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Between a Rock and a Sinatra

Catching on to the Chairman of the Board's greatness after a lifetime of rock and roll.

By From the October 2008 issue

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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:

Let’s keep this party polite
Never get out of my sight
Stick with me baby, I’m the guy that you came in with

They might be reminded of how constricted they are in their dealings with the fairer sex, even as, it seems, all the barriers have come down. Part of Sinatra’s old-style manliness was also about sophistication and knowingness, of course; his up-tempo music (always played by the top hands in the business) exudes a class and refinement that rock, devoted to spirit over craft and rooted despite its best efforts in the adolescent, simply does not possess.

I’m not sure Sinatra ever quite convinces us that he is as happy as the music and words of these songs instruct him to be—more often than not, the joy seems fleeting, as in “Summer Wind”—but the sense of five-carat style and once again, mastery, come through. That mastery, so evident to older listeners, can still sneak up on Sinatra’s lost generations.

It happened the night of my own wedding reception, when, watching my bride dance with her father to “Summer Wind,” it occurred to me that Frank Sinatra was undefeated, stronger than rock.

AND YET, TO TWIST the words of Andrew Marvell: at my back I always hear rock’s wicked guitars thundering near. This past summer, the wires carried news of the death of Bo Diddley, one of rock’s pioneering instrumentalists and bandleaders, who created a syncopated guitar style that is routinely copped, in song after song, right up to the present day. I read a few obituaries and then headed over to YouTube, where I saw an astounding video of Diddley performing “Road Runner”—barely a minute and a half of intoxicating, percussive rhythm. It was almost enough to make me forget why I’d turned away from rock in the first place. And to be fair to rock, it’s not just a backbeat that Sinatra’s music lacks. It’s words that sound like they could be spoken by characters in today’s movies and songs. However crude or simplistic many rock lyrics were, and however self-conscious and pretentious they have become (especially in comparison with those of the Gershwins or Cole Porter), it’s also true that rock’s informal, profane, hipster vocabulary was the language of at least the last third of the century.

Regardless of the tiresome debates about the literary value of rock song lyrics—which invariably become a debate, really, about the literary value of Bob Dylan song lyrics, the only ones worth arguing about—there’s no point denying that Sinatra’s remoteness from a younger audience has to do not just with how he sings, but what he sings. While he was releasing September of My Years, Dylan listeners were hearing this:

Now Ophelia, she’s ’neath the window For her I feel so afraid
On her twenty-second birthday
She already is an old maid
To her, death is quite romantic
She wears an iron vest
Her profession’s her religion
Her sin is her lifelessness

That makes for a steep linguistic contrast with Sinatra’s instruction that, say, love and marriage go together like the horse and carriage. Hearses can ride in carriages, too, and to younger ears, accustomed by now to all manner of wordplay in rock songs, such lines sound stale and dead. I’ve winced at my share of Sinatra lyrics. Only the singer’s skill compensates—that is, assuming the listener considers such singing compelling in the first place. If he doesn’t, then he is left with a dead singer singing dead words.

Sinatra expressed his own views about rock early on. Speaking in 1957, he made himself infamous among the younger crowd by declaring that “Rock ’n’ roll smells phony and false. It is sung, played and written for the most part by cretinous goons and by means of its almost imbecilic reiteration, and sly, lewd, in plain fact, dirty lyrics…it manages to be the martial music of every sideburned delinquent on the face of the earth.” He never renounced this judgment, though in time he covered some pop-oriented material, including George Harrison’s “Something,” which he remarkably called one of the greatest love songs ever written. Near the end of his life he consented to the novelty album Duets, featuring the likes of Bono, Anita Baker, and others who sang along to his pre-recorded renditions. The album, which became a top-seller, was an ingenious bit of marketing, if not music, and it also made clear that the old musical divisions were breaking down. His views of their work aside, aging pop royalty had come to crave the Sinatra affiliation, a professional way of marrying up.

Yet even when they paid him tribute, the rockers could never let go of their self-regard. At a televised 80th birthday tribute in 1995, Bruce Springsteen praised Sinatra’s music for evoking a “nasty sense of freedom,” whatever that meant (it sounded like an outtake from “Born to Run”). In an embarrassing tribute at the Grammys a year earlier, Bono celebrated Sinatra for setting an example that rock stars wanted to emulate: that is, he had “bad attitude” and snarl and edge, he was a tough guy, and he was not to be “messed with.” Sinatra, Bono seemed to imply, was really a rocker! Rather than acknowledging that Sinatra’s greatness embodied something separate from and mostly incompatible with rock, Bono instead argued that his virtues were really rock’s virtues. It doesn’t get more patronizing than that. The rockers can’t necessarily be blamed for trafficking in Sinatra caricatures that had, after all, been around for decades. But the Sinatra tough-guy persona was much more complicated than the facile public image of a pre-rock and roll bad boy.

Hamill writes that Sinatra “perfected the role of the Tender Tough Guy and passed it on to several generations of Americans…[He] created a new model for American masculinity.” Maybe; it’s difficult to believe that there is a single model, anymore, for American masculinity. But it’s certainly true that Sinatra’s great ballad albums, song after song about the pain of lost love, depict a raw vulnerability, at times even what sounds like helplessness, that is far riskier than what most male pop singers would hazard today—even as, paradoxically, touchy-feely men are so much more in vogue than they were in the 1950s. When a typical wimp singer of today like, say, R.E.M.’s wormlike Michael Stipe, goes groveling in song, nobody is surprised; he risks nothing by exposing himself. Angst is all that he has to sell.

That’s what makes Sinatra’s lost-love music so compelling; he’s no tofu-eater. He hangs out with gangsters, for crying out loud. Yet here he is telling us: I thought I found the gal I could trust What a bust This is how the story ends: She’s gonna turn me down and say, “Why can’t we be just friends?”

The whole tough/tender circle is squared in “One for My Baby,” a classic Sinatra performance. Here the two personas come together: the hard-living guy, alone in the bar after hours, still knocking back the booze, but left alone with the bartender to lament the “end of a brief episode.” And there are those vintage lines at the end that mark off Sinatra’s era from the coming rock age: “This torch that I found/It’s gotta be drowned/Or it soon might explode.” The rock instinct is just the opposite: the torch should be lubricated for maximum flammability, the better to express in a howl that will be regarded, on sheer force alone, as art. And we’re all invited to witness the conflagration, still guided by the predominant aesthetic of the last half-century, as set down by Jack Kerouac: “The only people for me are the mad ones…” If you’re not one of them, you’re not really in the game. To refuse to go mad, to just tip Joe and then walk home alone, seems somehow inauthentic in this rock world. In his music, at least, Sinatra never did go mad, never relinquished control. Among many other things, his work dramatized the great discipline it takes to resist the temptations that loss offers for letting everything go. That’s a long way from the rock vision of following impulse where it leads.

LISTENING TO SINATRA NOW, having come to him so late, feels something like being one of those early middle-aged characters in his great 1950s ballads, who suddenly wakes to discover that the answers he thought he had weren’t answers at all. Or perhaps it’s more like the musical equivalent of realizing that your father was right all along. After the initial sheepishness, a certain satisfaction, even liberation, results, and Sinatra’s music becomes a great undiscovered thing about middle age, a strong and unexpected bulwark to hold up against the advancing years, its pedigree matchless, its worth already proven.

But it’s altogether different from the exuberance of youth, when it was you who knew better, and your poor old man who didn’t know diddley.

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About the Author

Paul Beston is associate editor of the Manhattan Institute's City Journal.