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1. Hamlet by William Shakespeare (1600). The most famous play ever written, Hamlet tells the story of a melancholic prince charged with avenging the murder of his father at the hands of his uncle, who then married his mother and, becoming King of Denmark, robbed Hamlet of the throne. Told the circumstances of this murder and usurpation by his father’s ghost, Hamlet is plunged deep into brilliant and profound reflection on the problems of existence, which meditations delay his revenge at the cost of innocent lives. When he finally acts decisively, Hamlet takes with him every remaining major character in a crescendo of violence unmatched in Shakespearean theater.
2. Lolita by Vladimir Nabokov (1955). “Lolita, light of my life, fire of my loins. My sin, my soul.” So begins the Russian master’s infamous novel about Humbert Humbert, a middle-aged man who falls madly, obsessively in love with a twelve-year-old “nymphet,” Dolores Haze. So he marries the girl’s mother. When she dies he becomes Lolita’s father. As Humbert describes their car trip —a twisted mockery of the American road novel —Nabokov depicts love, power, and obsession in audacious, shockingly funny language.
3. 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.
4. A Portrait of the Artist as a Young Man by James Joyce (1916). In this semiautobiographical novel, hero Stephen Dedalus rejects the world of his youth —Ireland in its provincialism, nationalism, Catholicism, and sexual guilt —for art. From its stream of consciousness technique to its descriptions of expatriate life in Paris, Portrait inspired nearly all the touchstones of twentieth-century modernism, the most important of which is the artist as a misunderstood god.
5. The Rime of the Ancient Mariner by Samuel Taylor Coleridge (1798). Intermingling the fantastic with the real, this long poem begins when a mariner with “long grey beard and glittering eye” asks a trio of wedding guests to hear his tale. One guest stays to learn how the mariner shot the albatross, considered an omen of good luck, and doomed his ship. Though saved from death, the mariner is condemned to walk the earth and tell his story, which may be read as a Christian allegory or as a warning against defiling nature.
6. The Sun Also Rises by Ernest Hemingway (1926). Hemingway’s first novel recounts the revels and misadventures of the expatriate community —including the introspective writer Jake Barnes and the tantalizingly elusive divorcée Lady Brett Ashley —in Paris and in Spain’s bullfighting centers. For all their wit, wealth, or social clout and despite their rounds of drunkenness and debauchery as repetitious as the sun’s daily rising, Hemingway’s jaded, morally bankrupt characters can’t get no satisfaction.
7. Adventures of Huckleberry Finn by Mark Twain (1884). Hemingway proclaimed, “All modern American literature comes from . . . ‘Huckleberry Finn.’ ” But one can read it simply as a straightforward adventure story in which two comrades of conve nience, the parentally abused rascal Huck and fugitive slave Jim, escape the laws and conventions of society on a raft trip down the Mississippi. Alternatively, it’s a subversive satire in which Twain uses the only superficially naïve Huck to comment bitingly on the evils of racial bigotry, religious hypocrisy, and capitalist greed he observes in a host of other largely unsympathetic characters. Huck’s climactic decision to “light out for the Territory ahead of the rest” rather than submit to the starched standards of “civilization” reflects a uniquely American strain of individualism and nonconformity stretching from Daniel Boone to Easy Rider.
8. Parade’s End by Ford Madox Ford (1928). Christopher Tietjens, “the last English Tory,” is an exemplar of the old order; his faithless wife Sylvia represents the new. Grounded in their relationship, this rueful modernist epic dissects the intricacies of Edwardian England and the forces unleashed by World War I that would, inevitably and necessarily, slay that genteel world.
9. 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.
10. Emma by Jane Austen (1816). The story of Miss Woodhouse —busybody, know-it-all, and general relationship enthusiast —is a comedy of manners deftly laced with social criticism. The charm largely inheres in Emma’s imperfections: her slightly spoiled maneuverings, her highly fallible matchmaking, her inability to know her own heart. Emma teeters from lovable one moment to tiresome and self-centered the next. In writing her story, Austen found an ideal venue for her note-perfect, never-equaled archness.