Norman Mailer set the agenda in the 1950s when he wrote that society was divided into two types of people: the hip (“rebels”) and the square (“conformists”). Cool (or hip, alternative, or edgy) here becomes the universal stance of individualism, with the hipster as the resolute nonconformist refusing to bend before the homogenizing forces of mass society. In other words, the notion of cool only ever made sense as a foil to something else, that is, a culture dominated by mass media such as national television stations, wide-circulation magazines and newspapers, and commercial record labels. The hipster makes a political statement by rejecting mass society and its conformist agenda.

Like George Bush’s infamous declaration that “you are either with us or you are with the terrorists,” this Manichean characterization of cool gives its a great deal of power as a form of political and social criticism, by allowing us to situate everyone on one side or the other of a great divide. Either you are over here with hipsters, or you are over there with the conformist (and latently fascist) squares. But the truth is, cool is not political, and it never was. The reason why anyone ever thought that being cool did have political consequences was because of the tremendous amount of friction in the transmission of culture. It took a long time for subcultural trends in fashion or music or speech to move from the streets of London or New York City to the suburban basements of Omaha or Ottawa, and the phenomenon we call “cool” was just a consequence of that friction. Cool people were just those who had early access to new cultural trends, which gave them a great deal of status. Not only did it allow them to portray themselves as political radicals, it also allowed them to treat those who were not “in the know” as the mindless dupes of mass society.

- Andrew Potter, The Authenticity Hoax