, Sophia, was understandably annoyed by it. It shows a darker, more obsessive side of his genius that people often gloss over in favor of the "grandfatherly figure" image.
Short Stories: The Entry Point for the Rest of Us
If the idea of a 1,000-page book makes you want to nap, his short stories are where it’s at. They are tight, punchy, and usually have a "moral" that hits you like a brick.
- How Much Land Does a Man Need? — This is basically a folk tale about greed. A guy is told he can have all the land he can walk around in a day. Spoiler: He gets greedy and it doesn't end well. James Joyce called it the greatest story ever written. He wasn't wrong.
- Master and Man — A story about a wealthy landowner and his servant getting lost in a blizzard. It’s a beautiful, heart-wrenching look at sacrifice and what actually matters when you’re freezing to death.
- Hadji Murat — Written near the end of his life but published after he died. It’s about a Caucasian rebel leader. It’s fast-paced, violent, and incredibly modern in its political skepticism. Harold Bloom, the famous critic, argued it might be the best thing Tolstoy ever wrote because it’s so lean and perfect.
Why Should You Care in 2026?
We live in a world of 15-second clips and constant dopamine hits. Books written by Tolstoy demand the opposite. They demand that you sit still.
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But here’s the secret: they aren't "slow" because they're boring. They are slow because they are immersive. Tolstoy doesn't just tell you a character is sad; he describes the way the light hits the room and the specific way the character’s collar feels too tight, until you are that person.
He understood psychology before psychology was a formal discipline. He knew that we don't make decisions based on logic. We make them based on pride, lust, fear, and a desperate need to feel like we belong. Whether it's a soldier in the Crimean War (which he actually fought in, by the way) or a mother in a high-society ballroom, he gets inside their heads with a terrifying level of accuracy.
Tips for Actually Finishing These Books
If you’re going to dive into the world of books written by Tolstoy, don’t just grab the first copy you see at a used bookstore. The translation matters.
For years, Constance Garnett was the standard. She’s okay, but she can be a bit "Victorian" and tends to smooth over Tolstoy’s rougher, more repetitive edges. If you want the real experience, look for translations by Richard Pevear and Larissa Volokhonsky. They keep the weirdness intact. Or try the Louise and Aylmer Maude translations—Tolstoy actually knew them and approved of their work.
Also, stop worrying about the names. Russian names are a nightmare. Every character has a first name, a patronymic (based on their father's name), and a family name. Plus, they all have about five different nicknames. Pierre is also Pyotr Kirillovich. Natasha is also Natalya Ilyinichna. Just print out a character list and keep it as a bookmark. Don't let the names stop you from enjoying the drama.
Actionable Steps for the Aspiring Tolstoy Reader
- Start small. Don't buy War and Peace today. Buy The Death of Ivan Ilyich. It’s 60 pages. If you don't like that, you won't like the big stuff.
- Use an audiobook. If the descriptions of 19th-century farming or military strategy get tedious, listen to them while you’re driving or doing dishes. The "voice" of the story often comes through better that way.
- Watch the movies first. Seriously. Watch the 2012 Anna Karenina (the one with Keira Knightley) or the BBC's War and Peace miniseries. It gives you a mental map of who the characters are so you don't get lost in the text.
- Ignore the philosophy at first. If you’re reading War and Peace and Tolstoy starts screaming about "The Laws of Necessity," just skim it. You can go back and be a scholar later. For your first read, just follow the characters.
- Read the diaries. If you want the real tea, look up excerpts from Leo and Sophia Tolstoy's diaries. They used to give their diaries to each other to read. It was a toxic, fascinating, and deeply emotional mess that explains a lot about the tension in his novels.
Tolstoy wasn't trying to write "classics." He was trying to figure out how to be a human being without losing his mind. That's a struggle that hasn't changed in over a hundred years. When you read him, you aren't looking at a museum piece; you're looking in a mirror. It’s uncomfortable, it’s long, and it’s occasionally annoying, but it’s realer than almost anything else you’ll find on a bookshelf.
Next Steps for Your Reading List:
- Pick up "The Death of Ivan Ilyich" to see if you vibe with his philosophical side.
- Grab a copy of "Hadji Murat" if you prefer action and political tension.
- Commit to 20 pages a day of "Anna Karenina"—at that pace, you'll finish the "greatest novel ever" in about six weeks.