From The New Yorker:
Having come out of the closet, or the casino, not long ago, as an unqualified Frank Sinatra idolater, I approached the second volume of James Kaplan’s biography of the singer (“Sinatra: The Chairman”) with what our critical mothers and fathers would have called immense trepidation, since the book would have to deal not just with the great man’s best records but with his messy entanglement with the mob and his sad, stultified later years. (I saw him perform once, toward the very end, at Madison Square Garden, and it was like seeing the dead El Cid mounted on his horse to lead the Spanish Army: noble but undeniably stiff.)
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The ugly, scuttlebutt version of Sinatra is as a bad guy with a big voice. Kaplan shows that the bad-guy stuff was, in truth, pretty bad, about as bad as one had imagined and a lot worse than one had hoped. He did hang out with and cultivate mobsters, real killers, though more in a semi-hostile, semi-affectionate fraternal manner than with the pitiful, feudal devotion pictured in “The Godfather.” (There seems to be no truth in the rumors that the mob bullied Harry Cohn into casting Sinatra in “From Here To Eternity,” not least because Cohn was plenty mobbed-up himself.)
Worse, Sinatra beat people up, or had others beat them up for him, often in shameful acts of bullying—picking on casino employees or less successful, dependent entertainers. (This happened to Shecky Greene, who emerges in the biography as a far more interesting and volatile man than one could have ever imagined, and, weirdly, to Jackie Mason, who had shots fired at him, apparently for dissing the Chairman.) Kaplan even offers veiled, worrying hints that Sinatra might have been implicated in an actual murder. (A man with whom he had an altercation was killed in a mysterious traffic accident a few weeks later.) These instances were sporadic and counterbalanced by his many acts of charity, some impulsive, and some systematic—touring for the benefit of children’s hospitals and the like.
Sinatra’s character flaw isn’t hard to name. He lived in daily fear of humiliation, and in its (often imagined) presence his temper tipped over in an instant. This was followed, usually, by remorse, once he had sobered up and stopped seeing red. But, in the interim, real damage was done to real people: he threw a telephone at a businessman once at the Beverly Hills Hotel, fracturing his skull and very nearly killing him. The other cause of his rage may be oddly taboo to tell. Sinatra was a bad, mean drunk, and, since he was often drunk, he was often bad and mean. (John Lennon was a bad, mean drunk, too, and when he got loose long enough to show it the author of “Imagine” and “Julia” could do similarly violent things.) Despite everything we ought to have learned, we still make a ballad out of alcohol. It was Jack on the rocks, not crack from a bag, and so we somehow think that it’s not so bad. The other sad truth Kaplan illustrates is that demons rage in the rich and famous as much as they do in the poor and unknown—and maybe rage still more, since, having defeated the usual demons of worldly failure that haunt the rest of us, the famous are left alone with the remaining, inexpungible ones, grinning up evilly at them from inside.
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Sinatra, he shows, had an astonishing musical intelligence, of a subtlety and soulfulness still unequalled. He was a master of understatement and narrative so complete that he could still spellbind audiences after his voice had gone, and he was even more of a legend among other musicians than among his fans. Nor is Kaplan simply an idolater. He sees how genius sits in a fortunate network, offering character sketches of Sinatra’s arrangers, who were as essential to Sinatra’s art as George Martin’s production was to the Beatles. They’re captured as more than names: the saturnine Nelson Riddle, the last-minute genius Billy May, and the old-fashioned Gordon Jenkins, not to mention supporters as gifted and forgotten as Milt Bernhart, who played the indelible trombone solo on Riddle’s transformed version of Cole Porter’s “I’ve Got You Under My Skin.”
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And then, one of the things you learn ever more certainly as you grow older is that all art is made in the image of the artist. It can often be articulated as an opposite, with all the low spots in life thrust forward in art, as with Sinatra. But it is some sort of picture. It isn’t supposed to be so; high-minded people are supposed to pull life and art apart, trust the tale not the teller, and all that. But if an abstract artist makes pictures only of white, there is a white moment, or knight, somewhere there in her past, bugging her still. Sinatra’s painfully bipolar nature is exactly the pattern of his best music, with “swinging” records continually succeeded by sad ones, again and again.
Link to the rest at The New Yorker