Lots of slang phrases change their meaning over time. It is far less likely, however, for such phrases to acquire an almost reverse meaning.
Among the rare exceptions are hip and hipster.
For example, an online dictionary defines hip as
This could hardly be further from the use of the term in the 1940s and 1950s when its early use was at a peak.
In this case, the shift is not merely a historical curiosity but revealing of changes in the culture of younger Americans in the two periods.
For example, one definition of the earlier meaning noted:
In other words, a culture of alienation instead of one of fashion and style.
But a check of Google hits finds the use of the word hipster with the word alienation to have occurred 114,000 times over the past year while the use of hipster with style occurred 35 million times.
One way of describing this is that despite a near-depression, being part of the first generation of Americans that cant see the future getting better, and having just about every great institution collapsing around them, the young still think of hipness as a matter of fashion rather than of rebellion or alienation.
This is not their fault. The explosion of state and corporate propaganda (aka public relations) with its insidious manipulation of personal values has greatly weakened average Americans ability to make up their own minds.
Nonetheless, the phenomenon serves as a clue as to why in these terrible times there is so little rebellion in America compared, say, to the Middle East. Or even Europe.
Wikpedia has a couple of instructive quotes on the topic:
In his book Jazz, Frank Tirro defines the 1940s hipster: To the hipster, Bird [Charlie Parker]was a living justification of their philosophy. The hipster is an underground man. He is to the Second World War what the dadaist was to the first. He is amoral, anarchistic, gentle, and overcivilized to the point of decadence. He is always ten steps ahead of the game because of his awareness. . . He knows the hypocrisy of bureaucracy, the hatred implicit in religions - so what values are left for him? - except to go through life avoiding pain, keep his emotions in check, and after that, be cool, and look for kicks. He is looKing for something that transcends all this bullshit and finds it in jazz.
Marty Jezer, in his book The Dark Ages: Life In The U.S. 19451960 defines the 1940s hipster: The hipster world that Kerouac and Ginsberg drifted in and out of from the mid-forties to the early-fifties was an amorphous movement without ideology, more a pose than an attitude; a way of being without attempting to explain why. Hipsters themselves were not about to supply explanations. Their language, limited as it was, was sufficiently obscure to defy translation into everyday speech. Their rejection of the commonplace was so complete that they could barely acknowledge reality. The measure of their withdrawal was their distrust of language. . . There was neither a future nor a past, only a present that existed on the existential wings of sound. A Charlie Parker bebop solo - that was the truth. The hipster's world view was not divided between "free world" and "Communist bloc", and this too set it apart from the then-current orthodoxy. Hipster dualism, instead, transcended geopolitical lines in favor of levels of consciousness. The division was hip and square. . . In the wigged-out, flipped-out, zonked-out hipster world, Roosevelt, Churchill, Stalin, Truman, McCarthy and Eisenhower shared one thing in common: they were squares. . .
I touched on a related term in my book, Why Bother?:
||| In beat culture, jazz, and the civil rights movement there had been a stunning critique of, and rebellion against, the adjacent and the imposed.
Steven Watson credits the term beat to circus and carnival argot, later absorbed by the drug culture. "Beat" meant robbed or cheated as in a "beat deal." Herbert Huncke, who picked up the word from show business friends and spread it to the likes of William Burroughs, Allen Ginsberg, and Jack Kerouac, would say later that he never meant it to be elevating: "I meant beaten. The world against me."
Gregory Corso defined it this way, "By avoiding society you become separate from society and being separate from society is being beat." Keruoac, on the other hand, thought it involved "mystical detachment and relaxation of social and sexual tensions."
Inherent in all this was not only rebellion but a journey. "We were leaving confusion and nonsense behind and performing our one and noble function of the time, move," wrote Kerouac in On the Road.
It is instructive during a time in which even alienated progressives outfit themselves with mission and vision statements and speak the bureaucratic argot of their oppressors to revisit that under-missioned, under-visioned culture of what Norman Mailer called the "psychic outlaw" and "the rebel cell in our social body." What Ned Plotsky termed, "the draft dodgers of commercial civilization."
Unlike today's activists they lacked a plan; unlike those of the 60s they lacked anything to plan for; what substituted for utopia and organization was the freedom to think, to speak, to move at will in a culture that thought it had adequately taken care of all such matters. Although the beats are frequently parodied for their dress, sartorial nonconformity was actually more a matter of indifference rather than, as in the case of some of the more recently alienated, conscious style. They even wore ties from time to time. Yet so fixed was the stereotype that the caption of a 1950s AP photograph of habitués in front of Washington's Coffee 'n' Confusion Café described it as a place for bearded beatniks when not one person in the picture had a beard. Rather they were a bunch of young white guys with white shirts and short haircuts. Cool resided in a nonchalant, negligent non-conformity rather than in a considered counter style and counter symbolism..
To a far great degree than rebellions that followed, the beat culture created its message by being rather than doing, rejection rather than confrontation, sensibility rather than strategy, journeys instead of movements, words and music instead of acts, and informal communities rather than formal institutions.
For the both the contemporaneous civil rights movement and the 1960s rebellion that followed, such a revolt by attitude seemed far from enough. Yet these full-fledged uprisings could not have occurred without years of anger and hope being expressed in more individualistic and less disciplined ways, ways that may seem ineffective in retrospect yet served as absolutely necessary scaffolding with which to build a powerful movement.
With the end of the Vietnam War, America soon found itself without a counterculture or - with a few exceptions - even a visible resistance by societal draft dodgers. The young -- in the best of times the most reliable harbinger of hope; in the worst of times, the most dismal sign of futility -- increasingly faced a culture that seemed impermeable and immutable. The establishment presented a stolid, unyielding, unthinking, unimaginative wall of bland certainty. It looked upon pain, aspiration and hope with indifference, and played out false and time-doomed fantasies to the mindless applause of its constituency.
The unalterable armies of the law became far more powerful and less forgiving. The price of careless or reckless rebellion became higher. Bohemia was bought and franchised. Even progressive organizations required a strategic plan, budget, and press kit before heading to the barricades. A school district in Maryland told its teachers not to include creativity or initiative in a student's grades because they were too hard to define. Hipness became a multinational industry and no one apparently thought twice about putting a headline on the cover of a magazine "for men of color" that declared "The Rebirth of Cool," exemplified by 50 pages of fashions by mostly white designers. ||||
Today the closest thing to the former definition of hip is punk culture. Perhaps a little too manic in its music and aggressive in its fashion statement to please a Miles Davis or Jack Kerouac, but miles closer to that earlier definition of hip.
What difference does it make? Only this: America will most likely gain a new life when the young break dramatically away from the system that has left them in this miserable state. A fashionable rebellion is an oxymoron. And when the young in large numbers recognize this, they will also probably find themselves moving towards an earlier definition of hip, such as that offered by proto-rapper Harry Gibson in 1947: