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Two new portraits depict Sinatra’s charm, loneliness

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Who among us (of a certain age) hasn't been seduced by — or to — the music of Frank Sinatra?

It is an abiding regret that I never saw the man in concert, even if he was no longer in his prime.

After a surfeit of liquor and cigarettes, Sinatra was afflicted by vocal problems. But he kept singing, even tunes (like "Strangers in the Night") that he hated. He was losing his memory, too, as biographer James Kaplan reports in disturbing detail. But for years that didn't stop him. Even near the end, he was still a tough ticket.

This year marks Sinatra's centennial, a celebration replete with musical, film, television, and museum tributes. And, of course, books — of which the crowning glory is surely the second volume of Kaplan's biography, his follow-up to "Frank: The Voice" (2010).


Do not be deterred by the book's heft. "Sinatra: The Chairman" is a riveting read — a juicy, painstakingly researched, excitingly written examination of a brilliant musician, an uneven and temperamental actor, and a charming, erratic, deeply flawed man.

John Brady's "Frank & Ava," which draws heavily on previously published accounts of Sinatra's doomed romance with Ava Gardner, is less essential fare. But it serves as a tantalizing lagniappe for those fascinated by the star-crossed duo — twinned in obsession, emotional instability, infidelity, and, finally, friendship.

The first volume of Kaplan's biography covered Sinatra's New Jersey childhood, his big-band and bobby-sox heartthrob days, his first two marriages, his career doldrums, and, finally, his Oscar-winning turn as Maggio in the 1953 film "From Here to Eternity."

When Kaplan picks up the tale, Sinatra is once again in high demand as both a singer and an actor. He has power, money, and the will to use both. He meets "his musical match," the arranger Nelson Riddle; pals around with mobsters, presidents, and "Rat Pack'' buddies; makes more bad films ("Johnny Concho," "The Pride and the Passion") than good ones ("The Man With the Golden Arm," "The Manchurian Candidate"), and conducts his personal life with impulsive, sometimes violent abandon.


Both his long marriage to his childhood sweetheart, Nancy, and his brief tumultuous one with the gorgeous Gardner have ended, though the two stars would dither over divorcing. (Both ex-wives regarded him as their true love and would remain close to him, Kaplan writes.) Meanwhile, the indefatigable singer would pursue sex with hundreds — perhaps thousands — of women, from cigarette girls to film actresses such as Marilyn Monroe and Lauren Bacall.

The sexual compulsiveness, the drinking, the casino gambling — all were markers of an irredeemably lonely and troubled soul. Kaplan depicts Sinatra as emotionally crippled by his mother, Dolly, and incapable of genuine intimacy. "[A] molten cauldron of oversensitivity and insecurity," Sinatra "had been an adored and abused only child and remained a conflicted Mama's boy," Kaplan writes.

Gallant in courtship, he was generous and loyal in relationships — until he wasn't. He could be cruelly abrupt in his breakups — of friendships (with Riddle, his valet George Jacobs and, for a time, Sammy Davis Jr.), as well as love affairs. His treatment of Bacall, the widow of Sinatra's friend Humphrey Bogart, is particularly chilling. The romance began, Kaplan writes, during Bogart's final illness. It was serious enough that an ambivalent Sinatra eventually proposed marriage. But when news of the engagement leaked, he inaccurately blamed Bacall and, after an angry phone call, cut her out of his life.


Kaplan is a critic of Sinatra's two later marriages. He sees the cultural and generational chasm between Sinatra and "the formidably intelligent" Mia Farrow, nearly 30 years the singer's junior, as insurmountable. Once their ardor cooled, the two principals eventually agreed. (It didn't help that Sinatra insisted that Farrow abandon her film career to cater to him — a demand he also had made of Bacall.) As for Barbara Marx, who stayed married to Sinatra until his death in 1998, Kaplan departs from any pretense of even-handedness and virulently dismisses her as a social climber and worse.

When it comes to Sinatra's musical acumen, Kaplan can be as swooning as any bobby soxer. "Sinatra's genius was to give you the emotion in the moment, to make you feel he was feeling it as you were," Kaplan writes. He was "an alchemist, one who could turn what other artists might leave as dross into gold"; "only Frank was Frank: he was alone at the summit, and he knew it, as did everyone else." There is far more in a similarly adoring vein, as well as a knowledgeable dissection of virtually every album and arrangement, guaranteed to send fans back, once again, to the voice.

Brady's "Frank & Ava" packages its familiar story in a sleek, anecdotal narrative. As Gardner and others have attested in memoirs, and Sinatra underlined in his heart-sore, post-Ava songs, their love was both passionate and impossible to sustain.


Over the decades, they continued to speak regularly, see each other, fall into bed, and even discuss the possibility of remarriage. When she called, Sinatra usually came running. Then, as Brady recounts, one or the other would go storming off — Gardner (who never remarried) to one of her Spanish matadors or costars, Sinatra to another wife or lover.

Long after their divorce, he festooned his homes with her photographs, supported her financially — and even sent thugs to threaten George C. Scott after the actor physically abused her. As for Gardner, she replayed Sinatra's records repeatedly and talked back to them as though the singer himself was in the room.

It's hard not to wonder why this enmeshed duo could never find a permanent safe haven together. Only near the end of his book does Brady venture a hypothesis.

"Each had a need to be free . . . It was the needing each other that they both loved and feared, that held them together and drove them apart," he writes. Finally, he concludes, "they arrived at a deep friendship, . . . sharing the special compassion of two people who, once, long ago, had been in a bad accident together and had survived." It was perhaps the best either of these two damaged souls could manage with anyone.

SINATRA: The Chairman By James Kaplan

Doubleday, 979 pp., illustrated, $35

By John Brady

Thomas Dunne, 292 pp., illustrated, $26.99


Julia M. Klein, a cultural reporter and critic in Philadelphia, is a contributing editor at Columbia Journalism Review and a contributing book critic at the Forward. Follow her on Twitter @JuliaMKlein.