I'M THINKING OF MAKING ON THE ROAD A vast story of those I know," Jack Kerouac confided to his journals, "as well as a study of rain and rivers." Rain and rivers--why not? For his hyperkinetic, endearing, exasperating 1957 novel, Kerouac tried to admit whole worlds. An account of a few pinwheeling characters in perpetual cross-country motion, it had room to spare for rivers, landscapes, starry skies, Benzedrine addicts, endless marathons of driving and lots of fast-talking madmen. "Because the only people for me are the mad ones," Kerouac's narrator, Sal Paradise, tells us. "The ones who are mad to live, mad to talk, mad to be saved."
You might assume that Kerouac was as wild as Dean Moriarty, the human jackhammer at the book's center, who was based on Kerouac's soul mate, Neal Cassady. On the Road made Kerouac the spokesman for the Beat Generation, an icon of hip. But that's not the man you meet in Windblown World: The Journals of Jack Kerouac 1947-1954 (Viking; 371 pages), a poignant selection of Kerouac's diaries edited by the historian Douglas Brinkley. The journals begin with Kerouac at 25, anguishing over his first novel, The Town and the City ("Why doesn't God appear to me to tell me I'm on the right track?"). They follow him through travels he made for On the Road, "hurt and haunted by hurt." The quintessential hipster turns out to be a guy whose hallmarks are tenderness, bewilderment and yearning.
Should that be surprising? Hip was never just the present-day array of marketable postures, most announcing an ironclad cool. But what is it exactly? For some interesting answers, turn to John Leland's Hip: The History (Ecco; 405 pages), a book that examines how an underground language of American slaves became the lingua francafor cooler-than-thou folk everywhere, in the process evolving from hard-earned mentality to merest merchandise option.
Leland has a weakness for phrasemaking and surplus rhetoric but a real gift for connecting centuries-old developments in American life to the endlessly evolving postures we call "hip." In the sensual ecstasies of Walt Whitman and the individualism of Ralph Waldo Emerson he finds hip's literary underpinnings. He maps the spiritual connections between the bleak machismo of West Coast--detective fiction and the desperado postures of L.A. gangsta rap. He points out the lines that connect hip-hop, with its audience of white suburban boys, to 19th century minstrel shows, in which whites in blackface strutted racial clichés before applauding white ticket buyers.