Few, outside of classical music circles, would quibble. “He loved, he brawled, he had style, he had guts, he could even act,” Bruce Handy wrote in his profile of the boy from Hoboken. “And, oh yeah, he defined American pop.”
Much has been written of Sinatra’s unassailable greatness as a singer, and most of it is justified. His musical idol was Bing Crosby, and James Kaplan Crosby’s influence on Sinatra cannot be underestimated.
“The period of Bing’s explosion into the American consciousness, propelled by radio’s beginnings as a truly mass phenomenon, precisely coincided with Frank Sinatra’s emergence as a sexual being. There he was alone in his room, just him and his radio — and that voice coming out of it.”
The thrill he felt at the sound of Crosby’s voice was couched in the certainty that the voice was speaking to him alone. “In fact, in the case of Crosby and Sinatra, genius was speaking to genius — though in Frank’s case, the genius was very much nascent. Frank Sinatra was a slow bloomer.”
Slow or not, by the age of 23, Sinatra had a plan. “He was going to knock over Crosby. He knew it in the pit of his gut.” This was an early sign of the hubris that would contribute to his greatness as a singer, but also make him obnoxious and utterly insensitive to the feelings of others as a person.
Kaplan, a novelist and journalist who co-wrote John McEnroe’s international bestselling autobiography Serious, reminds us that Frank was always obsessive about success. “Sinatra was gigantically ambitious; virtually every move he made in his life had to do with the furtherance of his career.”
Along with ambition, he was ruthless. “The story of Frank Sinatra’s life is one of continual shedding, both of artistic identities and of associates and intimates who had outlived their usefulness.” Women, in particular, were sometimes brutally treated by the man who was one of the greatest ever purveyors of romance through the magic of his music.
And then there was the Mob. “His connections to gangsters should be neither overemphasised nor underplayed,” according to Kaplan. “As many entertainers who came up in the great era of nightclubs (the 1930s through the early 1960s) have pointed out, it was impossible to play the clubs and not come into contact with the Mob
“Organised crime during Frank Sinatra’s early career, and prior to the US government’s tardy but assiduous attempts to break it up, was a vast darkly shimmering American under-culture — an alternative economy so huge that the über-criminal Meyer Lansky was able to boast, famously, ‘We’re bigger than General Motors’.”
Sinatra’s daughter, Tina, in her own book about her father, put it simply: “You couldn’t get gigs in places like Las Vegas and Reno without dealing with the Mob when my father was starting out. That didn’t mean he was one of them or even admired them”.
Yet the very young Sinatra, who grew up in an area that was “mobbed up”, was somewhat in awe of gangsters and the swaggering way they comported themselves. “He both wanted to be one of them and — in spirit and in part — really was,” writes Kaplan.
The singer’s infatuation with and pursuit of Ava Gardner not only ruined his marriage to Nancy, but nearly put the kibosh on his career. By 1947 that career had already taken a nosedive. Various factors contributed to this. Sinatra had for a time lost his way as a singer; his standing in Hollywood was low following a number of movies that bombed at the box office, and his public reputation had been seriously shredded by a number of newspaper columnists, mainly working for the Hearst newspaper group.
At the end of World War II, he stood accused of being a draft dodger (but then so was John Wayne, but nothing was ever said about that). His Mob connections gave ample ammunition to his enemies, and the FBI director J Edgar Hoover was convinced Sinatra was a Communist.
This latter assertion was, of course, laughable, though it wasn’t one bit funny in the context of the post-war “Reds-under-the-bed” paranoia that swept the States, and more than one showbiz career was destroyed during the McCarthyite period (1950-54).
Sinatra was certainly a liberal in those days; he never sought to hide his admiration for President Franklin Roosevelt and his New Deal, and he brought opprobrium on himself from the right-wing press by insisting on working with black entertainers such as Sammy Davis Jr. He canvassed for JFK during the latter’s race with Richard Nixon for the White House in 1960, though 20 years later he switched sides and backed Ronald Reagan for President.
It’s also worth noting that when Sinead O’Connor famously tore up a photograph of Pope John Paul II on national television in the USA in 1992, the once very unconventional Sinatra (born into an Italian Catholic family) publicly rebuked her and said he would like to “kick her butt”.
With his career on the slide, and money running out, the last thing he needed was a major distraction, and that came in the shape of the beautiful Miss Gardner. From the outset theirs was a tempestuous affair. Kaplan sums it up: “The reality is that their relationship was impossible by definition. They were competitors as well as lovers”.
Composer Jimmy van Heusen recalled that when Sinatra came to stay with him in New York at time when the marriage was in deep trouble, the singer caused havoc. “Ava! Ava! Ava! He’s driving me crazy. A billion f*****g broads in the world, and he’s got to pick the one that can take him or leave him”.
Kaplan also relates the story of a blazing row between the two lovers, during which Ava ordered Frank out of the house. “Okay, okay, I’m leaving. And if you want to know where I am, I’m in Palm Beach f*****g Lana Turner!”
The blonde star of The Postman Always Rings Twice was one of his long-time lovers, along with a lesser known actress named Marilyn Maxwell. In between there was a host of other starlets, cocktail waitresses, air hostesses and prostitutes, especially black hookers. It seems that he developed a particular taste after an experience with a Billie Holiday lookalike (he always claimed Ms Holiday as a musical influence).
As for those who wondered how the skinny Sinatra could be such a hit with so many women, the answer in part came from none other than Ava Gardner. Acknowledging his puny size, she said: “There’s only ten pounds of Frank, but there’s a hundred and ten pounds of cock”.
Years later, in the twilight of his amazing career, he tried to downplay his prowess with women. “If I had as many love affairs as you’ve given me credit for,” he told reporters, “I’d now be speaking to you from a glass jar in Harvard Medical School”. This though, writes Kaplan was an evasion. “No, it was more than an evasion, it was the Big Lie.”
Two things really saved Sinatra — the 1953 movie From Here to Eternity (for which he won the Best Supporting Actor Oscar) and a chance encounter with a genius of an arranger named Nelson Riddle. If his role as Maggio was his redemption in the eyes of Hollywood, his association with Riddle brought about his musical redemption.
“It was the greatest career comeback ever,” the columnist Louella Parsons wrote later. And that’s where Kaplan ends this fascinating biography — the night of the Academy Awards at the Pantages Theatre, Hollywood, March 25, 1954.