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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. Crime and Punishment by Fyodor Dostoevsky (1866). In the peak heat of a St. Petersburg summer, an erstwhile university student, Raskolnikov, commits literature’s most famous fictional crime, bludgeoning a pawnbroker and her sister with an axe. What follows is a psychological chess match between Raskolnikov and a wily detective that moves toward a form of redemption for our antihero. Relentlessly philosophical and psychological, Crime and Punishment tackles freedom and strength, suffering and madness, illness and fate, and the pressures of the modern urban world on the soul, while asking if “great men” have license to forge their own moral codes.
3. Pale Fire by Vladimir Nabokov (1962). “It is the commentator who has the last word,” claims Charles Kinbote in this novel masquerading as literary criticism. The text of the book includes a 999-line poem by the murdered American poet John Shade and a line-by-line commentary by Kinbote, a scholar from the country of Zembla. Nabokov even provides an index to this playful, provocative story of poetry, interpretation, identity, and madness, which is full to bursting with allusions, tricks, and the author’s inimitable wordplay.
4. Clarissa by Samuel Richardson (1747–48). This long epistolary novel —full of sexual tension, violence, and psychic conflict —tells the tale of the virtuous Clarissa Harlowe and her rakish suitor, Robert Lovelace. Disowned by her family, confined in a brothel and raped, Clarissa pays a high price for her morality. Yet she accepts her fate with a moving acceptance in this landmark of English realistic fiction.
5. Mrs. Dalloway by Virginia Woolf (1925). This masterpiece of concision and interior monologue recounts events in the life of Clarissa Dalloway, a delicate, upper-class London wife and mother, as she prepares for a party at her home on a single day in June 1923. In a parallel subsidiary plot, a shell-shocked World War I veteran Clarissa encounters spirals into suicide rather than submit to soul-stealing experimental psycho therapy. The novel explores questions of time, memory, love, class, and life choices through Woolf’s intricate melding of points of view and powerful use of flashback.
6. The Decameron by Giovanni Boccaccio (1351–53). The Big Chill meets the Black Death when a group of seven women and three men leave Florence to escape the plague of 1348. To entertain themselves, they tell stories according to topics selected by that day’s appointed “king” or “queen.” Like the plague, the hundred tales, mostly of love and deceit, leave no strata of society unscathed, and many of them are delightfully bawdy and irreverent. Have you heard the one about the monk who seduced a woman by claiming to be the angel Gabriel?
7. Hedda Gabler by Henrik Ibsen (1890). Like Anna Karenina and Emma Bovary, Hedda Gabler is trapped in a loveless marriage, which she entered into for security and cannot leave for fear of scandal. Though she is “crowing for life,” societal norms constrict her, making Hedda a manipulative and frustrated woman. The appearance of her former lover —a brilliant, debaucherous writer —unspools a string of betrayals that end in death in this feminist play that showcases Ibsen’s ability to dramatize the burning social issues of his day.
8. The Great Gatsby by F. Scott Fitzgerald (1925). Perhaps the most searching fable of the American Dream ever written, this glittering novel of the Jazz Age paints an unforgettable portrait of its day — the flappers, the bootleg gin, the careless, giddy wealth. Self-made millionaire Jay Gatsby, determined to win back the heart of the girl he loved and lost, emerges as an emblem for romantic yearning, and the novel’s narrator, Nick Carroway, brilliantly illuminates the post–World War I end to American innocence.
9. The Wind-Up Bird Chronicle by Haruki Murakami (1994). A cross between Dante’s Inferno, Through the Looking Glass, and Catch-22, this novel depicts the bizarre and often inexplicable journey of Japanese Everyman Toru Okada, whose missing cat prompts the disappearance of his wife, encounters with psychics and call girls, days huddled in meditation at the bottom of a well, and the breathtakingly graphic depiction of a man being skinned alive.
10. A Heart So White by Javier Marías (1994). Juan knows only this about his shady, twice-widowed father: before marrying Juan’s mother, he had wed her older sister, who committed suicide shortly after the ceremony. As Juan’s new wife becomes his father’s confessor, eliciting troubling truths, his own experiences begin to mirror those of his father in this Spanish novel that recalls the work of Henry James, Marcel Proust, and Thomas Bernhard.