This piece originally appeared in 2002 in slightly different form in the publication formerly known as Salon.
You could forget that the guy ever had a good day. After Billie Holiday, nobody in American music has ever done more to slake our taste for romantic masochism than Frank Sinatra. The album covers told part of the story.
In the Wee Small Hours, with its painting of Sinatra under a street light in the blue-green gloom of a deserted 3AM city street. Or Frank Sinatra Sings for Only the Lonely, where a garish painting depicts him as a tear-stained Pierrot.
Or No One Cares, where he sits staring into his drink at a bar while all around him couples are having a good time.
The music told the rest of the tale. Taking off from the soft, dreamy voice that the young Sinatra used on his 40s Columbia recordings, where he was surrounded by Axel Stordahl’s sensitive arrangements, Sinatra’s Capitol work, from 1953 to 1962 (when he left for his own label, Reprise), presented that lovelorn youth transformed into a wounded, love-struck man, deeper-voiced, older and thus with more to lose.
At their best--the songs “In the Wee Small Hours,” his mournful and deeply strange version of Bunny Berigan’s “I Can't Get Started” (in which Berigan’s light, easy-come-easy-go loser’s panache was traded for a devastated gravity), and most of all in “Cottage for Sale,” a recording so painful that there are times I can scarcely bring myself to listen to it—Sinatra’s performances went beyond luxuriant self-pity and approached luxuriant tragedy.
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