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Following in the tire tracks of Dreiser and Lewis, much memorable fiction of the 1920s and 1930s prominently features the automobile, from F. Scott Fitzgerald’s The Great Gatsby (1925) and John Dos Passos’s The 42nd Parallel (1930) to Erskine Caldwell’s Tobacco Road (1933) and John Steinbeck’s The Grapes of Wrath (1939). Each of these quintessentially American writers portrayed driving a car down what Steinbeck called “roads of flight” as the escape route from institutional racism, stark poverty, a regimented life, or whatever else ailed you. James Agee perhaps best summed up the nation’s infatuation with the automobile in “The Great American Roadside,” a 1934 essay published in Fortune . “God made the American restive,” Agee wrote. “The American in turn and in due time got the automobile and found it good. The war exasperated his restiveness and the twenties made him rich and more restive still and he found the automobile not merely good but better and better. It was good because continuously it satisfied and at the same time greatly sharpened his hunger for movement; which is very probably the profoundest and most compelling of American racial hungers. The fact is that the automobile became a hypnosis.”

It would take reams to list all the great American novels in which the automobile plays a pivotal role. Every reader has his own favorite literary road scene, be it the superb opening of Robert Penn Warren’s All the Kings Men (1946) or Humbert Humbert’s experiencing the whole gamut of our roadside kitsch in Vladimir Nabokov’s Lolita (1955) or the declaration of Mr. Shiftlet in Flannery O’Connor’s short story “The Life You Save May Be Your Own,” who declares, “The body, lady, is like a house: it don’t go anywhere; but the spirit, lady, is like an automobile: always on the move always.”

AFTER WORLD WAR II, How ever, road books that tended to embrace Booth Tarkington’s notion of the automobile as a metal demon began to appear. Indisputably the most surly was Henry Miller’s The Air Conditioned Nightmare (1945). Miller, who had been living in Paris as the notorious expatriate author of Tropic of Cancer , had returned to America for a spell and decided to travel the despised nation of his birth by automobile. He lambasted everything from supermarkets to hairstyles to exhaust fumes—to cars themselves, which got a swift kick after the author chugged up a California mountain pass on his way to San Bernardino: “Everything but the ocean seems jammed into this mile-high circus at sixty miles an hour. It wasn’t I who got the thrill —it was a man inside me trying to recapture the imagined thrill of the pioneers who came through this pass on foot and horseback. Seated in an automobile, hemmed in by a horde of Sunday afternoon maniacs, one can’t possibly experience the emotion which such a scene should produce in the human breast.” Miller denounced the automobile as a “symbol of falsity and illusion.”

His bitterness toward the car echoes into the present. Miller was prophetic in describing the auto as a scourge of nature rather than a tonic for the soul. His disaffection is sideswiped by Jack Kerouac in On the Road (1957), the best-known highway book of the century, which is both a protest against Eisenhowerera conformity and a self-celebration of Whitmanesque proportions. The prose is pure high-octane wanderlust; the reader doesn’t even have to know what Kerouac meant by “the mad road, keening in a seizure of tarpaulin power” to understand this portrait of a beat generation questing for the heroic. On the Road ’s language is exhilarating, and Kerouac’s societal indictments get lost in his romantic rush to blaze across America in a big, shiny, tail-finned car, listening to Dizzy Gillespie blow jazz on the radio, eating pie ala mode in Iowa, talking about the Old West in Manhattan, shooting pool in San Francisco’s Chinatown, working as a migrant laborer in California, drinking cervezas in Old Mexico, and all the while searching for “It”—“the moment when you know all and everything is decided forever.” A Hoosier Holiday had primed its readers to take automobile sightseeing vacations; On the Road exhorted them to reconsider their lives.

The book made Jack Kerouac forever synonymous with tales of the highway, and few other novels can have caused so many restless people to wander their nation contemplating the nature of existence. Not surprisingly, much of the best road literature of the 1960s and 1970s owes a debt to Kerouac. Robert M. Pirsig’s Zen and the Art of Motorcycle Maintenance (1974), for example, is a classic hybrid of Thoreau and Kerouac, a road guide to spiritual recuperation that can be seen as an early progenitor of so-called New Age literature. But as Pirsig traveled America, it was a dog-eared copy of Waiden he packed in his motorcycle’s saddlebags because “it can be read a hundred times without exhaustion.”