Fifty pages from the end of “Sinatra: The Chairman,” the second and concluding volume of James Kaplan’s magisterial biography of Frank Sinatra, I guarantee you’ll begin to weep. Not because you’ve finished a 900-plus-page book (though you will feel relief), or because Kaplan so persistently details the ugly truth about Sinatra: his bullying, perhaps murderous personality; his whoring; his inability to say “sorry”; his pimping for JFK, whom he called “Chickie Baby”; his mob connections; his penchant for breaking furniture and throwing spaghetti at his valet; his mind-boggling error in marrying Mia Farrow and making any number of bad records. No, you will weep over the death of a massive and unforgettable talent whose style of living helped define postwar America, and you will weep for an America that no longer exists, whether you lived during those years or just yearn for their return. Good luck, pal, they’re gone.

To control this massiveness, Kaplan orders his details chronologically, alternating between biographical information, musical accomplishments, wives and girlfriends, and involvement with the Mafia. The adhesive between these divisions is quotations from contemporary gossip sheets, news articles and interviews. The overall effect is the inseparableness of the man and the legend, and an extended demonstration of how celebrity culture became embedded in every aspect of our society, from how we wore our hats to how we glamorize corruption. Unfortunately, prolonged reading can lead to information overload, but stick with it because you’ll learn a lot.

Volume 2 begins with Sinatra’s comeback, his Academy Award-winning portrayal of Pvt. Angelo Maggio in 1953’s “From Here to Eternity.” No longer “pilloried” for his affair with Ava Gardner or his failure to serve in World War II, Sinatra began his steady climb to “new heights of arrogance.” The great recordings he did with Capitol had begun, and Hollywood and Las Vegas awaited. Sinatra had always been “like a whole-body case of restless leg syndrome,” working (and drinking) till dawn, insisting on only one take for movie shots, and controlling his recording sessions with his ruthless talent and by ruthlessly disposing of arrangers and songwriters when he got tired of them. Songwriter Jimmy Van Heusen, a longtime friend, referred to Sinatra behind his back as a “monster,” but he stayed with him “because he sings my songs.”

Sinatra was the ultimate swanky tough guy. With his harem, his daily bottle of Jack Daniel’s, his unfiltered Camels, his beefy bodyguards, his impeccable and sometimes flashy clothes (his favorite color was orange), he embodied the paradox of 20th-century masculinity: a hard shell held in place by fear of humiliation. Lyricist Sammy Cahn said, “There isn’t any ‘real’ Sinatra. There’s only what you see. You might as well try to analyze electricity. . . . There’s nothing inside him. He puts out so terrifically that nothing can accumulate inside.”

Cahn was wrong. Inside Sinatra was his voice, one that communicated the vulnerabilities and loneliness of the American male. His famous fedoras may have hidden his fading hairline, but when he sang, he was naked.


Sinatra needed to be constantly loved, hated to be alone and didn’t like to be touched, a troika of insecurities that probably began with his mother, Dolly, who coddled him when she wasn’t beating him, throwing him down the steps or holding his head under the ocean waves. But for every guy he socked in the nose, every hotel room destroyed, every crude remark hurled from the stage, his generosity was as big as his voice. Kaplan writes, “There was Daytime Frank, and there was Nighttime Frank,” meaning he was an unmedicated manic-depressive: easy to love, easy to hate and impossible to dismiss.

The end was slow and inescapable. First there was rock-and-roll, which Sinatra characterized as “brutal, ugly, degenerate [and] vicious.” Then the Beatles pushed him off the charts. Then polarizing political upheavals caused him to change from a New Deal Democrat to a Spiro Agnew-loving Republican. We can include his grab for youth via his marriage to Farrow in 1966 , the Nehru jackets and love beads, and Howard Hughes buying the Sands hotel, “the birthplace and playground of [Sinatra’s] Rat Pack.” In 1996, when Sheldon Adelson demolished the hotel, Sinatra knew the world he helped create was finally dismantled, pushed aside by the youth movement and new ways of doing business.

Despite announcing his retirement in 1971, Sinatra recorded a new album, “Ol’ Blue Eyes Is Back” in 1973. According to Kaplan, this is the first time anyone had called him Ol’ Blue Eyes. And he kept touring, despite failing health. In March 1994, he collapsed on stage in Richmond and again a few months later in Atlantic City. His final performance was in Palm Desert, Calif., on Feb. 25, 1995, a concert that concluded with the song “The Best Is Yet to Come.”

David Lehman’s “Sinatra’s Century” is a much shorter but more intimate portrait. Many of the same anecdotes used by Kaplan can be found here, too, but Lehman, an established poet, widens the frame of reference, thereby expanding the emotional resonance of the songs. He compares Sinatra’s version of “One for My Baby” to both Humphrey Bogart in “Casablanca” and to Ernest Hemingway’s famous story “A Clean, Well-Lighted Place.” Whereas Kaplan accumulates facts, Lehman tells us what those facts mean. For example:

“There are two reasons that male resistance to Sinatra turned completely around. . . . His voice deepened . . . and he was able to sing so convincingly of loss, failure, and despair unto death.” But when a fact is needed, Lehman comes through: In a 2014 commercial for Jack Daniel’s, a voice-over tells us what Sinatra’s recipe was: “three rocks, two fingers, and a splash.”

There it is, a Sinatra haiku, and, boy, what a splash he made.

Sibbie O’Sullivan is a writer on the arts who lives in Wheaton.

The Chairman

By James Kaplan

Doubleday. 979 pp. $35

One Hundred Notes On The Man and His World

By David Lehman

Harper. 268 pp. $24.99