Long before his journalism career could take off though, Sinatra discovered that he was a much better singer than writer. First appearing on Major Bowes Amatuer hour in 1935, Sinatra slowly moved toward the music profession. In 1938, he got a job as a singing waiter earning $25 dollars per week but more importantly exposure. After his career was sidetracked first by his arrest for adultery with another man’s wife and second by his marriage to Nancy Barbato only two months later, Sinatra was hired by Harry James to sing in his band. Only six months later, Sinatra switched to the more popular Tommy Dorsey orchestra and his career blossomed from there. On June 7, 1940 Nancy Sandra Sinatra was born while her father was away on tour.

After being named the top band vocalist by Billboard magazine in 1941, Sinatra became larger than the Tommy Dorsey Orchestra. Yet Tommy Dorsey, feeling that he would lose a goldmine, refused to release Sinatra from his contract. This disagreement may have led to a confrontation between Sinatra’s friends in the mob and Tommy Dorsey. This incident, or the rumors that surrounded it, led to Francis Ford Coppola’s “make him an offer he can’t refuse” scene from The Godfather. Whatever Tommy Dorsey’s reasons for letting Sinatra loose, the result was clear: Sinatra was now a solo artist. Over the next three years, Sinatra became celebrity grew enormously. Though he did not get the chance to meet his son at his birth, he was away on tour when Frank Jr. was born, he did meet both President Roosevelt and the Pope. He also met up with exiled mob boss “Lucky” Luciano and many other mob higher-ups including Albert Anastasia. Rumors about his mob connections wore on Sinatra and on April 8, 1947 he attacked newspaper columnist Lee Mortimer for criticizing Sinatra for dealing with the Mafia. But, in the mid forties, life was generally good for Sinatra. He even was present at his second daughter Christina’s birth.

Unfortunately, the good times did not last. During 1949 Sinatra lost his radio program, and his concerts were awful. In 1950, Frank was going through a nasty divorce with his wife Nancy and his infidelity was making headlines nationwide; his film contract was canceled and even his own agent wanted nothing to do with him. In the depths of his depression, he attempted suicide in 1951. Though later that year he married Ava Gardner, they quickly separated and eventually divorced in 1957. Before then, Sinatra had more bad times to go through. Late in 1953, just after the separation, Sinatra’s friends found him attempting to commit suicide again. Then, in late 1954, Sinatra and Joe DiMaggio knocked down the door of an apartment in Los Angeles in which they suspected Marilyn Monroe, DiMaggio's wife, was having a lesbian relationship. After entering, they immediately realized that they had knocked down the wrong door. Over the next several years, Sinatra had many more run-ins with the law; became the leader of the Rat Pack a group of young, swashbuckling,, entertainers; was an instrumental member of John F Kennedy’s election campaign; and married two other women Mia Farrow in 1966, when he was more than twice her age, and Barbara Marx, former wife of the comedian Zeppo Marx, in 1976.

Although he officially retired in 1971, Sinatra performed his last concert in 1994 and died on May 14, 1998 at the age of 82.

Recommended Reading:
The Sinatra Files by Tom and Phil Kuntz
Frank Sinatra: A Celebration by Stan Britt
His Way by Kitty Kelley
The Frank Sinatra Reader edited by Steven Petkov and Leonard Mustazza