An Appreciation of Frank Sinatra: 1915-1998

Frank Sinatra sang songs about love and longing, about hope and despair, and he communicated the truths of his songs to a mass of strangers as if they were a handful of understanding intimates

June 25, 1998
Frank Sinatra
Frank Sinatra

When the news came, in the late evening of May 14th, that Frank Sinatra had died at age eighty-two of a massive heart attack, it did not come as a shock though it immediately hit as an immense loss. Sinatra had been known to be in seriously failing health for more than two years. What's more, he was a man who had lived a long life and had lived it hard: He drank too much, smoked too long, and raged and wept far too many times as if he could afford all these hazards without risking his grasp on his talent. Apparently, he could. He became a huge pop star in the early 1940s – he was, in fact, American music's first titanic sex sensation – and despite setbacks and his own precarious temperament, he kept both his passion and his prodigy intact for several decades. As the years went along, he became an intense and moving actor, playing complex, tortured characters. He became a friend to presidents, as well as a companion to gangsters. He became an idol to the rich and to the common man alike. And at times he behaved like a vile-tempered thug though one with a reputation for matchless generosity.

For almost sixty years, Frank Sinatra proved to be one of pop music's most abiding paragons – and also one of its most unsettling icons. At the peak of his craft, Sinatra raised the art of romantic singing to a new height, treating each song as if it were the inevitable expression of a personal experience as if there were no separating the singer from the emotion or the meaning of the songs he sang and, therefore, no separating the listener from the experience of a singular and compelling pop voice. But for all the grace of his talent, there was also a substantial darkness about Sinatra: a desperate hunger for the validation that came from love and power, and a damning anger toward anything that challenged or thwarted that validation. In many ways, that fierce need for love and vindication proved the guiding force behind the best moments of Sinatra's career. In the end, his singing amounts to the life testament of a man who learned to cling to one truth above all others  namely, that one could never win love so surely that one could stop imagining the pain of its loss.

Looking at his story, now that it has finished, it makes a certain rueful sense that it was Sinatra's blazing, difficult heart that would finally take his life.

Frank Sinatra Dead at 82

Hsaw fit. In Sinatra's youth she worked as a sometime abortionist and a Hoboken Democratic ward boss, and helped her husband in their saloon, Marty O'Brien's. She adapted herself well to the company that she moved in: She could be eloquent at political gatherings and rough-mouthed and profane among family, friends and enemies  and these same traits also distinguished Sinatra throughout his life. In addition, Dolly doted on Frank – she provided him with nice clothes, a car and cash to entertain his friends. But as John Lahr points out in his superb analytical biography, Sinatra: The Artist and the Man, Dolly also withheld her love and punished her son when he did not match her expectations. This mix of generous reward and stern penalty formed the way in which Sinatra learned how to find love and how to give it, as well, and it became a pattern that he repeated many times in private and public ways.

Frank's parents wanted him to pursue a higher education. In particular, Dolly wanted her son to gain work as a journalist. (When Sinatra's godfather, Frank Garrick, a Hoboken newspaper circulation manager, wouldn't support Frank's attempt to land a sportswriter job, Dolly never forgave Garrick and refused to speak to him again. She later boasted that she was the person who taught Frank to never forget a slight.) Sinatra, though, had ambitions of his own. He longed to leave the delimiting prospects of Hoboken and to cross over the Hudson River to the dream life that might be found in New York. And he thought he had discovered the means to that goal in his parents bar, during the moments in his late childhood when he sang along with the pop songs that played on the music roll of the player piano. Sinatra wanted to be a singer – like his boyhood idol, Bing Crosby  and he developed a fervent belief in his own voice. At first, Dolly disparaged Frank's hope. But when her son's determination outmatched her own, she used her considerable skills to help him. When Sinatra was almost twenty, Dolly persuaded a local trio to take him on as an extra member, and the re-formed ensemble called itself the Hoboken Four. In September 1935, the group appeared on Major Bowes famed radio show, Amateur Hour, with Sinatra on lead vocal, and it was an instant success  though it was Sinatra who, in the months that followed, received most of the attention from audiences. It proved an intoxicating experience for the young singer, as well as a powerful catalyst. As John Lahr and Sinatra's close friend Shirley MacLaine have noted, Sinatra immediately found in an audience what he wished for from his mother: a love that he could coax surely and that he felt he could trust. In some ways, Sinatra's audience became his most significant love, though like nearly all the other loves that mattered to him, it was a relationship that would bring its share of failure, rancor and deep hurt.

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