On Jan. 20, 2021, only the most die-hard fans of President Donald Trump tuned in to watch the outgoing chief executive’s farewell address from Joint Base Andrews in Maryland, but those who did will surely remember the coup de theatre with which it ended: As Air Force One whisked Trump & Co. away to Mar-a-Lago, speakers boomed a recording of Frank Sinatra singing “My Way.”
Perhaps the song was intended as an unapologetic ode to Trump’s governing style. Maybe it was nothing more than a reflection of the former president’s inimitable musical tastes. But deeper meanings suggested themselves. One wondered, in the pairing of Sinatra’s song with the image of the plane disappearing into the horizon, whether one was watching the sunset of a certain kind of go-it-alone manliness, the sort typified by these two brash, hard-charging New Yorkers.
One wondered, too, whether the public, ever more hypersensitive and politically correct, still has an appetite for the prideful, red-blooded chest-thumping of Ol’ Blue Eyes. Outside of baby boomers such as Trump, wannabee Rat Packers, and self-conscious nostalgists, do people really still listen unironically to such macho ballads as “My Way” or “New York, New York”?
The latest addition to the Sinatra bookshelf, Sinatra and Me: In the Wee Small Hours, a memoir by the entertainer’s longtime road manager and pal, Tony Oppedisano, does not exactly make a case for Sinatra’s continued relevance. Oppedisano doesn’t only write from the perspective of an insider; he plainly, unapologetically, worships Sinatra.
Indeed, the book adopts a devotional tone about its subject. To read this book, Sinatra loved all the women in his life, but retained an extra special feeling for his first, the mother of his three children, Nancy Sr. He loved not only his own children but also children he did not know, especially at Christmastime, when their gifts might have been stolen by thieves and Sinatra served as an ersatz Santa Claus. He was a swell guy to have as a friend, and if he played a prank on you, it was only to show how much he loved you. He had a temper, of course, but Oppedisano was never, ever on the receiving end of it.
All the same, Oppedisano’s engagingly intimate portrait goes some way toward humanizing a figure who has become calcified in the popular imagination, forever holding drink and cigarette in hand (as he is in the picture on the dust jacket of In the Wee Small Hours, the title of which is borrowed from what is arguably Sinatra’s greatest album, a hauntingly stoic portrait of nighttime loneliness).
In December 1971, Oppedisano, then a 21-year-old aspiring musician, was first introduced to his idol, who was about to turn 57. The age difference was never the barrier, though. Their personal backgrounds were simpatico — both were working-class Italian-Americans — and their friendship was surely sustained by the younger man’s open worship of the elder. What big star doesn’t love a groupie?
Nonetheless, not wishing to be perceived as a “hanger-on, looking for favors,” Oppedisano labored for years on what proved to be an unsuccessful performing career. Then, with the death of Sinatra’s previous road manager, Jilly Rizzo, in 1992, Ol’ Blue Eyes finally turned to his mentee: “I think it would be a good idea if we start spending a lot more time together because I’m going to need you, and you may need me.” In Sinatra-speak, that constituted a job offer, and Oppedisano served as his friend’s right-hand-man until his death in 1998 at age 82.
The conceit of the book is that many of its anecdotes derive from Oppedisano’s countless informal tête-à-têtes with Sinatra, whose take on the joys, scandals, and disappointments of his life are given the authority of gospel. Many are well trod but told with freshness and verve. Born in Hoboken, New Jersey, to a fireman named Martin and his wife Dolly, Francis Albert Sinatra was called “Slacksie” for his early affinity for dressing to the nines. “The guys used to tease him that they could cut their finger on the crease in his pants,” Oppedisano writes.
Sinatra is given the last word on the uncomfortable relationship between his fourth wife, Barbara, and his daughters with Nancy Sr., Nancy Jr. and Tina. Reflecting on a visit with his first wife, grown daughters, and grandchildren, Frank told Tony, wistfully, “I just had a glimpse of what my life could have been. You do realize it’s going to take me months to get over it now?”
Oppedisano expends considerable ink rebutting Sinatra’s purported association with (though not his rubbing shoulders with) members of the mafia, though Frank’s own witticisms summarize things nicely: “Frank loved to joke that the initials FBI stood for ‘Forever Bothering Italians.’”
Oppedisano also aims to debunk decisively the rumor that Sinatra, not Woody Allen, fathered the son of his ex-wife Mia Farrow, journalist Ronan Farrow, by providing a painfully detailed account of his boss’s whereabouts at the time when Ronan would have been conceived. Oppedisano is on less lurid ground when discussing his conversations with Sinatra about his philosophy of vocalizing. “In normal conversation, you don’t run out of air until you’ve completed your thought, even though you don’t know what you’re going to say until a split second before it comes out of your mouth,” Frank told Tony. “Why wouldn’t you do the same thing in singing?”
The book is littered with mock tough-guy jargon that alternately grates and amuses. “He might say yes in a New York minute to a good-looking girl looking for love, but he put the brakes on if sex would be damaging to her,” writes Oppedisano, who later describes, in prose redolent of Guys and Dolls, Jacqueline Kennedy Onassis as “very pretty, very classy.” The author has a serious propensity for clichés: “Frank could be extraordinarily generous with his fans;” “Being thanked or praised for helping someone made Frank really uncomfortable;” and “Frank Sinatra was a dyed-in-the-wool patriot.”
But despite the book’s grandiosity and insularity, the picture that emerges here is largely believable and mostly lovable. Sinatra’s tough exterior, sensitive inner life, abundant generosity, and gift for firm friendship come through. In fact, those attributes look pretty good today — as they did back in January, when the ex-president summoned Ol’ Blue Eyes to say so long.
Peter Tonguette writes for many publications, including the Wall Street Journal, National Review, and the American Conservative.
