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While some would argue that it was Marlon Brando who created the notion of “cool” in the 1950s, back in the 1990s, the late Michael Kelly wrote that in his opinion it was Frank Sinatra who defined the term in that mid-century decade — and it was very much a mixed blessing, as Kelly wrote:
The new cool man that Sinatra defined was a very different creature. Cool said the old values were for suckers. Cool was looking out for number one always. Cool didn’t get mad; it got even. Cool didn’t go to war: Saps went to war, and anyway, cool had no beliefs it was willing to die for. Cool never, ever, got in a fight it might lose; cool had friends who could take care of that sort of thing. Cool was a cad and boastful about it; in cool’s philosophy, the lady was always a tramp, and to be treated accordingly. Cool was not on the side of the law; cool made its own laws. Cool was not knowing but still essentially idealistic; cool was nihilistic. Cool was not virtuous; it reveled in vice. Before cool, being good was still hip; after cool, only being bad was.