WHEN FRANK SINATRA DIED A YEAR AGO TODAY, ON May 14, 1998, at the age of 82, newspapers across America reacted with bold headlines. Many carried special supplements devoted to the singer's life. Even so, as Pete Hamill observes, “Much of the language of farewell had a stale, even hollow quality, probably because most of the obituaries had been ready for too many months.”

The broadcast and print eulogies listed song and movie titles, and offered the inevitable recitations of Sinatra's famous feuds and brawls, romances and breakups, busts and comebacks. But, for Hamill, something was missing. “It was difficult, reading and watching all of this, to remember why Sinatra mattered to so many people, and why he will continue to matter in the years ahead.”

In Why Sinatra Matters, Hamill provides the context and depth that was missing last May. This brief but eloquent — and elegantly designed — homage to the singer, equal parts personal memoir and biography, defies easy categorization. Hamill's fascination with Sinatra began in the 1940s, then deepened after they became friends in the 1960s. For Hamill, a talented New York journalist and author, Sinatra's significance lies in his roles as an artist, as an icon of 20th-century American masculinity, and as an exemplar of the American Dream.

“He wasn't,” Hamill notes, simply an entertainer from a specific time and place in American life who lived on as a kind of musty artifact. Through a combination of artistic originality, great passion and immense will, he transcended several eras and indirectly helped change the way all of us lived. He was formed by an America that is long gone: the country of the European immigrants and the virulent America-for-Americans nativism that was directed at them.

Hamill also assays the myriad other elements that gave rise to Sinatra's legend, including his musical influences, his impeccable phrasing, the development of his repertoire, his seemingly effortless (but hard-won) style, his films, his politics (stridently liberal and Democratic until the 1970s) and his relationships with successive generations of fans — even those yet to be born. “The world of my grandchildren,” Hamill writes, will not listen to Sinatra in the way four generations of Americans have listened to him. But high art always survives. Long after his death, Charlie Parker still plays his version of the urban blues. Billie Holiday still whispers her anguish. Mozart still erupts in joy . . . In their ultimate triumph over the banality of death, such artists continue to matter. So will Frank Sinatra.

IN TRACING SINATRA'S CAREER, AND GRAPPLING WITH why he matters, Hamill draws on his own experiences as fan, journalist and friend, as well as on works by other authors. Though two decades younger than his subject, the author, like the singer, grew up in an urban, working-class, ethnic neighborhood (Sinatra among Hoboken Italians, Hamill among Brooklyn Irish). Later, as a journalist, Hamill moved — and occasionally crossed Sinatra's path — in Manhattan social circles that included, among others, saloon owners, show-biz types, tough guys and urban pols. Not surprisingly, Hamill is best when evoking those various shared milieus — and even better when evoking shared late-night drinks with the singer.

Observing Sinatra close-up, Hamill often evokes a smoky lyricism:

Here in one of the late-night places of an all-night city, Sinatra was wearing a dark suit, a perfectly knotted red tie, a pale blue shirt, silver cuff links, and was drinking Jack Daniel's. He was still lean then. The famous face remained an arrangement of knobs and planes that didn't assemble into any conventional version of masculine handsomeness but had an enormous vitality . . . He sat with his back against the wall in the muted light of the room and seemed to ignore his own voice on the jukebox.

Early on, Hamill admits the limits of his firsthand knowledge of his subject. “To be sure, we were not friends in any conventional way; I did not visit his home and he did not visit mine. Only a very few intimate friends ever had such access, and I was certainly not one of them. But I liked him enormously.” When Sinatra's quoted words appear, however, it's often unclear whether Hamill is sharing something that the singer told him, or using another author's work. Endnotes, or more specific attributions — beyond the frequent “Sinatra said” and the list, at the end of the book, of Sinatra-related books Hamill consulted — would have been helpful.

To be sure, Hamill does not intend a formal biography of Sinatra. (The book contains neither index nor footnotes.) Even so, his frequent failure to give sources for quotes — an issue to which such a seasoned journalist should be sensitive — is unfair to the authors whose works he uses. By raising questions of provenance, this omission also blunts the book's authority, most conspicuously when Hamill ventures into areas that still prompt debate, such as Sinatra's reputed ties to the mob, or the means by which, in 1943, he won a release from an exploitive contract with bandleader Tommy Dorsey.

When, for instance, Hamill quotes Sinatra dismissing this or that rumor, is he offering us something new, something that the singer told him, perhaps, late at night, in an unguarded moment after a few drinks? Or is Hamill serving up something from another writer? Or worse, something that Sinatra never said? In an epigraph to one chapter, Hamill rolls out Sinatra's oft-quoted line on religion: “I'm for whatever gets you through the night.” It's a good line. But Hamill should have disclosed that it comes from a 1963 Playboy interview with the singer, an exchange that several Sinatra authorities — most recently Michael Freedland, in All the Way: A Biography of Frank Sinatra — assert was written in its entirety by Mike Shore, a Reprise Records advertising executive.

The book also suffers from an occasional lapse into pedantry, mostly when Hamill strays too far from the subjects he knows best — Sinatra, jazz, New York City, boxing, saloons, politics. A disquisition on the plight of Italian immigrants, for instance, slips into blowhard tendentiousness. (“Americans didn't like Italians. An American was supposed to be white, Anglo-Saxon and Protestant. He was supposed to come from northern Europe.”) In the process, Hamill asserts that Italian Unification took place in 1871 — 10 years after the actual date.

Such shortcomings, however, should not obscure Hamill's achievement. By and large, he succeeds — convincingly, with natty aplomb — in explaining why Sinatra, even now, still matters.

By PETE HAMILL | Little Brown
185 pages | $18 hardcover

SINATRALAND | By SAM KASHNER The Overlook Press | 192 pages
$23 hardcover


OBSESSIONS ARE BY NATURE STRANGE AND HIGHLY personal. Many people, it seems, experience these intense preoccupations — with a musician, a movie star, or any unattainable object — during adolescence, a time when such single-minded ardor is seen as acceptable, even necessary. Eventually, real passions and responsibilities take over most lives, and the former source of infinite fascination is relegated to the land of nostalgia. But some people just can't seem to get beyond their obsessions; their point of reference remains entirely tied to that unattainable someone.

Sinatraland's Finkie Finkelstein is such a man; his life — as the title of this first novel by Sam Kashner suggests — is an homage to his hero, Frank Sinatra. “It's Frank's world,” Finkie declares. “We only live in it.” The story is told as a series of letters from Finkie, who lives in New Jersey and sells window shades for a living, to his idol, who never writes back. Finkie marries a Sinatra fan, names their daughter Nancy Ava, loves every terrible Sinatra film ever made and writes, “William Shakespeare doesn't deserve to carry your jockstrap.” He's a disturbed man whose obsession is in one way or another responsible for his life's many ruinous turns.

If nothing else, Finkie's voice is authentic. “Like you, Frank,” he observes, “I know a lot of people but no one knows me.” A capable writer, Kashner does a good job of conveying the hollowness of Finkie's existence — a little too good: By its midpoint the book is as tedious and dreary as Frank's life is glamorous. Kashner picks up the pace near the end, when Finkie finally achieves the goal of his life, and also his greatest fear: He meets Old Blue Eyes himself. It's a terrible day that leaves Finkie more desolate — and desperate — than ever. This reader kept hoping Finkie would come to his senses. He never does. Consequently, Sinatraland never transcends its inherent frustrations.

–Sara Catania

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