As it develops in jazz circles, Cool expresses an attitude of easy defiance; of not caring what other people think of you; of thumbing your nose at the world and casting your fate to the wind and damning the consequences, whether relating to the drug laws or anything else. Cool is being able to be cool even after losing your cool, about being so cool that you don’t even have to be cool…

Elements of all of these ideas coalesce powerfully in the jazz world of the 1930s and 1940s, as swing and later bebop provide jazz with a dangerous and seductive outlaw allure. Bebop is fundamentally the music of rebels and underdogs, played in dark smoky clubs by musicians in dark shades who turn their backs on their audiences as they turn away from society, erecting a wall of ironic detachment behind which they can make up their own rules and use narcotics as their drug of choice, all of which invites retribution from police. Cool is Charlie “Bird” Parker, the tragic genius and living personification of hipsterism. 

The hipster "is to the Second World War what the Dadaist was to the first," writes jazz impresario Robert Reisner. "He is amoral, anarchistic, gentle, and over-civilized to the point of decadence…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 this bullshit and finds it in jazz."

Ultimately, Cool is Miles Davis, who records a series of sides in 1948 and calls it The Birth of the Cool. Miles is an angry young man, and as Jazz Cool languishes mostly underground in a subculture of hipsters throughout the forties and well into the fifties, nothing expresses it more than the expression of seething world-weary disdain that Miles so often uses--“So what?” In 1956, the expression becomes the name of a song on his album masterpiece, Kind Of Blue.

The importance of Jazz Cool is hard to overstate.  It becomes a central sensibility in the literature of the Beat Generation, which finds its way to a mass middle class white audience during the 1950s. One would only have to ask someone like Clint Eastwood, a jazz-besotted teenager at Oakland Technical High in the late 1940s, about the Cool of Miles Davis to gauge how important an influence Davis was on Eastwood’s own outlook and development and place in this story...

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