“This was the year Frank Sinatra got fat. Not fat, but thicker, more middle-aged,” Kaplan writes in Sinatra: The Chairman, the thoroughly detailed, thoroughly engaging sequel to Sinatra: The Voice. The book is coming, along with an armful of others, on the 100th anniversary of Sinatra’s birth.

The first book ended at the release of the film From Here to Eternity, the movie that marked Sinatra’s comeback, and the rebirth of his career just as he was nearing his 40s. He triumphantly sang “I’ve Got the World on a String." And sure enough he was the marionettist, at least for the next decade. In an instant, he went from being the crooner girls swooned over, to the fighter men emulated; musically, he stopped singing to the women and began singing for the guys.

In The Chairman, Kaplan reminded me of another pivotal moment in Sinatra’s life—when he was heading into midlife. And it got me thinking about my own midlife, as I near 50.

At age 48, while in Hawaii on a film shoot, Frank Sinatra nearly drowned in an undertow rip tide. Saved by a friend, Sinatra had to come to terms not only with his own mortality, but the fact that for the first time he was indebted to someone else.

“Frank’s fury abut his impotence in the waves and his displaced terrors about aging and mortality” caused him to throw a bowl of spaghetti at the man who saved his life; he didn’t like being in a “profoundly uncomfortable position of gratitude.”

Shortly after the drowning episode, Sinatra began filming Von Ryan’s Express, which, like From Here to Eternity, would be another hallmark movie for him. As Kaplan writes, “he was in a full midlife frenzy… a second adolescence.”

It was at this time that he met and fell in love with Mia Farrow. She was a blond, ethereal 19-year-old who partook in the things that Sinatra had despised—she listened to the Beatles, she smoked marijuana and she took LSD.

Yet “Mia was making him feel young and old at the same time.” So what did he do? Rather than rail against the youth culture—Sinatra embraced his midlife. His marriage to Farrow was, not surprisingly, brief; but his music was not. He hit again with a new LP, titled, appropriately The September of My Years.