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1. The Divine Comedy by Dante Alighieri (1321). Dante’s poetic trilogy traces the journey of a man’s soul from darkness (The Inferno) to the revelation of divine light (Paradiso) while providing commentary and gossip about the politics and prominent families of Florence. Led in his pilgrimage through the underworld and purgatory by the Greek poet, Virgil, Dante is escorted into paradise by his early beloved, Beatrice, while learning that, in order to ascend, he must be transformed.
2. Essays by Michel de Montaigne (1533-92). Reflections by the creator of the essay form, display the humane, skeptical, humorous, and honest views of Montaigne, revealing his thoughts on sexuality, religion, cannibals, intellectuals, and other unexpected themes. His most celebrated pieces include "On Solitude," "To Philosophize Is to Learn How to Die," and "On Experience."
3. Don Quixote by Miguel de Cervantes (1605, 1615). Considered literature’s first great novel, Don Quixote is the comic tale of a dream-driven nobleman whose devotion to medieval romances inspires him to go in quest of chivalric glory and the love of a lady who doesn’t know him. Famed for its hilarious antics with windmills and nags, Don Quixote offers timeless meditations on heroism, imagination, and the art of writing itself. Still, the heart of the book is the relationship between the deluded knight and his proverb-spewing squire, Sancho Panza. If their misadventures illuminate human folly, it is a folly redeemed by simple love, which makes Sancho stick by his mad master “no matter how many foolish things he does.”
4. Tristram Shandy by Laurence Sterne (1759–67). Sterne promises the “life and opinions” of his protagonist. Yet halfway through the fourth volume of nine, we are still in the first day of the hero’s life thanks to marvelous digressions and what the narrator calls “unforeseen stoppages”—detailing the quirky habits of his eccentric family members and their friends. This broken narrative is unified by Sterne’s comic touch, which shimmers in this thoroughly entertaining novel that harks back to Don Quixote and foreshadows Ulysses.
5. Moby-Dick by Herman Melville (1851). This sweeping saga of obsession, vanity, and vengeance at sea can be read as a harrowing parable, a gripping adventure story, or a semiscientific chronicle of the whaling industry. No matter, the book rewards patient readers with some of fiction’s most memorable characters, from mad Captain Ahab to the titular white whale that crippled him, from the honorable pagan Queequeg to our insightful narrator/surrogate (“Call me”) Ishmael, to that hell-bent vessel itself, the Pequod.
6. The Brothers Karamazov by Fyodor Dostoevsky (1880). In perhaps the consummate Russian novel, Dostoevsky dramatizes the spiritual conundrums of nineteenth-century Russia through the story of three brothers and their father’s murder. Hedonistic Dmitri, tortured intellectual Ivan, and saintly Alyosha embody distinct philosophical positions, while remaining full-fledged human beings. Issues such as free will, secularism, and Russia’s unique destiny are argued not through authorial polemic, but through the confessions, diatribes, and nightmares of the characters themselves. An unsparing portrayal of human vice and weakness, the novel ultimately imparts a vision of redemption. Dostoevsky’s passion, doubt, and imaginative power compel even the secular West he scorned.
7. Madame Bovary by Gustave Flaubert (1857). Of the many nineteenth-century novels about adulteresses, only Madame Bovary features a heroine frankly detested by her author. Flaubert battled for five years to complete his meticulous portrait of extramarital romance in the French provinces, and he complained endlessly in letters about his love-starved main character— so inferior, he felt, to himself. In the end, however, he came to peace with her, famously saying, “Madame Bovary: c’est moi.” A model of gorgeous style and perfect characterization, the novel is a testament to how yearning for a higher life both elevates and destroys us.
8. Ulysses by James Joyce (1922). Filled with convoluted plotting, scrambled syntax, puns, neologisms, and arcane mythological allusions, Ulysses recounts the misadventures of schlubby Dublin advertising salesman Leopold Bloom on a single day, June 16, 1904. As Everyman Bloom and a host of other characters act out, on a banal and quotidian scale, the major episodes of Homer’s Odyssey—including encounters with modern-day sirens and a Cyclops—Joyce’s bawdy mock-epic suggests the improbability, perhaps even the pointlessness, of heroism in the modern age.
9. To the Lighthouse by Virginia Woolf (1927). The Ramsays and their eight children vacation with an assortment of scholarly and artistic houseguests by the Scottish seaside. Mainly set on two days ten years apart, the novel describes the loss, love, and disagreements of family life while reaching toward the bigger question—“What is the meaning of life?”—that Woolf addresses in meticulously crafted, modernist prose that is impressionistic without being vague or sterile.
10. The Magic Mountain by Thomas Mann (1924). Hans Castorp visits his cousin at a sanatorium in the mountains of Switzerland. Soon he too becomes ill (maybe) and checks into the hospital—for seven years. In this sanctuary, Hans and the sanatorium’s denizens endlessly debate questions of morality, politics, and culture, as the “real world” moves inexorably toward the horror of World War I. A meditation on time, an inquiry into how life ought to be lived, and an unflinching look at evil, Mann considered the ideas in his monumental novel so challenging that he said it must be read at least twice.