The Book Club

Sinatra’s Incomparable Love songs


Sinatra as a noir anti-hero, a singing Sam Spade! I love it; you’re spot-on. Look at that desolate In the Wee Small Hours album cover. Who can doubt that Sinatra, Humphrey Bogart’s biggest fan, had film noir in mind? Sinatra’s hardboiled persona was, as you say, a cartoon—and, sometimes, a trap. Unlike many Frankophiles, I’m not crazy about Sinatra’s saloon songs, which push the boozy romanticism a smidge too far.

But noir gave Sinatra a new way to sing the blues. And with help from Nelson Riddle, he used noir to move pop into groundbreaking conceptual territory. Listen to the eerie brass and woodwind fanfare in the opening measures of “Ill Wind.” That’s film noir soundtrack music. On In the Wee Small Hours and the other great Capitol albums, Sinatra and Riddle built and sustained a mood not unlike what John Huston and Bogie did in The Maltese Falcon. Pop had never been so cinematic, so self-consciously arty. We have Ol’ Blue Eyes to thank—to blame—for Sgt. Peppers’ Lonely Hearts Club Band and Dark Side of the Moon and Tales from Topographic Oceans and every other wild-eyed concept album that art-rockers disgorged in the decades following.


Noir wasn’t the only way that Sinatra caught the spirit of his times. In the first couple of decades of the 20th century, pop songs were like newspaper dispatches, taking in the whole pageant of Progressive Era life: politics, war, dance crazes, sports, inventions, the melting pot. But in Sinatra’s prime—the so-called golden age of popular song—the hit parade narrowed to a nearly monomaniacal focus on romance. The tunesmith’s task, according to the Tin Pan Alley adage, was to “say ‘I love you’ in 32 bars.” As Ira Gershwin put it in a famous parody: “Blah, blah, blah, blah love … Tra la la la, tra la la la cottage for two.”

Of course, the best songs transcended blah, blah, blah—and pop song love could contain multitudes. “The implicit and compelling argument,” Kaplan writes, “was that love was the ultimate human subject, and could therefore encompass absolutely any idea or shade of emotion: euphoria, sorrow, lust, hate, ambivalence, cynicism, naughty fun, surprise, surrender.” Kaplan’s larger point, I think, is that Sinatra’s interpretive genius was inseparable from his romantic voraciousness. Who better to take on the “ultimate human subject” than the man who’d looked at it from both sides, from every angle? Ava Gardner, meanwhile, taught Sinatra that love is an insoluble puzzle, a case that no film noir gumshoe could crack. “What is this thing called love?” Sinatra memorably sang. “Who can solve its mystery? Why should it make a fool of me?”


Cole Porter wrote those lines, of course. Sinatra was the beneficiary of some of the finest songwriting in pop history. But as Kaplan shows, he was also a connoisseur, attuned to “the differences between poor and fair and good and great songs.” A common denominator of those songs was, for lack of a better term, an adult outlook. In his personal life, Sinatra was impetuous and immature; in his art, he was a grownup, a dedicated explorer of adult relationships and emotions. It was a lifelong project: In his later years, he took on the topic of aging with unusual forthrightness, and the result was one of pop’s greatest lion-in-winter acts.

As Sinatra’s vocal powers waned, he compensated with bluster: cf. “My Way,” perhaps his most famous record, definitely his worst. It was embarrassing schlock, but it was also Frank being Frank. Of course he’d go down swinging.

I wish Kaplan had had a more ruthless editor and had gotten around to Sinatra’s second and third and fourth acts. I’m not sure I believe in multivolume biographies; 800 pages should be sufficient to cover even a life as plus-size as Sinatra’s. But Kaplan’s hooked me in: I’ll be at the bookstore to get my copy when Volume 2 comes out. If bookstores still exist.

Until then, Ann,

I’ll be seeing you,

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