Coolness started with jazz musicians, and still has something of the spirit of the night, of escape from everyday reality, of unconditioned freedom, of improvisation without a goal. It’s the liberal equivalent of the divine grace that bloweth where it listeth and none can define.
It has something in common with sanctity. The cool are in the world but not of it. They possess a certain disengagement, so that they are independent of their surroundings and not easily flustered or excited. They’re not conventional, and recognize immediately whatever they’re presented with. That gives them a sort of perfect pitch in matters of perception, expression, and practical decision.
Of course, coolness is also very different from sanctity. Sanctity is about eternity, coolness about today. It has religious aspirations, but its hedonism and individualism means it goes nowhere. The lives of the saints have enduring interest because they point to something beyond themselves, the lives of the hipsters don’t. – James Kalb
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