ohn Leland may or may not have written the first history of hipness—I can't, in an admittedly casual search, find another—but it's hard to shake the thought that such a book might as well be its subject's obituary. It's like broadcasting the rituals of the lodge, or maybe spelling down all the names of the godhead. There are dozens of histories of bohemia, but that's not the same thing, although the two concepts have a large field of intersection. Bohemia started in Europe and spread around the world, but hip (Leland employs the word as both adjective and noun) is indigenously American. The word derives from the Wolof hepi ("to see") and hipi ("to open one's eyes"). The idea of hip emerged from seeds sown in Senegambia that budded in America. It has everything to do with race mixing, and it works both ways, comprising not just white people's love and theft of black style but also African American appropriations of European baggage: the pianoforte, the three-button suit, existentialism, Yiddish expressions, horn-rim glasses, the novel. And hip is occult, arcana without a heaven.

Cultural miscegenation is fundamental not just to hipness but to the United States in all its finest aspects. The fact that racial intercourse until very recently had to be carried out more or less in secret accounts for the glamorous air of danger that attached to hipness, even while the product that emerged from hip might sooner or later find its way into the canon. The effects of cultural race mixing are felt every day by every single inhabitant of the United States, although, perversely, an official line persists in admitting only the Nordic Protestant sliver of the nation's identity—see for example the recent excreta of Samuel P. Huntington. That alone might ensure the continued survival of hip, even without assistance from the marketing department and its banks of iron lungs—but I'm getting ahead of myself.

"Hip is a term of enlightenment," writes Leland. It incorporates cool, a concept that itself dates "back to a 15th-century king in the Nigerian empire of Benin who was awarded the name Ewuare, meaning 'it is cool,' after bringing peace to a region torn by internecine warfare." To be hip is to be awake and aware, to be pluperfect and invisibly graced, to possess secret knowledge, knowledge that makes the owner an initiate of a nameless sect whose members recognize one another by the use of certain words, the wearing of certain garments, the tilt of a hat, the roll of a cuff. The minute those words and styles pass into the public grasp it's time for hipsters to switch to other words, other styles. These days, with more squares than ever clamoring at the gates, assuming styles before hipsters have had a chance to try them on, it's very hard indeed to remain untouchably self-selected. That's why Pabst Blue Ribbon became the hip beer: It was unclaimed, a blue-collar vestige without a living constituency. The choice of hip shibboleths has become a process of elimination.

Leland has a multi-strand story to tell, with a great deal of heavy lifting, and he proceeds manfully, clocking a chapter at each of the major stops. The 19th century is represented on the one hand by the extraordinary foundation work of Thoreau, Melville, Whitman, and especially Emerson—a redoubtable tea leaf reader who seemingly forecast every American cultural trend of the future—and on the other by the rise of minstrelsy, which laid into the edifice an oddly shaped keystone labeled "irony." The 20th century is frenetic. You can connect the dots between New Orleans jazz and Greenwich Village bohemia and the Harlem Renaissance and the Paris exiles of the 1920s, and then hear the riff repeated in a new key after the Second World War by bebop and the Beats. But running sideways across the story are criminals, cartoons (was there ever a more perfect hipster than Bugs Bunny, at least before he became a shill?), film noir, the put-on, drugs. Jews represent a special case, understanding both sides of the racial dichotomy and playing both at once—like Rahsaan Roland Kirk and his two saxophones—while being correspondingly excluded by both. Women also represent a special case, hipper than hip unless they are relegated to reproduction and emptying bedpans. Further in the chronological narrative we have hippies (briefly) and punk and hip-hop and hackers and so on and did I mention drugs? There are so many intersecting story lines that the subject begs for a flowchart.

Hip: The History By John Leland Ecco, 405 pp., $26.95 Buy this book

Leland is a fluid writer, capable of unfurling a nice phrase, able to walk a very thin line in writing dispassionately about hip without coming off as an embalmer. Somewhere around chapter three ("Jazz, the Lost Generation, and the Harlem Renaissance"), though, I began to hear his spectral muttered curses as he came to the realization that his narrative would entail an endless assembly line of potted histories. He does manage to come up with some unexpected nuggets and apposite quotes, but if you have any previous acquaintance with his material you will wince as you are subjected yet again to anecdotes grown shiny with use. Starting about a third of the way in, your eyes will glaze over as the personnel of previous chapters is repeatedly brought back for curtain calls, so that the connections between hip model 1927 and hip model 1956 will not be lost on the sluggards in the back row. Of course, since the target audience for this project has a probable median age of 18, Leland is providing a public service in rehearsing the story of, say, the Lost Generation, since it needs to be differentiated from generations Beat, blank, and X. Teenage hipsters may once have been better versed in the works and days of their antecedents because they were so isolated, and information on current matters was so hard to come by, that in their desperation they were forced to resort to the library.

The other major hurdle faced by the author of such a book is that it is necessarily the product of any given present moment. Unless you declare an arbitrary stopping point and cast the whole business in the past tense, which will make you come off as an embalmer, you are faced with some tricky rhetorical footwork if you are to escape instant obsolescence. Leland looks around him at the spectrum of hipness at the time of writing and finds . . . trucker caps. He knows full well that trucker caps will have hit the boneyard long before publication day. How is he to suggest that hipness has a viable future? And like any writer pondering any continuum of history, he can view it, even with the best intentions, only through the inevitably myopic lenses of the moment. Leland looks back at a century and a half of hip for a sign, a previously overlooked curve that will connect the misty past with the confused present, a stone that the builders rejected that will prove to be the rock on which future hipness will thrive, and sees . . . advertising.

Thus, in his Mt. Rushmore of anticipatory hip, alongside the faces of Emerson, Thoreau, Melville, and Whitman, he carves the countenance of Volney Palmer, who "opened the first American ad agency in Philadelphia in 1841." Now, it's true that publicity has always been fundamentally important to artists struggling for recognition, and it has loomed even larger for hipsters, whose art is inseparably entwined with the packaging of their selves. (Oddly, Leland doesn't make much of Whitman's or Norman Mailer's self-advertisements.) Publicity was also a major component of modernism; in the 20th century all sorts of artists, even Communists, enjoyed trying to harness and replicate the iconic impact of ads. It's also true that advertising has continually leeched off vanguard art (advertising needs hip a lot more than hip needs advertising), and that selling the sizzle and allowing the steak to take care of itself—a precept dating back at least to the work of Edward Bernays, Freud's nephew, for the tobacco industry in the 1920s—is a recipe for merchandising hipness. But Leland has let his ear be bent by many "creatives" who are probably sincere in their belief that what they do is just like art, that it's abstract. Dig it, they're not selling cars—they're selling CDs by the hipsters whose tunes are used in the commercials! They're subverting the system from within! And the check is in the mail and I won't come in your mouth. The fact remains that, if you shill for enterprises that exist primarily to further enrich people who are already many times richer than you, you are a servant. And you can hold my coat.

Luc Sante has the same birthday as Miles Davis and Ralph Waldo Emerson.