In his book, Thing Worth Fighting For, the late Michael Kelly makes some interesting observations:
Frank Sinatra: The First Hippie
... No, if you want to finger any one person, place, or thing for what went wrong with America, you need look no further than that accidental one man validation of the great-man theory of history, Francis Albert Sinatra, 1915-98. Yes-The Voice, the Chairman of the Board, Old Blue Eyes, the leader of the (rat) pack, the swinger in chief-he's the culprit. It's all Frankie's fault.And all along I had thought that it was the deep thinking hippies of the 60's that introduced the scorn for all things bourgeois. Far out, Maaan!
American popular culture-which is more and more the only culture America has, which is more and more the only culture everyone else in the world has (we live, as the gormless Al Gore keeps chirpily and horrifyingly reminding us, in a global village)-may be divided into two absolutely distinct ages: Before Frank and After Frank...
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.
Quite a legacy. On the other hand, he sure could sing.1
(H.T. Ed Driscoll.)