n 1947, E.J. Kahn Jr. published The Voice: The Story of An American Phenomenon, a 125-page book based on a multi-part profile of Frank Sinatra that had appeared in the New Yorker the preceding year. “Sinatra’s fans are overwhelmingly young women,” Kahn wrote in the magazine’s signature tone of slight condescension. “Their versions of the effect he has on them are, on the whole, more daintily phrased than the callous judgments of the psychologists.”
The Voice was the first book to be published about the man who is now generally regarded as the greatest popular singer of the 20th century. Not until 1961 would another full-length volume about Sinatra come out, but since then he has been the subject of books of every possible kind: worshipful coffee-table scrapbooks; sleazy “unauthorized” biographies; tell-all memoirs by friends, family members, and former employees; meticulously researched discographies; scholarly monographs and essay collections; even children’s books. No American popular musician has been written about so extensively—or so uncomprehendingly. He is a signal figure of American culture, yet few who write about him seem to understand why.
David Lehman’s Sinatra’s Century: One Hundred Notes on the Man and His World, published to commemorate the centenary of Sinatra’s birth, is the most recent in a long string of short books that conform to a now-familiar pattern set in 1998 by Pete Hamill’s Why Sinatra Matters, which was published to commemorate Sinatra’s death earlier that year. A poet and critic by trade, Lehman has composed a paean that devotes as much space to Sinatra’s personality as to his singing, and in which he is viewed through the prism of the middle-aged author’s life and experience: “Everyone else I knew was listening to the Beatles, the Rolling Stones, the Kinks, the Mamas and the Papas, and the Lovin’ Spoonful. I liked them, too, but a singer from another generation was singing the music in my heart.”
Well-written and unfailingly pleasing to read, Sinatra’s Century reveals little about Sinatra that most of his admirers don’t already know. Not so Sinatra: The Chairman, the second installment of James Kaplan’s two-volume biography, a mammoth undertaking (taken together, the two books total 1,765 pages) designed to be the definitive primary-source biography an artist of Sinatra’s significance deserves.* But the ambition of the design is not fulfilled by the unsatisfactory results. Sinatra: The Chairman and Sinatra: The Voice, its 2010 companion volume, prove on closer inspection to be a mixture of verifiable fact, dubiously sourced gossip, and pure speculation. They are the product of a celebrity journalist and sometime novelist who knows how to tell a juicy story—but who writes with a coarseness that conjures up not Sinatra’s voice but the legendarily pretentious liner notes that accompanied many of his albums.
Kaplan is also musically ignorant: His biography is akin to a thousand-page life of Beethoven that says nothing of value about his symphonies.** This is true, of course, of almost every book ever published about Sinatra, but since his music is actually the reason why his life matters, Kaplan’s exhaustive chronicling of his subject’s bad behavior simply seems somewhat beside the point.
Sinatra seems to have feared being seen as weak more than anything else, even though he had to rely on bodyguards to follow through on his spur-of-the-moment threats.
aplan’s Sinatra is an artist of hypertrophied sensitivity born into a working-class New Jersey family—and a male-dominated Italian-American culture—in which sensitivity was not an advantage but a liability. In addition, he was slight of stature and had a face that bore the scars of the forceps of the obstetrician who delivered him, enough so that he resorted to wearing pancake makeup throughout his life to conceal the scars, just as he wore lifts in his shoes to make him look taller.
All these things set the young Sinatra apart from the other members of his family and the people in the urban community in which he grew up, most of whom put a high premium on toughness and physical beauty. It stands to reason that he would later find intimacy to be difficult to the point of impossibility and became notorious for his unwillingness to apologize for anything that he did, however cruel or inconsiderate. More than anything else, he seems to have feared being seen as weak, even though he had to rely on bodyguards to follow through on his hot-tempered spur-of-the-moment threats. (“Sinatra saved my life in 1967,” the comedian Shecky Greene joked. “Five guys were beating me up, and I heard Frank say, ‘That’s enough.'”) Therein lay the source of his persistent attraction to Mafia bosses like Sam Giancana, which Kaplan sums up in a single pithy sentence: “He idolized them all his life, much as a small boy might idolize cowboys or soldiers.”
If his sensitivity had been less extreme, his personality might well have been more equable and his art more balanced. Instead he treated most of his friends, lovers, and colleagues at one time or another with an alcohol-fueled capriciousness that was so manically, violently unpredictable that one of his intimates, the songwriter Jimmy Van Heusen, referred to him as “the monster”—simultaneously making classic albums like In the Wee Small Hours of the Morning (1955) and Only the Lonely (1958) in which he sang songs of failed love with near-suicidal intensity.
Only in the recording studio and (sometimes) on stage was Sinatra prepared to acknowledge his vulnerability. There he was esteemed for his sensitivity, and all who worked with him agreed that he was not merely a great singer but a great musician as well. Surviving recordings of his studio rehearsals show that he had a phenomenally exact ear that made it possible for him to act for all intents and purposes as his own producer. And though he could not read music, the infrequent occasions on which he led the orchestras that accompanied other singers (most notably Peggy Lee, for whom he conducted the 1957 album The Man I Love) leave the knowledgeable listener in no possible doubt that he was not a mere stick-waving amateur but a true professional who was fully capable of directing an instrumental ensemble.
Kaplan fails to do justice to Sinatra’s deep-seated aesthetic sensibility. He tells us little, for instance, about the passionate devotee of classical music (his favorite composer, unlikely as it may sound, was Ralph Vaughan Williams) and nothing at all about the amateur painter who worked in an austerely abstract style influenced by Ellsworth Kelly. In The Chairman, by contrast, the reader is far more likely to encounter Van Heusen’s viciously bullying monster—though that unsavory figure was no less “real” than the poet who lavished on “Laura” and “Night and Day” the same interpretative skills that a classical vocalist like Dietrich Fischer-Dieskau brought to the art songs of Schubert and Wolf. Kaplan’s sin is one of disproportion, not distortion: Sinatra wasn’t always bad, but when he was bad, he was by all accounts appalling beyond belief.
While Sinatra scarcely ever misbehaved in the recording studio, he conducted himself like a spoiled child on the sets of his movies, habitually refusing to film more than one or two takes of a scene, and many of the actors and directors with whom he worked came to the reasonable conclusion that he simply didn’t take acting seriously. This point of view is supported by the fact that his only truly memorable dramatic performances were given in the handful of first-rate films that he made, in particular From Here to Eternity (1953), The Man with the Golden Arm (1955), and The Manchurian Candidate (1961), in all of which he was extraordinary. In lesser fare, by contrast, he gave lesser performances, suggesting that he lacked the true professional’s pride in craft.
Still, the actor Robert Wagner argued that there was another reason for Sinatra’s unwillingness to film multiple takes: “Frank was very conscious of his lack of training; he was never sure that he would be able to reproduce an effect more than once or twice because he had to rely on emotion more than craft.” This is consistent with all that we know about his lifelong inability to admit and exploit his vulnerability, something that every trained actor learns how to do as a matter of course. For much the same reason, Kaplan explains, he was a failure on TV, on which he came across as arrogant and humorless: “The jokes he made…usually carried an undertone (or an overtone) of anger.”
ven as a singer, Sinatra had his limits. Intensely musical but nonetheless primarily text-oriented, he was incapable of improvising in the manner of jazz singers such as Ella Fitzgerald (whom he admired extravagantly). Following the example of Billie Holiday, whom he cited as “the greatest single musical influence on me,” he preferred to decorate and paraphrase existing melodies instead of making up new ones of his own. Most of the time he did so to brilliantly apposite effect, but when he sang in a pure jazz context, he sometimes found himself at a loss.
“There’s a certain squareness about Frank,” said Bill Miller, Sinatra’s longtime accompanist. That was never more in evidence than when he worked with Count Basie’s band. Unable to float naturally atop Basie’s straight-ahead swing, he tried too hard, singing with the same over-emphatic, almost awkward syncopation that could also be heard when he performed Cole Porter’s “Well, Did You Evah!” on screen in High Society with Bing Crosby, whose seemingly inborn jazziness made Sinatra sound stiff. Nat Cole, who was a major jazz pianist before he became an equally major popular singer, neatly summed up what is missing from these performances: “The band swings Frank. I swing the band.”
In the right setting, of course, he could swing effortlessly, but usually only when accompanied by a big band with strings whose rhythm section played with a light two-beat feel, shifting into straight four-four time at the climaxes. Nelson Riddle, Sinatra’s most compatible arranger, wrote that way for him in such celebrated charts as the version of Porter’s “I’ve Got You Under My Skin” included on Songs for Swingin’ Lovers that the two men recorded in 1956. No one listening to this galvanizing performance could possibly doubt Sinatra’s sympathy for jazz.
“I’ve Got You Under My Skin” also illustrates another of his stylistic tics, the alterations that he made to the lyrics of the songs he sang (“In spite of a warning voice that comes in the night / And repeats—how it yells!—in my ear”). Most of the time they are effective enough, but on occasion they are wince-makingly gratuitous. In one of his few penetrating comments on Sinatra’s music, Kaplan singles out the moment in the 1963 remake of the Riddle-arranged 1958 recording of “Witchcraft” when the singer changes Carolyn Leigh’s “wicked witchcraft” (which he had previously changed to “that crazy witchcraft” in the original recording) to “that coo-coo witchcraft.” The effect of this “hip” alteration, Kaplan correctly notes, is “to cheapen the line and focus attention on the singer as a celebrity rather than on the song itself.”
Such lapses of taste were comparatively rare in the studio, but they grew increasingly common in Sinatra’s live performances, which too often betrayed the vulgar streak in his personality. So, too, did the fact that he sang with what the songwriter Gene Lees described as “almost Oxonian vowels” but spoke (and acted) in a dese-dem-and-dose accent redolent of the streets of New Jersey.
All of which is indicative of just how endlessly complicated Frank Sinatra was. It stands to reason that so many books should have been written about him, because he was so many men, foremost among them the Everyman who gave voice to the sorrows of everyone who heard him perform with exquisite delicacy such despairing saloon songs as “One for My Baby (And One More for the Road).” “Hearing him sing this way…you forget that he is any man but this man,” Kaplan writes in The Chairman.
Yet the other Sinatras were always there, too: The singer who helped to codify and establish the immortality of the American songbook was the same man who reportedly used a knife and fork to eat ham and eggs off the bosom of a Miami Beach prostitute while filming Lady in Cement, one of his worst movies, in 1968. He was a poet and a monster, a swinger and a square, a toweringly eloquent artist and a scared little boy, and I doubt a time will ever come when we lose interest in trying to figure him out.
Because Kaplan is more interested in the monster than the poet, he basically brings his chokingly prolix biography to an abrupt end with Sinatra’s abortive 1971 “retirement” concert. The last quarter-century of Sinatra’s life was far less scandalous—given his increasing age, it could hardly have been otherwise—and so Kaplan crams it into a 35-page “coda” that ends with the singer’s death in 1998. But as far as the history of American music is concerned, those years were anything but insignificant. After a decade of decline in which rock-and-roll seemed to be obliterating the classic American pop song, thereby making Sinatra feel so out of date that he declared himself a back number and announced that he was done with performing, he came roaring back, reinventing himself as a sports-stadium singer who drew rock-sized crowds by singing the very same standards that had long since been driven from the airwaves by the Beatles and the Rolling Stones.
At the same time, younger singers as dissimilar as Willie Nelson, Harry Nilsson, Linda Ronstadt, and Bryan Ferry recorded wildly successful albums of golden-age standards in the 1970s and early 80s, all of which evoked in variously personal ways the Sinatra style. And though the man himself was by then in somewhat ragged voice, he issued one last enduring recording in 1980, the “past” panel of the three-disc Trilogy, in the process single-handedly turning the theme song from Martin Scorsese’s New York, New York into something akin to a local national anthem.
As a result, Sinatra ended his life not in sad and shameful disgrace, which had been Kitty Kelley’s purpose in writing her scabrous hatchet job, but as a universally celebrated, even beloved artist of the first rank—one whose definitive biography still waits to be written.