The Book Club

What Sinatra Really Needed From the Mob

"Frank: The Voice."


I stepped into a bookstore yesterday, and, sure enough, there was Frank: The Voice jostling for display table space with Keith Richards’ Life. Decades later, the culture war between the baby boomers and their parents still has juice! You’re right, Ann, that Sinatra didn’t care much for rock ’n’ roll. “It is sung, played and written, for the most part, by cretinous goons,” he said in 1957. “And by means of its almost imbecilic reiteration, and sly, lewd and in plain fact, dirty lyrics … it manages to be the martial music of every side-burned delinquent on the face of the earth.”

That was the party line for Sinatra’s generation, but he was too smart, too musically astute, to stick to it. By the time the late-’60s rolled around, he had made peace with the tunes, if not the facial hair; he loved a good marriage of words and melody too much to deny Stevie Wonder and the Beatles. Sinatra’s experiments with the rock-era songbook were sometimes awkward—”The PTA, Mrs. Robinson, won’t OK the way you do your thing/ Ding, ding, ding“—but they were heartfelt. He called George Harrison’s “Something” “the most beautiful love song ever written,” and paid it fitting tribute—an impassioned performance that was touching, too, as a gesture of détente, an olive branch to the sideburned set.

As for your idea that Sinatra has “fallen into the background”—has he, really? By the time of the Duets (1993), the biggest names in rock and soul were lining up to kiss his papal ring. And today, it seems to me, Sinatra has more cachet than he has in decades—and I’m not just talking about Michael Bublé. What about the self-proclaimed “new Sinatra,” Jay-Z? In the hip-hop era, Sinatra-style stardom, the Sinatra swagger, holds an allure it didn’t when rock’s goons and delinquents ruled the roost.

Of course, hip-hop culture enshrines Sinatra for same the reason it does Scarface: To rappers, he’s an O.G., a mafia don with a microphone. Which leads me to your question about Frank: The Voice and ethnicity. Kaplan does a good job telling the story of Sinatra’s flirtation with the mob. (One of the best set pieces in the book is the tale of Sinatra’s 1947 trip to Cuba to perform at a summit of mafia bosses.) Kaplan is insightful, I think, about the psychology behind Sinatra’s goombah entanglements:

What can be made of Frank’s picaresque misadventures: the gun, the gangsters, the beating of the little columnist? … In a way, he was casting himself as a hero in a corrupt world, a little guy up against overwhelming forces. … Even when those forces were benign, they were white Anglo-Saxon Protestant. Certainly one unconscious purpose for Frank’s Havana trip was to reclaim the power of his Italianness. … There is something boyish and wistful about his need to carry that gun, to be accepted among those mostly Italian men of honor. … Frank was a little guy (not a single record exists of his having prevailed in a real fight), and secretly he knew he was an artist, with an exquisite sensibility. How could such a person be a man among men? … As Sinatra’s fame grew and his hangers-on kowtowed and cowered, he came to believe in his own toughness. Yet there was always something artificial about it … he needed the hard shell that guarded the exquisite flower within.

The prose is purplish, but Kaplan’s judgments have the ring of truth. I wish, though, that Kaplan had thought more about the musical manifestations of Sinatra’s “Italianness.” Unless I dozed off and missed something, Kaplan doesn’t write a word about the bel canto vocal tradition. Yet Sinatra must have heard that music growing up in Hoboken’s “Guinea Town.” You can certainly detect the bel canto influence in his sumptuous, legato ballad singing.

And then there’s the surname. One of the key incidents in Sinatra’s life came in 1939, when Harry James asked the young singer to adopt a stage alias. (James’ suggestion: “Frankie Satin.”) Anthony Benedetto changed his name to Tony Bennett; Robert Zimmerman cast off his Jewish name to remake himself as American troubadour Bob Dylan. But Sinatra refused, threatening to walk away from the biggest break of his career: “You want the singer, take the name.” He bore that name with haughty dignity; unlike his friend Dean Martin (né Dino Paul Crocetti), he never dipped into the dialect songbook, playing his ethnicity for cheap laughs—no “Mambo Italiano,” no “That’s Amore.” Sinatra “reclaimed the power of his Italianness” every time he strode onstage to sing American popular songs with his Old World surname blazing on the marquee.

The most striking part of Sinatra’s ethnic persona is what it leaves out. Reading Frank: The Voice, I was fascinated to learn Sinatra had performed in blackface in his Hoboken Four days. This came as a shock, because for the rest of his career Sinatra wanted no part of the age-old pop music tradition of racial masquerade. Compare Sinatra to Bing Crosby, who as late as 1942 was still blacking up in major motion pictures and who slipped towards minstrelsy whenever he wanted to signal “down home”—his jazzy cadences giving way to slurred, slackened vowels and other “coon song” inflections.

I love what you say, Ann, about Sinatra and Ralph Ellison’s theory of the blues. You’re right; he was a blues singer in the Ellisonian sense—but not the Ellingtonian. Sure, he learned to phrase from listening to Billie Holiday and other African-American musicians. But I’m struck, listening to Sinatra, how little “black” there is in his sound. (Sinatra idolized Humphrey Bogart, and I hear as much of Bogie’s tough-tenderness in Sinatra as I do Lady Day.) Sinatra was an original, who fused a slew of influences, musical and non-, into an idiosyncratic style, inventing a new way sing like, to live like, a white guy. Do we call that style “Italian”? “American”? Or do we just throw up our hands and call it “Sinatra”?

Time to wrap up, and I still haven’t gotten to the ball of wax—the ball of confusion—that is Ava Gardner. I’ll save those muddled thoughts for next time.

The best is yet to come,

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