Tremendous passage from the late Michael Kelly, found via Cold Fury:

Sinatra, as every obit observed, was the first true modern pop idol, inspiring in the 1940s the sort of mass adulation that was to become a familiar phenomenon in the '50s and '60s. One man, strolling onto the set at precisely the right moment in the youth of the Entertainment Age, made himself the prototype of the age's essential figure: the iconic celebrity. The iconic celebrity is the result of the central confusion of the age, which is that people possessed of creative or artistic gifts are somehow teachers-role models-in matters of personal conduct. The iconic celebrity is idolized-and obsessively studied and massively imitated-not merely for the creation of art but for the creation of public self, for the confection of affect and biography that the artist projects onto the national screen.

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.

One of the observations that Diana West made in The Death of the Grown-Up is how much of the heavy lifting in the birth of modern culture--with all its pluses and minuses--occurred in the 1950s, though the 1960s gets all the credit.

But while Sinatra was indeed a harbinger of things to come, he was also very much a man of his times. In Gay Talese's epochal 1966 "Frank Sinatra Has A Cold" article for Esquire, you can actually see the cool style of Sinatra’s highpoint ebb into the sunset, and the aesthetic of the late sixties being born, when Sinatra encounters legendarily cranky sci-fi writer Harlan Ellison.

And as Mark Steyn wrote recently, by the following decade dispatches between the two cultures--the post-war showbiz culture and the anti-war culture of mud--were even chillier:

One reason why the Oscar shows of the early Seventies are such a hoot compared to the butt-numbing snoozeroos of today is the tension and sniping between the John Wayne/Bob Hope/Frank Sinatra set and the hipster crowd reading out telegrams from the Viet Cong. Back then, being anti-war meant taking a side. In today’s Hollywood, being anti-war is the only side.

Which means, through the paradigm of The Manchurian Candidate and even programmers like Von Ryan's Express, plus his support of JFK and RWR, we can look back at Sinatra as a remarkably patriotic, all-American guy, in spite of himself, his myriad excesses, and nihilistic cool.

Maybe it was simply that while Sinatra was indeed cool, he never succumbed to its successor pose: irony. Which, in retrospect, may have saved him from himself, unlike those who followed in his wake.

Update: Welcome Libertas and Jules Crittenden readers!