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The Boston Phoenix Frank Sinatra: 1915-1998

Discovering the man and his music.

By Jon Garelick

MAY 26, 1998:  "You know how you can chart the course of your life by hearing certain songs?" asked Diane Sawyer on Turning Point last year. "Well, think how many of them were sung by Frank Sinatra." To which one might ask, Sinatra-like, "Whose life, Diane, baby?" Could Sawyer have been speaking to anyone born after 1965? Which songs did she mean, exactly? "Strangers in the Night" (1966)? "Something Stupid" (1967)? "Theme from New York, New York" (1980)? For many older Sinatra fans, the platinum-selling Duets (Capitol, 1993), was a sad joke -- Sinatra sounded bad, and Bono didn't sound much better. Yet it sold. And it was supposed to represent not only Sinatra's enduring artistry, but also his triumph with the MTV generation (a triumph coolly exploited by his younger colleague, Tony Bennett). Still, it was a headscratcher. "I find it hard to believe," one local Sinatra-ophile said to me, "that some kid is going into Newbury Comics and asking for Nevermind and 'Oh yeah, that Frank Sinatra Duets CD.' " When that same kid is feeling miserable, is he going to put on "Something in the Way" or "I'm a Fool To Want You"?

"The songs he sang will be Frank Sinatra's legacy," read a Boston Globe editorial. "The rest is footnotes." But you have to wonder. The songs might be the hardest thing for subsequent generations to hear. For most of them, I would suspect, Sinatra is a lounge-era cultural artifact -- he's Vegas and tuxedoes, JFK and Playboy magazine. Stephen Holden, in his rather defensive whine in the Times, may have had it right: "To the generation that has reinstated martini drinking, cigar smoking, and golf as social rituals, the era of the Rat Pack looms as a golden age of bad behavior without consequences." For Holden, this misappropriation of Sinatra's legacy condescends to the man and his achievements. Sinatra, he laments, has become just as much a figure of camp as the Elvis Presley of the over-stuffed jumpsuits and bacon-and-peanut-butter subs. For many people, Sinatra is at best a misogynist, at worst a gangster. To the indifferent, he's simply the cultural joke of the old Phil Hartman impersonations on Saturday Night Live (based on Sinatra's response to George Michael's lament on the difficulties of fame: "Come on, George. Loosen up. Swing, man.").

"The music is what's important," people are saying now. But to the rock-and-roll generation, Sinatra's music has been an acquired taste. The Beatles ushered in the concept of the singer/songwriter, and the music of Bob Dylan (who attended a special Sinatra 80th-birthday tribute) would seem to be a revolt against everything Sinatra represented. Sinatra was first and foremost an entertainer. Every rock singer after Dylan has been an "artist." The "great American songbook," which Sinatra (along with Ella Fitzgerald and a few others) helped invent, owes as much to the European art song as to blues and jazz. Rock leans more toward folk and blues. Sinatra's formal presentation is that of the entertainer who stands apart, in which he plays a character scripted for him by a songwriter. But rock -- in the folk-music tradition -- blurs the distinctions between artist and audience; self-expression is all, and assumptions about "technique" are continually redefined. Sinatra, however adolescent his private behavior, performed for the last 40 years of his career in the persona of the sophisticated adult. Rockers, almost by necessity, have to play the disaffected youth well into middle age.

So it's worth reiterating what exactly Sinatra did leave behind, and why his music is worth learning. He led his own revolution. Rock and roll may have been a revolution against the Sinatra style, but in his own way, Sinatra anticipated rock and made it possible. From his hero Bing Crosby, he learned how to use the microphone as an instrument. He adapted the intimate crooning style of Crosby to a new conversational kind of swing, and a broader range of emotion, combining it with Billie Holiday's improvisational depth and Mabel Mercer's fidelity to the text. Sinatra sang other people's songs but turned them into his life story. For the first time, fans identified with a singer as they would later with rock stars. "I was the boy in every corner drugstore who'd gone off, drafted to the war," he said of his youthful popularity. "That was all." But that emotional identification between artist and audience endured. At Capitol Records, he virtually invented the "concept album" with arrangers like Nelson Riddle, Billy May, and Gordon Jenkins. Invisible, perhaps even to his own fans, was the amount of work Sinatra put into selecting and sequencing his material, hand-picking arrangers and session men, even ordering up new songs when he needed them to complete the mood of a particular album. (There's no better picture of Sinatra the working musician than in Wil Friedwald's Sinatra! The Song Is You: A Singer's Art.) On a more mundane note, when you see a punk smoking and drinking on stage, remember that Frank was there first ("another way of flaunting his invincibility," says the vocal coach David Craig in John Lahr's Sinatra: The Artist and the Man).

So it makes sense that the people from the rock era who most readily identify with Sinatra are vocalists: Bono, even Dylan -- not merely rockers, but artists who know about the challenges of vocal performance, and are also the most aware of their artistic mortality. Not long ago, I was watching a video of Sinatra: A Man and His Music, the TV show Sinatra made in 1965, when he was turning 50. Gay Talese reported the backstage life of that show in a piece he wrote for Esquire, "Frank Sinatra Has a Cold." In it, Talese dramatized how the condition of Sinatra's throat and sinuses -- in short, his voice -- could plunge the singer into a depression that in turn caused "a kind of psychosomatic nasal drip" among his dozens of associates and hangers-on. Sinatra battled the cold as he was taping the show and finally triumphed.

As we watched that show -- Sinatra entering a darkened, empty soundstage, then belting out "I've Got You Under My Skin" -- one of my friends remarked, "He goes from zero to 60 in no time." Then she added, "I can see why he wouldn't want to do this with a cold: his voice is right out there, he's totally exposed." Sinatra, in the midst of one of Cole Porter's suave fever dreams, took a deep breath and exhaled: "And each time I do just the thought of you makes me stop right before I begin" -- a breathless aside, delivered in one breath -- and then the coda: "Because I've got you/Under my skin."

As a vocalist, swinging or not, Sinatra traded in tragedy. His voice, more worn and heavy after his 1953 comeback, was suitable to grown-up concerns. He was no longer, writes Lahr, "the gentle boy balladeer of the forties. Fragility had gone from his voice, to be replaced by a virile adult's sense of happiness and hurt." Mutability was always there. His range wasn't huge, which made his leaps for high notes all the more dramatic, and you can hear his vocal color change from album to album. There was iron in his voice, and velvet, too. It was a strong voice that could convey the sound of weakness and hurt, that could make you believe the hippest, most powerful guy in show biz ("I've got the world on a string!") was also the most hurting ("Willow, weep for me!"). At times, the results are paradoxical. Sinatra claims helplessness in "I've Got You Under My Skin," but he seems to enjoy the feeling, and his delivery is so powerful that the effect is closer to "Under My Thumb."

Whether you can hear Sinatra's artistry or not, his cultural presence is as unmistakable as Elvis's. Greil Marcus made the argument in Dead Elvis: love him or hate him, he's everywhere. After finishing that book, I realized just how pervasive Elvis was. I couldn't get through a day without catching some reference to him somewhere: on a postage stamp, at a garage sale, in passing conversation. Sinatra got there long before Presley. He was on TV, in movies, on the radio. Put on a cheeky attitude and you were likely to get challenged: "Who do you think you are -- Frank Sinatra?" Even Twyla Tharp fashioned a series of ultra-mod pieces in his honor. Bono was right at the Grammys: "You know his story because it's your story. Frank walks like America." Sinatra has that connection with Elvis, and with punks everywhere, because America is a country where everyone's trying to pass, from the freaky white trash kid in Tupelo, Mississippi, to the skinny dago in Hoboken.

In Lahr's portrait, Sinatra is the outsider who wants in, who feels awkward, unsophisticated, but achieves a kind of grace through song. Lahr writes that the songwriters Sinatra embraced "were the voices of the educated middle-class mainstream, whose sophisticated wordplay, diction, and syntax had an equipoise and a class that contrasted with the social stutter that so bedeviled Sinatra." The irony is that so many of these sophisticated, middle-class songwriters were second-generation paisans like Frank: Sammy Cahn, Ira Gershwin, E.Y. "Yip" Harburg, Arthur Schwartz, Jerome Kern, Lorenz Hart -- Jews trying to put one over on the goyim.

So Sinatra's was the ultimate American story -- the man who flaunts his ethnicity, displays his "hot" anti-social emotions, plays blackface minstrel games with his pals Sammy and Dean -- but at the same time exudes assimilated social grace and glib sophistication. For every story of his crudity -- and even cruelty -- there's an equally convincing story of unfettered generosity and loyalty. It's a story about becoming "white" while never forgetting where you come from. ("These are guys who gave me jobs when no one else would," Sinatra said about the Mob.) The songs were Sinatra's way of talking the talk. In time, his mode of speech will become as remote as Louis Armstrong 1927, Robert Johnson 1936, Charlie Parker 1947 -- and just as worth learning.

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