Sinatra: “May I? — it’s your stage, figured I’d ask..”
Dean Martin: “Hey, it’s your world! I’m just livin’ in it.”

(The Rat Pack: Live at the Sands)

In 2010, James Kaplan wrote an eight-hundred page volume about a poor kid from Hoboken, who made it good as a singer, seemed to flame out in the early ’40s, and came back with a bang on the silver screen. The kid who was once floored by punches and got back up is now gone, replace by an increasingly wealthy artist-producer who can seemingly get away with anything, and who will remain an icon for the rest of his life, long after  the Beatles and all that follow take over the pop charts.  If The Voice followed ‘Frankie’ from the gutter to the top, The Chairman  is a chronicle of Sinatra’s use and abuse of his cultural and financial power  as the king of entertainment — for even as his behavior became worse under the influence of constant adulation, his growing wealth and legendary status allowed him to get away with the same behavior that nearly ended young Frankie’s career.  This is not a biography for the reader who merely wants to delight in how cool Sinatra was — there are other books for that —  because the Sinatra here is frequently drunk, ugly, and…well, very un-cool. But Kaplan has produced in these two books a definitive biography,  one that dwells at length on Sinatra’s artistry as well as his relationships with others, and the good and bad flow together.  Although its sheer volume nearly exhausted my considerable interest,  at the end I had to count it worth it.

Artistically, Sinatra seems to have peaked in the 1950s:  after that,  both the changing tastes of the music-buying populace,  and Sinatra’s growing age and iconic status cut his edge. He never ceased to take music seriously, and after initially dismissing Elvis and the Beatles as so much noise, he would listen to them attentively in hopes of figuring out why kids liked them so much, but movies were a different story.  Sinatra’s comeback was based on his outstanding performance in From Here to Eternity, and while there would be a few more stellar roles to come,  after Sinatra gained the wealth and stature to start trying to make his own movies, he would produce films that sold through star power alone.  Sinatra couldn’t lose himself in acting the way he did while singing, and as a result a lot of his later movies have characters who are  just Frank Sinatra with a different name; there’s no suspension of disbelief.  On the set, Sinatra was increasingly disinclined to heed direction, and produced a lot of films that were panned by critics and lukewarmly attended, but  let him pal around with his buddies.   He remained committed to music, however, and the main reason I kept plugging along was for Kaplan’s evaluations of different songs and records; aside from his late Capitol years, when Sinatra was utterly resentful of their refusal to let him go to develop his own label,  Sinatra was a consummate professional about not just singing, but musical performance.  Sinatra didn’t just stand in front of a microphone and sing; he played the mic like an instrument, using it to hide his deficiencies and embellish his strengths.  He also experimented with different musical styles, though he was at his happiest giving performances like those of his youth: the singer and a big band behind him, thrilling now grey-haired bobby soxers.

A major part of The Chairman is Sinatra’s relationships with others, as Kaplan covers his string of wives, his panel of good and lose friends, and his allies and enemies.  Sinatra liked to have a good time, preferring to stay up all night drinking Jack Daniels with his friends, and he was rarely without female company whether or not he was married at the time. (Sinatra definitely got around,  often seeing several women simultaneously, and apparently without an attempt to be secretive.) Sinatra’s serial romances weren’t just about having an interesting dinner companion for the evening;  he was ever restless, always looking for someone who could fill a lonely void.  His frequent heartache, particularly the long-burning torch for his second wife Ava, also informed his music, allowing him to sing songs about lost love like no one else.  He was attracted to power and swagger; throughout his life he’d pal around with members of the Mafia, despite being hauled into court several times to be questioned about mob ties.  Sinatra embodied that swagger himself, and without a powerful person to manage him,  he wasn’t far from acting out if someone angered him.  (He once drove a golf cart through a casino window after they changed owners and stopped his line of credit.)  The lure of power also brought him to DC,  as he sought the friendship of JFK, and would later schmooze with Governor Ronald Reagan and President Nixon despite being a Democrat. Kennedy, whose own lechery was on par with Sinatra’s, was the only person whose fame ever rivaled Sinatra’s, but his wife and brother did their best to keep Sinatra away from  Kennedy.  Kaplan also covers the Rat Pack at length, Sinatra’s clan of buddies who made films with him and who for a while took over Las Vegas with their shenanigans. While filming Ocean’s Eleven, they began disrupting and then taking over each other’s shows, to the point that it didn’t matter who was booked: Sinatra, Martin,  or Davis. They’d all wind up on stage together, drinking and carrying on. The jokes and act grew old after a while,  but in the early sixties nothing like this had been seen before.

The Chairman covers Sinatra’s life at length until the early seventies, when he entered into a “retirement” that was shorter than his marriage to the child-bride Mia Farrow. He came back in less than two years,  and would continue to perform until the 1990s…but this last chapter of  his life is a very small part of the book, and mostly chronicles his friends dying and Sinatra himself growing more tired, until his death in 1998.   Kaplan also includes a touching epilogue about a visit to Sinatra’s grave in Cathedral City,  where the larger-than-life singer rests under a very ordinary marker that will probably be completely sun-bleached in another generation. The music, however, will persist.  There many singers who are descended in chaos  after imbibing too much fame and money,  but what they produce overshadows it: that’s definitely the case with Sinatra.   He was a complex man who could give to charities lavishly, with complete anonymity, and then cause a public scandal — but when I listen to something like “Summer Wind”,   all of the tabloid  bits are blown away.  The voice takes over, and I can only marvel at the story of this poor kid from the wrong side of the river who became an icon — and one whose wealth was produced not through dishonest means, like politics and  crime, but through the sheer joy he brought to people who bought his records.  It’s a heckuva story, and in Kaplan’s version, a heckuva read.

Related:

Frank: The Voice, Jame Kaplan. The first part of this definitive biography, The Voice covers Sinatra’s early rise, fall, and rebound, culminating in his award-winning performance in From Here to Eternity.