According to 'Hip: The History' author John Leland
Kind of Blue, Miles Davis (1959). Still booty after all these years.
The Velvet Underground & Nico (1967). As Brian Eno said, no one bought it when it came out, but everyone who did started a band.
Bringing it All Back Home, Bob Dylan (1965). Nearly 40 years later, Johnny’s still in the basement, mixing up the medicine, only now he’s ogling Victoria’s Secret models in the bargain.
There’s a Riot Goin' On, Sly & the Family Stone (1971). The heady, multi-culti throwdown that invented Prince.
Horses, Patti Smith (1975). If Mick, Keith, Dylan and Burroughs were combined in one skinny, bad chick from New Jersey.
The Shape of Jazz to Come, Ornette Coleman Quartet (1959). Cerebral and constantly falling apart, like most hipsters we know.
Slanted and Enchanted, Pavement (1992). Hip enough to keep its secrets and share them too.
Hipsters, Flipsters and Finger-Poppin' Daddies, Knock Me Your Lobes, Lord Buckley (1955). Not the original rapper, but perhaps the funniest. The title, of course, is Shakespeare.
Paid in Full, Eric B. & Rakim (1987). Still the chillest in deadpan hip-hop, without gunplay or misogyny. Rakim holds the microphone like a grudge.
Hoodoo Man Blues, Junior Wells (1953). A lethal assault on the backbone, Chicago-style.
Top 10 Hip Books
Leaves of Grass, Walt Whitman. Wise, erotic, self-indulgent, universalist: the big daddy that started it all.
On the Road, Jack Kerouac (1957). The great novel of hipster friendship.
Invisible Man, Ralph Ellison (1952). A pitiless search for the self, best accompanied by Trading Twelves, Ellison’s letters to and from Albert Murray.
The Long Goodbye, Raymond Chandler (1953). The hardboiled detective novel at its most poetic and ambitious, but with plenty of foul play for the kids.
Mumbo Jumbo, Ishmael Reed (1972). A sly, sideways, subversive journey through the dirty laundry of Western Civ.
The Confidence-Man, Herman Melville (1857). The schemer or trickster as American icon, inventing himself as his greatest gift to his patsies.
Naked Lunch, William S. Burroughs (1959). The first megamix novel, cut up and reassembled. Sorry, Mr. Diddy: Burroughs and Brion Gyson invented the remix.
The Adventures of Huckleberry Finn, Mark Twain (1885). On the Road, only on the river. Hemmingway called it the fount from which all American lit flowed, Leslie Fiedler called it a homoerotic minstrel show, and Shelley Fisher Fishkin asked, Was Huck Black?
Neuromancer, William Gibson (1984). Future sex, drugs, dub, female assassins and boys playing with computers. And written by a Canadian to boot!
Jesus' Son, Denis Johnson (1992). Junkie slackness, at its funniest and most acute. Notable for the addict Kid Williams, who wasted his entire life, giving his brethren forgiveness to waste a little more of theirs.
What do Miles Davis, Ralph Waldo Emerson and Bugs Bunny have in common? They're all hip, says John Leland, the author of a new history of that coveted but elusive quality.
Top 10 Hip Films
(With Dennis Hopper)
Rebel Without a Cause (1955)
The Trip (1967)
Easy Rider (1969)
Out of the Blue (1980)
River’s Edge (1986)
Blue Velvet (1986)
Straight to Hell (1987)
True Romance (1993)
Grand Theft Auto: Vice City (video game) (2002)
"We wouldn't think of Emerson as the classic hipster," Leland tells NPR's Renee Montagne. "He's not Jack Kerouac a century removed. But Emerson and his emphasis on the individual rather than society... and on self-reliance... those are all the building blocks of hip."
In, Hip: The History, Leland tells the story of America's tense relationship between outsiders and insiders, most profoundly between white Americans and Africans Americans.
Modern hipsters owe a lot to African-American folk tales, Leland says. The hero was usually a trickster who was smarter than his oppressors. That story continued, from Brer Rabbit to Huck Finn to the superstar of folk hipsters -- Bugs Bunny.
"I think he taught so many Americans how to be hip..." Leland says of the Looney Tunes legend who constantly outwitted Elmer Fudd. "You're smarter than the person who's tormenting you even though he's got more power than you. He's got the big rifle, but you are living by your wits and your own creativity. What did Bugs do? He switches genders, he sasses authority. Bugs does everything that we would tell our kids not to do."
The following is an excerpt from Hip: The History.
Book Excerpt: What is Hip? Superficial Reflections on America
The Oakland soul group Tower of Power asked the question in a 1973 song called "What Is Hip?" The band had a reputation as wordsmiths, inventing terms like honkypox, for listeners who could not get on the good foot. But on the Hip Question, they found themselves on slippery terrain, as poets before them trying to define soul or swing or love. The language curled back on itself:
Hipness is—What it is!
And sometimes hipness is
What it ain't!
Swaddled in nasty horns and a backbeat, this was a coy put-on, staged for the benefit of the honkypox. Everybody knows what hip is.
Or at least, everyone can name it when they see it. For something that is by definition subjective, hip is astoundingly uniform across the population. It is the beatitude of Thelonious Monk at the piano, or the stoic brutality of Lou Reed and the Velvet Underground, performing songs of drugs and sadomasochism as a projector flashed Andy Warhol's films on their black turtlenecks. It is the flow of Jack Kerouac's "bop prosody" or Lenny Bruce's jazzed-out satire, or the rat-a-tat tattoo of James Ellroy's elevated pulp lit. Walt Whitman was hip; Lord Buckley was hip; Karen O of the Yeah Yeah Yeahs is too hip for her own good.Hip is the way Miles Davis talked, dressed, played or just stood—and the way Bob Dylan, after his own style, followed in kind (though both men strayed into injudicious leather in the 1980s). The streets of Williamsburg in Brooklyn or Silver Lake in Los Angeles comprise a theme park in the key of hip. Its gaze is the knowing, raised eyebrow of Dawn Powell or Kim Gordon, bassist in the downtown band Sonic Youth—skeptical but not unkind.
Clarence Major, in his study Juba to Jive: A Dictionary of African-American Slang, traces the origins of hip to the Wolof verb hepi ("to see") or hipi ("to open one's eyes"), and dates its usage in America to the 1700s. So from the linguistic start, hip is a term of enlightenment, cultivated by slaves from the West African nations of Senegal and coastal Gambia. The slaves also brought the Wolof dega ("to understand"), source of the colloquial dig, and jev ("to disparage or talk falsely"), the root of jive. Hip begins, then, as a subversive intelligence that outsiders developed under the eye of insiders. It was one of the tools Africans developed to negotiate an alien landscape, and one of the legacies they contributed to it. The feedback loop of white imitation, co-optation and homage began immediately.
From these origins, hip tells a story of black and white America, and the dance of conflict and curiosity that binds it. In a history often defined by racial clash, hip offers an alternative account of centuries of contact and emulation, of back-and-forth. This line of mutual influence, which we seldom talk about, is not a decorative fillip on the national identity but one of the central, life-giving arteries. Though the line often disappears in daily life—through segregation, job discrimination and the racial split in any school cafeteria—it surfaces in popular culture, where Americans collect their fantasies of what they might be. The center of American culture runs through Mark Twain and Louis Armstrong, and it is impossible to imagine either's work without both African and European roots. Born in radically different circumstances and separated by history, they have as much in common with each other as with their peers from what either might call the ancestral homeland. Both are classicists and bluesmen, masters of language, breakers of the rules that would hold them apart. What they have in common is hip.
For better and worse, hip represents a dream of America. At its best, it imagines the racial fluidity of pop culture as the real America, the one we are yearning to become. As William Burroughs said, revolution in America begins in books and music, then waits for political operatives to "implement change after the fact." At its worst, hip glosses over real division and inequity, pretending that the right argot and record collection can outweigh the burden of racial history. White hipsters often use their interest in black culture to claim moral high ground, while giving nothing back. When Quentin Tarantino tosses around the word nigger, he is claiming hipster intimacy while giving callous offense. Really that high ground lies elsewhere. Hip can be a self-serving release from white liberal guilt, offering cultural reparations in place of the more substantive kind. This is white supremacy posing as appreciation. Neither of these verdicts on hip is strong enough to cancel the other out. Hip serves both functions: it is an ennobling force that covers for ignominy. Steeped in this paradox, it tells a story of synthesis in the context of separation. Its métier is ambiguity and contradiction. Its bad is often good.
Only a small fraction of the population at any time lives in full commitment to hip; for most of us, work, school, family, rehab or the alarm clock gets in the way. Yet we all participate in its romance. Its Q rating is to die for. Hip permeates mainstream daily life at the level of language, music, literature, sex, fashion, ego and commerce. During the 1992 presidential campaign, Bill Clinton made hip a campaign pitch, working sunglasses and sax on The Arsenio Hall Show; for his troubles, both Toni Morrison and Chris Rock anointed him America's first black president. (A decade later Al Sharpton refined this title, quipping, "There is a difference in being off-white and being black.")
If hip is a form of rebellion—or at least a show of rebellion—it should want something. Its desires are America's other appetite, not for wealth but for autonomy. It is a common folk's grab at rich folks' freedom—the purest form of which is freedom from the demands of money. It is an equalizer, available to outsiders as to insiders. Anyone can be hip, even if everyone can't. In a nation that does not believe in delayed gratification, hip is an instant payoff. You may need years of sacrifice to get to heaven or build a retirement fund, but hip yields its fruit on contact. It is always new but never going anywhere special—a present tense reclaimed from the demands of past and future.
Like other manifestations of the blues, hip keeps its meaning limber. John Lennon, pursuing his domestic bliss in New York City, saw hip as a drag. "Nowadays it's hip not to be married," he said in 1980. "I'm not interested in being hip." For the surreal comic Richard "Lord" Buckley, on the other hand, the word "hip" signified a rain of good fortune. In his rewrite of Mark Antony's funeral oration from Julius Caesar, he unlocked Shakespeare's inner hipster, riffing, "Yea, the looty was booty and hipped the treasury well." For Lennon, hip was a prison; for His Lordship, it was whatever was needed, as long as you didn't have to work for it. But even Lennon would have acknowledged that the looty was booty.
The booty, in turn, has bounty. Hip sells cars, soda, snowboards, skateboards, computers, type fonts, booze, drugs, cigarettes, CDs, shoes, shades and home accessories. As Lord Buckley suggested, it serves the treasury well. By bringing constant change and obsolescence, it creates ever-new needs to buy. Though it grabs ideas from the bottom of the economic ladder, hip lives in luxury. Poor societies worry about growing enough corn; rich societies can worry about being corny. Hip shapes how we drive, whom we admire, whose warmth we yearn for in the night. Its scent transforms neighborhoods from forbidding to unaffordable. The fashion designers Imitation of Christ built a thriving label by murmuring a mantra of hip over thrift store clothes, then selling them for hundreds of dollars. Hip brings the intelligence of troublemakers and outsiders into the loop, saving the mainstream from its own limits. What's in Williamsburg today will be in the mall tomorrow; today's Vice magazine or Lucha Libre Mexican wrestling is tomorrow's Good Housekeeping or SmackDown. Like the advertising world that grew up alongside it, hip creates value through image and style. In its emphasis on being watched, it anticipated the modern mediascape, which values people not for what they produce or possess but for their salience as images. For all its professed disregard for wealth, hip would not have thrived unless it was turning a profit.
Hip is a social relation. You cannot be hip in the way you might be tall, handsome, gawky, nearsighted or Russian. Like camp, its unruly nephew, it requires an audience. Even at its most subterranean, it exists in public view, its parameters defined by the people watching it. You decide what is hip and what is not. Hip requires a transaction, an acknowledgment. If a tree falls in the forest and no one notices its fundamental dopeness, it is not hip.