From Dawn to Decadence: 500 Years of Western Cultural Life (Jacques Barzun, 2000) -- an intellectual tour de force that guides the reader through one man's knowledgeable and idiosyncratic synthesis of Western culture from 1500 through the end of the 20th century.
Heretics (G.K. Chesterton, 1905) -- a compilation of witty, incisive, and irreverent literary and social criticism, much of which remains relevant. Worth reading if only for Chesterton's jaunty prose style and infectious sense of mirth. Youthful writing at its finest.
Orthodoxy (G.K. Chesterton, 1908) -- Chesterton's attempt to move beyond his criticism of others in Heresy to expound a worldview of his own. Orthodoxy lacks the sharp edge that made Heresy so enjoyable, but it makes up for that by showing a coherent alternative to modernism as a way of understanding the world.
The Unstrung Harp; or, Mr. Earbrass Writes a Novel. (Edward Gorey, 1953) -- a perfectly understated and endlessly amusing collection of every popular stereotype of the upper-class English literary life, distilled into the character of C(lavius) F(rederick) Earbrass and accompanied by brilliant and apt illustrations.
Inside U.S.A. (John Gunther, 1946) -- an account of Gunther's travels across the United States during 1944-46. Gunther, a reporter for the Chicago Sun-Times, went to every state and in each asked a variety of prominent citizens what their state was like, and who were the powers who ran it. An invaluable look at the regional diversity of America before the homogenization of television, air travel, and widespread federal regulation.
The Phantom Tollbooth (Norton Juster, 1961) -- a book for children of all ages. I first read it when I was nine, and I re-read it every few years to marvel at how much it shaped the way I look at life.
The Great Divorce (C.S. Lewis, 1946) -- a powerful allegory of the moral choices we face in daily life.
The Heart of Rock & Soul (Dave Marsh, 1989) -- I listen to popular music with a greater appreciation and understanding than I once did because of this book, in which Marsh describes what he likes about each of what he sees as the "1001 Greatest Singles Ever Made".
"The Love Song of J. Alfred Prufrock" (T.S. Eliot, 1915) -- an eloquent statement of how it feels to be 26 years old and see nothing but a murky, unpromising future ahead. Eliot hit his mark perfectly.
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