If Frank Sinatra biographies tend towards the salacious (Kitty Kelley’s His Way) or the scholarly (James Kaplan’s monumental two volumes The Voice and The Chairman), Sinatra and Me: In the Wee Small Hours confirms its distinctive approach by borrowing the title of the singer’s melancholy 1955 album. From 1972 through to Sinatra’s death at the age of 82 on May 14, 1998, Tony Oppedisano was the singer’s friend, road manager and, from the autumn of his years onwards, his “guy” — the person called on to calm the ageing lion roaring in the den of his Palm Springs compound.
Informed by hours of late-night conversations the author had with Sinatra, it’s a bleak tale of fading powers and creeping debility, Rat Pack ring-a-ding replaced by dying fall. The access is remarkable, if unglamorous. At one point Oppedisano is helping a whiskey-tired Sinatra to put on pyjamas when the singer looks down at his penis and sighs. “Madon’, if you could only tell my friend where you’ve been.” “You know, Frank,” Oppedisano replies, “perhaps it would be a shorter list if he told me where he hasn’t been.”
Divided into themed chapters — family, women, friends, the Mob — Sinatra and Me is the work of a genuine Sinatra nerd. It was his knowledge of his hero’s work, after all, that first endeared aspiring singer “Tony O” to the star when they met after hours at Sinatra aide Jilly Rizzo’s legendary New York club. “Who is this kid?” Sinatra demanded as Oppedisano namedropped Sinatra’s long-time guitarist Al Viola, then played How Insensitive. Oppedisano not only claims to have an “uncommon sensory memory”, but also years of preserved calendars, menus, notes of times and places scribbled on napkins or hotel bills. He literally has the receipts.
As mild a narrator though he is, his careful curation gives him some authority to pronounce on notorious Sinatra rumours. No, he does not believe the scurrilous theory that Ronan Farrow, the son of Sinatra’s third wife, Mia Farrow (they divorced in 1968), and Woody Allen, was actually the singer’s child. He has schedules proving that in 1987 Frank’s “emergency diverticulitis surgery” would have hampered his sexual activity around the time of conception.
If, as is often claimed, Sinatra carried $2 million into Havana in his suitcase for the Mob in 1946, it would have weighed “220 pounds — almost twice as much as Frank weighed at the time”. While Sinatra told Oppedisano he never slept with Marilyn Monroe because she was too fragile, he did believe she was murdered — killed with a Nembutal suppository because she knew too much about the Kennedys and the mafia.
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Yet this book isn’t interested in using Sinatra’s position in 20th-century history to spin a murky James Ellroy-like narrative about America. Oppedisano’s gift, instead, is to show the minute textures of Sinatra’s later life — the red pasta sauce and baby-blue pyjamas, the Piaget watches and sudden rages.
The darkness here is more domestic. Sinatra always regretted that he had left his first wife, Nancy Barbato, and their three children, for Ava Gardner; more than once, he asked the author to drive him over to Nancy, losing his nerve before he asked to be taken back. The rift between his fourth wife, Barbara Marx, and his first family was profound — Barbara was convinced her stepchildren would encourage Sinatra to act against her.
The man once nicknamed Leader seems to have little agency here: when Barbara decides to sell his beloved Palm Springs compound, he is bewildered by all the little dots appearing overnight on his possessions. It fell to Oppedisano to explain that Barbara was shipping them off for auction. Even at Sinatra’s funeral, hostility spilt over the pews, Barbara and Sinatra’s youngest daughter, Tina, tussling over the memorial crucifixes handed out to mourners by the priests.
Yet Oppedisano isn’t interested in unseemly wrangling for prominence here: you sense he has always known his place in Sinatra’s world — an observer, a caretaker, loyal to the point he was holding Sinatra’s hand when he died.
Occasionally indulgent and sentimental, his account still adds a tenderness and vulnerability to Sinatra’s story that’s there in his music, but rarely in his biography — an intimate study of a man in decline, a man alone.
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Sinatra and Me: In the Wee Small Hours by Tony Oppedisano with Mary Jane Ross
Scribner £18.99 pp320
