I really like this description of where cool came from.  I don’t think I agree, but I like the way the guy puts it:

And what Frank Sinatra projected was: cool. And here is where the damage was done. Frank invented cool, and everyone followed Frank, and everything has been going to hell ever since.

In America, B.F., there was no cool. There was smart (as in the smart set), and urbane, and sophisticated, and fast and hip; but these things were not the same as cool. The pre-Frank hip guy, the model of aesthetic and moral superiority to which men aspired, is the American male of the 1930s and 1940s. He is Humphrey Bogart in The Big Sleep or Casablanca or Archie Goodwin in Rex Stout’s Nero Wolfe novels. He possesses an outward cynicism, but this is understood to be merely clothing; at his core, he is a square. He fights a lot, generally on the side of the underdog. He is willing to die for his beliefs, and his beliefs are, although he takes pains to hide it, old-fashioned. He believes in truth, justice, the American way, and love. He is on the side of the law, except when the law is crooked. He is not taken in by jingoism but he is himself a patriot; when there is a war, he goes to it. He is, after his fashion, a gentleman and, in a quite modern manner, a sexual egalitarian. He is forthright, contemptuous of dishonesty in all its forms, from posing to lying. He confronts his enemies openly and fairly, even if he might lose. He is honorable and virtuous, although he is properly suspicious of men who talk about honor and virtue. He may be world-weary, but he is not ironic.

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.

I found that at Instapundit.  It is from this.

I remember writing a pamphlet, way back when, entitled Why I Support The Contras, that included the observation that …:

… there seems to me to be something especially nasty about free, comfortable people choosing to decide questions of overwhelming historical and moral significance as if they were arguing about hemlines.

That’s in my penultimate paragraph, underneath my final subheading, “MORALITY AND STYLE”.  My point being that morality trumps style.

To put that in the language of cool and uncool, what I was getting at was that being an uncool anti-communist was good.  But being a cool pro-communist, or (almost as bad in my opinion) a cool anti-anti-communist, was evil.  And good and evil matter a hell of a lot more than cool and uncool.

I think that “cool” can be a virtue, related to the idea of “grace under fire”.  Cool, can, that is to say, overlap with virtue.  You can be cool while being – cool about being - good, or at least non-evil.

Cool and evil can go to hell, that being where it belongs.  But when Instapundit’s Ed Driscoll says, of that Michael Kelly quote, “spot on”, I disagree.  I don’t regard cool as being, in and of itself, evil.  It often is.  But it often isn’t.

But, what do I know?  The thing is, this is an argument about the meaning of a word, and the meaning of a word is often controversial.  To know what a word means, you have to know about how it is used.  Knowing how you think it should be used is not the same thing.  All I can say is that in my conversational circles, cool is not necessarily wicked.

I am quite prepared to believe that in Sinatra world, cool did indeed become very wicked indeed.