The Book Club

What Sinatra Learned From Billie Holiday

You know, Jody,

There’s one guy James Kaplan probably hates right now: Keith Richards. Here the author spends more than half a decade trousers-deep in the life of one of America’s great pop figures, and some scruffy English upstart grabs the top spot on with an equally thick life story the week the Frank book hits the pavement. Everybody’s talking about Keef’s Life partly because, I’m sure, it’s a great read (I’ve haven’t cracked it yet; been busy with Ol’ Blue Eyes) but also because baby boomers never tire of revisiting the mythologies of their own get-off-of-my-cloud counterculture. Sinatra, who would have been 95 this year, never much liked rock ’n’ roll; and though his style and art certainly influenced the way American men created themselves for much of the century, he’s fallen into the background, I’d argue, in a year when the title of Most Powerful Entertainer went to rocker dude (and Richards disciple) Johnny Depp.

Born into this moment, Kaplan’s giant baby understandably reeks of the currently very potent pheromones of scandal, sexual licentiousness, and extremely fluid notions of propriety. Like the season’s other major piece of period entertainment, the HBO melodrama Boardwalk Empire, Frank: The Voice reminds us that licentiousness and generally loose morals were common decades before the Glimmer Twins flounced onto the scene.

Kaplan’s Sinatra is a fast-moving fish in a shark pool, driven by his sense of singularity, which simultaneously isolated and elevated him; the sexual wanderlust that dominated his personal life (at least until Ava came along) was merely a sensual counterpart to his artistic restlessness. One of my favorite early scenes in the book is the one in which he tells the bandleader Harry James he’s leaving him to work with the more established Tommy Dorsey. Kaplan paints it like the breakup it was, with Sinatra saying he’d “rather open a vein” than dump him, and James reaching out a bony hand for a final squeeze before setting him free.

Sinatra, Kaplan argues, was defined by loneliness, a corny idea that makes me think of Al Pacino sulking, shot through a gauzy lens but one that, for me, resonates with the almost eerie insouciance—sometimes it leaned toward detachment, at other times, fatalism or even cruelty—that runs through all of Sinatra’s work. I’ve read accounts of those bobby-soxers fouling theater seats before, and, like you, Jody, I was happy to learn that Swoonatra had his own Brian Epstein in the person of the gone-too-young George Evans. Still, I’m not sure if I buy that pure heat is what made the girls go mad for Frankie. He may have been a torch singer—you argue that beautifully—but even in his 20s, the flame he burned was cool and blue at its core.

Kaplan lays out the sources of Sinatra’s early style: the Bing idolatry, the lessons in vocal harmony he learned as part of the talent show-winning Hoboken Four, an interest in classical music that only grew deeper with time. He also mentions, more than once, the debt Sinatra owes to Billie Holiday. Typically for Kaplan, he defines that connection as sexual, suggesting that Frank not only wanted to score with Billie (though he never did), he worked to capture how she “brought sex—painful, longing sex—into every syllable of her songs.”

I find the Sinatra-Holiday pairing irresistible, but not as some fantasy porn scene. What distinguished both singers, I think, wasn’t carnality but headiness. These are supremely intelligent singers, pensive to the core; the exquisite torture in their sad songs, and the pleasure felt in their celebrations, comes from their almost burdensome genius for reflection. Listen to each sing “You Go to My Head,” for example: Billie reads the song’s extended metaphor as a chance to go quietly champagne-giddy, while Sinatra opts to communicate risky reverie, a subtle mix of distractedness and compulsion.

It seems to me that what Sinatra learned from Lady Day and the black jazz musicians whom Kaplan says he greatly admired (without, frustratingly, elaborating further) was the dignity that lies at the heart of 20th-century cool—a pride that establishes itself in response to, but not in denial of, being marginalized and disrespected. As you’ve said, Frank: The Voice compellingly presents Sinatra as the product of his immigrant forebears, but I would have liked more on how that sense of himself made him, in essence, a blues singer—if we define the blues as Ralph Ellison did, as “the only consistent art in the United States which constantly remind us of our limitations while encouraging us to see how far we can actually go.”

Sinatra was not an invisible man, yet Kaplan meticulously builds the case for viewing him as someone who never quite felt at the center of his own life—as a man’s man who nonetheless never could fully claim patriarchal privilege. I like the way that this Frankie, slight and slippery, contradicts that hoary old idea of the man in the fedora as a role model for conventional masculinity only now being usurped by one Don Draper. Music is the great destabilizer, freeing our hearts and moving our hips and shocking us into new ways of thinking. As one of its great modern practitioners, Sinatra had to be a more ambiguous figure than the prevailing stereotypes about him allowed. What I like best about this book is that it makes an attempt to grasp this radical instability while still making time for a thorough appreciation of Sinatra’s many graspable strengths.

I had the same problems as you with Kaplan’s odd attempts to mind-meld with his subjects. I just don’t buy many of the passages where he projects into the minds of Sinatra and his coterie. Kaplan passes moral judgment too often, as well—strange in a book that bares all about loosey-goosey Old Hollywood. Why does he come down so hard on occasional Sinatra flame Lana Turner, whom he portrays as some kind of spiritual black hole? What’s with his fixation on the perennially wronged Nancy Sinatra and the pretty brown gloves she wore to divorce court? The asides about the mistreatment of women by friends like the “self-confessed sex addict” and songwriter Jimmy Van Huesen—as well as by Frankie himself—left me feeling creepy, too. Kaplan drops rumors of physical violence and even rape within Sinatra’s cohort, calling them “malodorous bubbles in a swamp”; I would have preferred a more systematic consideration of the artist’s attitudes toward the women he loved, used, and apparently sometimes came to hate.

I haven’t gotten to all of your questions yet, but let me raise a few of my own. I’m interested to hear what you, so well-versed in pop-cult expressions of ethnicity, think of how Kaplan portrays Sinatra’s explorations of his, ahem, Italian heritage. Kaplan’s view of Frankie’s gangster lean is interesting, but how accurate do you think it is? And then there’s Ava. We gotta talk about Ava. Just thinking about her tires me out.

I think of you,

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