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Ginsberg credits the Beat writer Herbert Huncke with transmitting the notion in the late 1940s through autobiographical reminiscences, later anthologized as The Evening Sun Turned Crimson. In one story the teenage Huncke watched the police bust a hermaphrodite junkie in a seedy hotel. "The tolerance of the kid was juxtaposed with the brutality of the cops," says Ginsberg. "The sympathetic observer, Huncke, became an exemplary illustration of what was hip." Huncke's own take on the idea is a bit darker. "It meant," he recalls, "a certain awareness of everything most people were frightened of speaking of, or of admitting to knowing." No wonder then that hip unfolded largely through the work of the usual suspects -- not just blacks but also Jews, gays and a few disaffected Wasp refugees -- people whose view of things was off-center by definition.
Further fine-tunings of what hipness might mean became an offhand intellectual pursuit of the '50s. In a commentary on his much discussed 1957 essay, The White Negro, Norman Mailer distinguished between the lower-class origins of the people he termed "hipsters" and the middle-class, college- educated, moralizing Beats. But he figured they both shared "marijuana, jazz, not much money and a community of feeling that society is the prison of the nervous system."
From its early days, hipness had its aboveground successes -- the movies of James Dean, the comedy routines of Mort Sahl or Mike Nichols and Elaine May. But it took the full emergence of the baby boomers in the '60s to make hipness a force in mass culture. The hipster's stylish alienation was irresistible to youth, for whom style is the best defense against anxiety and alienation is the natural state. For suburban teens in particular, hipness became what romance novels were for Madame Bovary: an antidote to the featureless local realities. In subdivisions where the lawn sprinklers went back and forth, back and forth -- the metronomes of the trudging suburban eternity -- a Bob Dylan album and a late-night movie performance of Putney Swope could seem like blows against the Empire.
So the boomers armored themselves in hip -- after substituting rock for jazz -- in the hope, perhaps, that the right attitude and the right wardrobe might protect them from mortality itself as they moved through the years. By the time the boomers got to Woodstock, an event that immensely overran the commercial calculations that spawned it, it was possible to believe an entire countercultural universe was being born.
And at that very moment, in the very heart of downtown, the figure who would crucially assist in its undoing was adjusting his silver wig. Through most of the '60s, Andy Warhol had epitomized an arctic cool so detached it could give equal attention to soup cans and electric chairs. But Warhol's indifference was incomplete. There was never an artist more starstruck and money mad. Just three months after Woodstock, in November 1969, he published the first issue of Interview, his monthly that would lump together '40s screen goddesses, lustrous Europeans of vaguely aristocratic background and the very latest shoe designers. By virtue of the fact that Warhol had turned his placid gaze their way, the imprimatur of hip was attached to them all.