Behind Blue Eyes: James Kaplan’s Sinatra: The Chairman

A remarkable and wide-ranging study of Frank Sinatra’s second act.

It would be easy to label Kaplan’s massive two-volume biography of Frank Sinatra—this second volume checks in at 992 pages, following the 786-page first installment, Frank: The Voice (2010)—as an example of massive overkill, but such an assessment would miss the mark entirely. This is not one of those documentary-style biographies in which the fawning author records what his subject had for breakfast every day of his or her life; rather, it is a remarkably insightful, gracefully, often eloquently written history of popular music and celebrity culture in twentieth-century America—all viewed through the lens of an iconic singer and undervalued actor whose wildly contradictory personality and tempestuous personal life built the legend but detracted from the man’s genius as an artist.

Sinatra The Chairman

Sinatra: The Chairman. By James Kaplan. Nov. 2015. 992p. illus. Doubleday, $35 (9780385535397); e-book (9780385535403). 782.42164092.

It really was a two-act life, and Kaplan divides his volumes perfectly, ending the opening act with Sinatra’s Supporting Actor Oscar for From Here to Eternity in 1954, and following in the second act with the story of Sinatra as Chairman of the Board, an alternately triumphant and tragic account of sublime artistic achievement, grossly excessive displays of arrogance, and, inevitably, personal and professional decline. Yes, these were the years of the Rat Pack, and Kaplan nicely separates the truth from the legend, reminding us that there were really two Packs, the first, led by Bogie and Bacall, with Sinatra as a mere member, and the second, the Frank-Dino-Sammy version, the “ring-a ding-ding” years that went on far too long, eventually becoming an offensive minstrel show, but that, in the beginning, “embodied Hollywood’s most elemental myth, its deepest unspoken appeal—that as its final reward, fame offered a life without rules.”

And, yes, these were the Vegas years and the Mob years, where Sinatra arrogantly denied his association with all variety of Mafioso, Sam Giancana at the forefront. Again, Kaplan carefully sorts through the evidence—mountains of it—and concludes convincingly that while Frank was no mobster, he loved to be around them, basking in the power they exuded.

Sinatra’s second act, Kaplan emphasizes, is a study in the use and misuse of power—and it wasn’t all misuse. Showing terrific chops as a music critic, Kaplan offers an in-depth appreciation of Sinatra’s wonderful Capitol years and his collaboration with arranger Nelson Riddle. Drawing on interviews with those who were in the recording studio, Kaplan shows in vivid detail how Sinatra used his unrivaled clout as a star to produce a series of albums that redefined what popular music could be. “Concept albums” like Only the Lonely and Songs for Swingin’ Lovers! displayed the potential of a relatively new technology, the long-playing record. The records weren’t just a smash with would-be swingin’ lovers; hipsters were listening, too. Sinatra always saw himself as a jazz singer, and so did the great jazzmen of the day, including Lester “Prez” Young, who said simply, “My main man is Frank Sinatra.” Kaplan perfectly sums up this tribute with the words, “No one was hipper than Prez, and no praise could be higher.”

As astute in his psychological analysis as in his music criticism,
Kaplan makes sense of the singer’s insistence on taking
way too many encores.

Fortunately, Prez wasn’t around for Sinatra’s sad coda, the tours at the end where his voice was mostly gone and he couldn’t remember lyrics. As astute in his psychological analysis as in his music criticism, Kaplan makes sense of the singer’s insistence on taking way too many encores by noting Sinatra’s need for constant movement: “He was like a whole body case of restless leg syndrome.” That restlessness finally shook itself out, but, along the way, it drove a skinny kid from Hoboken to live a life that, as Kaplan concludes, “touched almost every aspect of American culture in the twentieth century.” That’s a big statement, but this big book makes us believe it.

This review first appeared in the November 1, 2015, issue of Booklist.




About the Author:

After more than 30 years at Booklist, editor and publisher Bill Ott continues to edit the crime fiction section of the magazine and still delights in discovering new hard-boiled writers. Follow him on Twitter at @Booklist_Bill.

1 Comment on "Behind Blue Eyes: James Kaplan’s Sinatra: The Chairman"

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  1.' Rob J says:

    The first volume was magnificent, one of the best I have ever.
    I look forward to reading the second part with enormous anticipation.

    FS had a true manic-depressive personality, the extreme highs and lows
    of his life emerged in his art. One has “Songs For Swingin’ Lovers”
    as a major high, and then there is “Only The Lonely” which is one
    of the bleakest records ever. It speaks volumes FS named the latter
    as as a personal favourite. Interestingly enough,his family hated
    “Only The Lonely”.

    Ultimately, how many of us would behave in the same way, if we had
    unimaginable success ? Probably not that much different from FS, sans Mob associations.

    Just look at the behaviour of Charlie Sheen….

    The real sorrow is that FS went on for too long, as opposed to leaving at the peak of his powers. Regardless, it promises to be a
    a brilliant book.

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