The American Spectator

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It always seemed strangely appropriate that Frank Sinatra died on the day of the Seinfeld finale— 10 years ago this past May. On a night when America was set to celebrate a sitcom’s elevation of irony to unforeseen cultural heights, it had lost its mythic pop singer, who knew something about irony, too, but who at his best stirred in his listeners a more earnest acknowledgment of longings, losses, and the good life.

On that night, I was more interested in seeing how Seinfeld would turn out than in remembering Sinatra. Like many of my generation (I was born in 1966), I viewed Sinatra as an icon from a musty and dusty age. His music seemed remote, too—the little of it I’d heard, almost all secondhand, in department stores or diners, or fading in and out of movie scenes.

I was still a rock and roll devotee, though my devotion was waning with each passing year. Rock, it seemed, didn’t age with the listener; it aged the listener. A decade later, I’ve finally caught on to Sinatra, though my appreciation likely will never be of the same character as that of his older fans. That’s because I’ll always be a child of the rock era; I can’t get the backbeat out of my head, though I now wish I could. Its absence looms over any music I try to embrace. It’s a testament to Sinatra’s power that he got through to the likes of me, but I wonder whether future generations will continue to find him as compelling.

Music critic Gary Giddins was certainly correct when he wrote that Sinatra “looms over the cultural life of the century,” but he was talking about the last one. “Every generation has to figure him out from scratch,” he writes—but that’s assuming they’ll think it’s worth the trouble. True, reissues of Sinatra’s recordings and multimedia projects, like those commemorating the 10th anniversary of his passing this year, sell well and generate lots of buzz, and usually prompt a quotation or two from a marketing type about how Sinatra is reaching new (that is, young) listeners. It’s difficult to tell with a heavily mythologized figure like Sinatra, though, just what product— the recordings, the image, the biography—is really being sold. Even if Sinatra’s music somehow finds a way to hover over the 21st century, his listeners won’t be hearing the same things.

The risk attached to his kind of singing was that it promised authenticity of emotion instead of its blithe dismissal or the empty technique of the virtuoso,” writes Pete Hamill in his brief book Why Sinatra Matters. “His singing demanded to be felt, not admired. It always revealed more than it concealed.” Yet to rock’s children, whose mother’s milk was the guitar chord of “You Really Got Me,” Sinatra sounded just like the virtuosos Hamill was slighting, his music devoid of the kick-starting violence of rock and roll. Sinatra was all polish and style, drained of emotion and risk, singing preposterously fuddy-duddy lyrics, backed by arrangements heavily scored with strings or by musicians who sounded like they were on work release from the embalmer’s. Rock buried the virtuoso’s technique in a fathomless grave, assuring that generations of listeners would hear something masterful and controlled as repressed and artificial. The curse of rock and roll on young listeners is not so much that it will corrupt their morals and characters, the dominant concern after Elvis arrived and for a good while afterward. With two parents, a kid can survive almost anything, even American popular culture. The real problem is that rock makes music synonymous with sensation, brute force, and emotional release—and renders the absence of such things suspect and seemingly dishonest. The availability of instant gratification in music, like in anything else, fundamentally alters our tastes. Music more complex than rock—a description that covers an enormous landscape—can sound merely confined, devoted to form at the expense of freedom.

And to a rock listener, freedom—as rock defines it, anyway—is the whole ballgame. A song like “Angel Eyes,” from Sinatra’s classic 1958 album Only the Lonely, is a good example of Hamill’s point about emotional authenticity, though it expresses emotion in a more muted fashion than the typical rocker’s lament. The song describes the kind of despair that rockers tend to convey with shouts, screams, or grunts of uncomprehending pain. Sinatra’s performance of “Angel Eyes,” on the other hand, traces a much subtler, quieter course of personal disintegration:

Pardon me but I got to run
The fact’s uncommonly clear
I got to find who’s now the number one
And why my angel eyes ain’t here
Excuse me while I disappear

Rock knows something about such estrangement, but its narrators almost always want the world to know about it, too. There are no shadows or corners of the room; the rock singer must always stand in the center, bathed in spotlight. In “Angel Eyes,” the world goes merrily on its way, and the singer’s anguish is private. The song plays out against the singer’s separation from those who are not in the emotional ditch he inhabits, and he tells them to “drink up all of you people/Order anything you see.” But he’s already gone.

Michael Gray, author of The Bob Dylan Encyclopedia, describes Sinatra’s music as the kind that rock “was born to abolish.” He’s right. The control in every aspect of Sinatra’s work, from the vocal to the delicate interplay of orchestration, takes some getting used to if you grew up listening to “Like a Rolling Stone.” The title track of Only the Lonely, for example, is a kind of symphonic wonder. It opens in a distant flourish of piano that fades in until the singer’s voice emerges from it as if from a despairing haze, to set the album’s premise:

Each place I go only the lonely go…
The songs I know only the lonely know

The precision with which Sinatra delivers the song’s final lines—“…never let love go/For when it’s gone/you’ll know the loneliness/The heartbreak only the lonely know”—adds to the song’s emotional power as he enforces an intricate syllabic rhythm, breaking the lines like a poet. Contrary to rock’s central premise of spontaneous combustion, the song is more devastating because of Sinatra’s devotion to form.

This is not to say that the man wasn’t capable of hitting you over the head with emotion when the spirit seized him. On Sinatra’s 1965 album, September of My Years, released as he was turning 50, he seems to be laying bare the regrets and vulnerability he feels with the passage of time. The album is a song-cycle of exquisite expressions of melancholy and awareness of the receding calendar, without descending—too often, anyway—into bathos or self-pity. The album’s most famous track, “It Was a Very Good Year,” is an over-orchestrated and overbearing song that Sinatra nevertheless turns into a signature performance. More subtle is the album’s finale, “September Song,” in which Sinatra sings as a man whose time is passing—an idea the very antithesis of rock’s dream of an eternal present:

Oh, the days dwindle down to a precious few
September, November
And these few precious days I’ll spend with you
These precious days I’ll spend with you

But blues in the night was just one half of Sinatra’s canon. Younger listeners are more familiar with his swinging repertoire, including such classics as “I’ve Got You Under My Skin,” “Summer Wind,” and “Fly Me to the Moon,” heard at wedding receptions and, for us New Yorkers, hearing the familiar strains of his “ New York , New York” at too many venues to count. Periodic spikes in popularity of ballroom dancing and the late 1990s swing revival helped keep these standards in heavier rotation than classics of melancholia like “In the Wee Small Hours of the Morning” or “Willow Weep for Me.” Sinatra’s gifts are more readily accessible in such songs, not only because you can tap your feet, but because the music brings out his most famous persona—that of the devil-may-care, hard- living Rat Packer. In an era when image is much more than half the battle, this pose still seems relevant, even contemporary.

There’s something else, too, in these swinging songs: Sinatra sounds like an American man, or the way American men used to sound, anyway, back in the days when men wore suits and hats, before presidential candidates danced on ladies’ talk shows, before baseball players talked about psychotherapy and—well, you get the idea. In his famous 1966 Esquire piece, Gay Talese wrote that Sinatra was “the embodiment of the fully emancipated male, perhaps the only one in America.” Forty years on, that’s an enviable title indeed. Younger American men know that this older time existed, and though they mock it easily, their mockery is not always easy to distinguish from envy. Especially when they hear something like “Luck Be a Lady,” in which Sinatra sings, with joyfulness but also a hint of threat: