Frank Sinatra is the Mount Everest of show business. For decades, journalists, biographers, jazz and movie critics, and gossips have launched themselves at the summit, striving to capture the tantalizing blend of “Lucky Luciano and Michelangelo,” to quote one musician, that made Sinatra such an electric figure in American popular culture.
The New Yorker’s E.J. Kahn was the first, in 1947, just a few years after the famished-looking boy idol convulsed all those bobby-soxers at the Paramount. Then there’s Gay Talese’s classic 1966 Esquire profile “Frank Sinatra Has a Cold,” Pete Hamill’s 1998 pocket gem “Why Sinatra Matters,” Kitty Kelley’s 1986 not-quite-tell-all “His Way,” and many others, worthy and unworthy of their elusive subject.
By David Lehman Harper, 268 pages, $24.99
SINATRA: THE CHAIRMAN
By James Kaplan Doubleday, 979 pages, $35
Sinatra would be 100 years old this Dec. 12 had he not, in his own pet locution, “gone to the mountains” at 82 on May 14, 1998. Timed to the centenary, two volumes have just been added to the buckling library shelves. One is “Sinatra’s Century,” poet David Lehman’s slim meditation on the singer in 100 epigrammatic pensées. The other is “Sinatra: The Chairman,” the second volume of James Kaplan’s gargantuan biography (following “Frank: The Voice,” from 2010), lumbering in at 883 pages of text, not counting endnotes and index. That any popular entertainer could inspire such different biographical treatments—much less nearly 1,700 pages of a two-part study published over five years—confirms Sinatra’s death grip on the American imagination.
Mr. Lehman appears to have listened to cuts from each of Sinatra’s nearly 600 recording sessions, watched most of his 50-odd movies and his countless TV shows and specials, and read deeply in the bibliography. A fan, Mr. Lehman pronounces Sinatra “the greatest of all popular American singers,” his work “an aesthetic experience of intense pleasure,” and the star no less than “the most interesting man in the world.” He compares Sinatra’s 1958 recording of the Harold Arlen-Johnny Mercer lament “One for My Baby (and One More for the Road)” to Hemingway’s pitch-perfect story “A Clean Well-Lighted Place,” about a forlorn, tipsy old man reluctant to leave a Madrid cafe. Sinatra’s ballad, Hemingway’s nihilistic tale and the sight of Humphrey Bogart stood up in the rain by Ingrid Bergman at the Gare de Lyon in “Casablanca,” he writes, are “what American existentialism, as a mood or an aesthetic condition, is all about.”
Happily, most of Mr. Lehman’s Sinatra appreciation is on a less cerebral plane. He ticks all the familiar biographical boxes: mother-ridden boyhood in Hoboken, N.J., bobby-sox mania, career eclipse, Ava Gardner, movie stardom, Rat Pack shenanigans, mob and Kennedy connections, master of sex, sad decline. But, like a good rewrite man, Mr. Lehman holds the reader by ferreting out of the voluminous files lots of choice quotes and anecdotes that reanimate Sinatra’s gamy lost world.
Here is Ava Gardner proclaiming, “He weighs 120, but 110 of those pounds are pure c—k.” Here is movie mogulLouis B. Mayersobbing as he watches young Sinatra belt out “Ol’ Man River” in 1943 at the Hollywood Bowl. And there’s Sinatra’s first glimpse ofDean MartinandJerry Lewis’s smash comedy act: “The Dago’s lousy, but the little Jew is great!” Or screaming in a Hollywood restaurant atMario Puzo,the author of “The Godfather,” with its portrayal of a mobbed-up crooner many thought was based on Sinatra: “Choke. Go ahead and choke, you pimp.” In his final days, Sinatra watches the 1955 movie version of “Guys and Dolls,” in whichMarlon Brandogot the role he coveted of the suave gamblerSky Masterson,and complains to his daughter, “He still can’t sing.” Like a pharaoh, he is buried with provisions for the next world: a flask of Jack Daniel’s.
One anecdote is worth rendering at length as a hallmark of the Sinatra “machismo” that Mr. Lehman can’t help admiring. The lyricist Sammy Cahn relates the story of Sinatra once bragging to his skeptical entourage, “ ‘Who do you think is going to walk into this room?’ and he named a lady who will be one of the great luminaries of the screen as long as movies are made.” She “walked in, smiled demurely, allowed Sinatra to take her hand and lead her into the bedroom.” The author continues: “The lady . . . has been identified as Marlene Dietrich, who is also supposed to have called Frank ‘the Mercedes-Benz of men.’ ”
If Mr. Lehman’s book is an artful miniature portrait, Mr. Kaplan’s second volume is a hand-stitched tapestry with many, many recurring motifs. It is so obsessively detailed that in homage to Mr. Talese’s famous profile it could be subtitled, “Frank Sinatra Has a Hangnail.” Sinatra can’t make a record, movie, date or faux pas, have a sold-out triumph in Las Vegas or a tantrum, or spend another morose night with Jack Daniel’s without Mr. Kaplan recording it. The remarkable thing is that Sinatra’s career is such a compelling transit of the 20th century in American entertainment and politics—and an early and prophetic blending of the two—that the endless Kaplan book is endlessly engaging.
His Sinatra is a magnificent monster—imperious and callow, thuggish and tender, an exquisitely lonely man forever surrounded by a posse of hangers-on; a pop and jazz singer capable of sublime musicianship who couldn’t read music; a natural actor who could follow a star turn in “The Manchurian Candidate” with a Rat Pack stinkeroo like “4 for Texas”; a macho man others idealized who was in thrall to Dean Martin, the gangster Sam Giancana and John F. Kennedy; a sex machine who carried a torch for the gorgeous, drunken, profane Ava Gardner for 40 years.
Mr. Kaplan’s treatment of Sinatra’s recording sessions could be a book in itself. Using studio tapes, outtakes and production notes, he documents dozens of individual recordings, discusses the artistry and quirks of the arrangers Sinatra worked with over the years, especially the moody, brilliant Nelson Riddle, and even logs nearly every “clam”—sour note—the perfectionist ever hit. Describing Sinatra’s 1964 recording of “Secret Love,” which had earlier been a wholesome hit for Doris Day, Mr. Kaplan writes: He “gave the tune a slight edge of world-weariness . . . somehow managing to make you believe that in a relentlessly publicized life he’d actually managed to have a secret love.” Sinatra, it turns out, hated his sentimental late-career smashes “My Way” and, especially, “Strangers in the Night.” “Frank always thought it was about two fags in a bar,” a crony testifies.
The music is central to “Sinatra,” as it should be, but the singer’s artistry is hard put to compete with Mr. Kaplan’s equally encyclopedic accounts of his movie career, sex life and infatuation with the Rat Pack—or “the Clan,” as they sometimes styled themselves—the Kennedys of Camelot and the mob.
As fastidious as he was about his singing, Sinatra could be slovenly about his movies. Gifted directors like Fred Zinnemann (“From Here to Eternity”), Otto Preminger (“The Man With the Golden Arm”) and John Frankenheimer (“The Manchurian Candidate”) found him a dedicated, brilliant natural actor. But he was known—and feared—by lesser filmmakers as “One-Take Charlie.” He quit “Carousel” when he discovered that two different cameras were to be used and he would have to shoot every scene twice. He would simply walk off a film set and stay away until his demands were met. He insisted on making dopey movies with Dean Martin, Sammy Davis Jr., and Joey Bishop and sometimes cast his consigliere Mickey Rudin in cameos. Nearly his last film, a spoof Western called “Dirty Dingus Magee” (1970), was deservedly a huge bomb.
The sex, however, was reputed to be heroic. Over the years, he took to bed Ava Gardner, Marilyn Monroe, Lana Turner, Judy Garland, Natalie Wood, Lauren Bacall, Peggy Lee, Dinah Shore, Shirley MacLaine, Hope Lange, Angie Dickinson, Jill St. John, Lee Remick, Mia Farrow, Pamela Churchill Hayward (later Harriman), a 15-year-old stripper, the 64-year-old widow of one of his best friends, Zeppo Marx’s wife, and, by Mr. Kaplan’s estimate, hundreds of hat-check and chorus girls and hookers.
He dumped Nancy, the mother of his three children, to marry Gardner but stayed close to her for life. He married Mia Farrow when she was 21 and he was 50—“I’ve got scotch that’s older,” cracked Dean Martin. It wasn’t too long before he and his last wife, Barbara Marx, were sleeping in separate bedrooms. Ava Gardner was the love of his life. Helplessly attracted to each other, they flirted sadistically with reconciliation, but it always ended in tears or worse. When she died at 67 in 1990—33 years after their divorce—he was beyond consolation.
Sinatra’s other great fascination was with the mob. “I would rather be a don for the mafia than president of the United States,” he once confided to the singer Eddie Fisher. He knew many of the godfathers, but he was closest to Sam “Momo” Giancana, the stone-killer head of the Chicago mob. He and Giancana were secret partners in several enterprises, but their bond was sealed when Sinatra introduced the mob boss to Judith Campbell Exner, the complaisant beauty whom he had also shared with the president of the United States, who had also had at least one dalliance with Marilyn Monroe thanks to Sinatra. A half-century later, it is still startling to read about JFK shacking up with a mob moll and a Hollywood goddess—a Norman Mailer fever dream of American decadence—all orchestrated by Francis Albert Sinatra of Hoboken.
A New Deal Democrat, Sinatra worked his way into the Kennedy circle initially through Peter Lawford, who was married to Kennedy’s sister Pat and known to the Rat Pack as “Brother-in-Lawford.” Sinatra’s infiltration of Camelot was complicated by the fact that Jackie Kennedy thought he was a hoodlum and Bobby Kennedy, the attorney general, was on a crusade against the mobbed-up Teamsters union, Giancana and other Sinatra “associates.” But it was the Campbell connection that led to the singer’s banishment when his name and hers kept popping up on FBI wiretaps of the mob boss.
Sinatra, Mr. Kaplan writes, had considered Ronald Reagan a “bozo” since their Hollywood days, but he began migrating to the right after the actor was elected governor of California. He campaigned for Democrat Hubert Humphrey in 1968, but the wary Humphrey camp froze him out, too, and before long Sinatra was hobnobbing with Spiro Agnew and President Richard Nixon. He became a regular at Ronald Reagan’s White House, prompting gossip that he was having an affair with Nancy Reagan. Actually, according to Mr. Kaplan, Sinatra became Mrs. Reagan’s daily phone pal, a confidant as trusted as her astrologer.
After a brief retirement, Sinatra spent his final years performing hundreds of sold-out concerts around the world. He was graced with a marathoner’s stamina, but nearly seven decades of three packs of Camels a day and Jack Daniel’s on demand took their inevitable toll. His memory as ravaged as his body, he died without kin in Cedars-Sinai hospital in Los Angeles—although his wife Barbara later insisted that she had gotten there in time from dinner with friends to hear his last words, either “I can’t” or “I’m losing.”
The magical voice was silenced, but it still reverberates with unmatched vibrancy in American popular culture, a pure gift from a blemished soul.
—Mr. Kosner is the former editor of Newsweek, New York, Esquire and the New York Daily News and the author of a memoir, “It’s News to Me.”