Velvet voice and bedroom eyes

His was the voice that defined an idea and a time in American culture. Frank Sinatra was toughness married to vulnerability, edgy elegance, the persona of a fedora-topped scrawny bad boy from the wrong side of the New Jersey railroad tracks who boasted, martini in hand, that he did it all "his way".

But it was transparent from the beginning, from his emergence as a teen idol in 1941, that what Sinatra wanted was what every American boy has always wanted - fame, money, girls, the freedom to do what you damn well please with a minimum of consequence, and a bit later on as maturity begins to take root, respectability. It was that last craving that turned a young singer who might have been dimly recalled as little more than the flavour of a forgotten moment into one of the most enduring icons American culture has produced.

It is no accident that a few years ago the Ford motor company introduced a somewhat pathetic little automobile called Aspire. Aspiration to a higher social class, to acceptance by an elusive Other that somehow seems handsomer and richer and more successful than you is a fundamental American idea. Sadly, allegiance to such an ideal leads often to disappointment - not with failure to gain entrance to the club, but with the unsatisfying nature of successful admittance. When is enough of anything, especially fame and power and money, truly enough?

Sinatra was born in 1915 and grew up in Hoboken, New Jersey. His father was a boxer and his mother was a nurse who played in one of the toughest arenas in New Jersey, Democratic Party street politics. The neighbourhood was tough, mostly ethnic immigrants, and segregated accordingly. The Italians were here, the Jews over there, the Irish down the street. There were no WASPS (White AngloSaxon Protestants); wherever that ruling class lived, Manhattan probably, Park Avenue or some ritzy foreign place like that, it wasn't here. People loved the old neighbourhood, the Italian spaghetti joints and the clam bars, but Hoboken and environs was a place to aspire the hell out of. Young Sinatra was too ambitious and certainly too skinny to follow his father in the boxing ring. But he could sing. At 18 he heard Bing Crosby sing and decided that would be his way to success. By the time he was 24 he was singing with bandleader Harry James for $65 a week. That was a lot of money then, but Sinatra's sights were higher. He soon joined the Tommy Dorsey band, which showcased him as a singer and allowed him to experiment and develop the crooning style that was influenced by the Italian bel canto.

By the early 1940s, Sinatra's velvet voice and bedroom blue eyes were calling a generation to romance. Boys wanted to be him, girls wanted to marry him. Times Square in New York was jammed with hysterical fans trying to score tickets to his appearance at the Paramount Theater. Frank Sinatra, star, had arrived. There were the movies, classics such as Pal Joey and On the Town. There was the 1953 Oscar-winning performance in From Here to Eternity. Of course, and most enduring, there was the music. Sinatra recorded more top 40 albums than anyone, some 51 in all, three more than Elvis Presley. Billboard, the magazine that charts American musical success, says that Sinatra holds an unbeaten record for longevity; some Sinatra song was featured on the top chart every week from 1955 to 1995.

There were the women. The first marriage to teen sweetheart Nancy Barbato lasted 11 years. Three others followed, including liaisons with beauty Ava Gardner and actress Mia Farrow. But also part of Sinatra's resume were his other assignations which were rumoured to include half of the most famous and beautiful women in Hollywood. In a biography of Sinatra, Washington DCbased author Kitty Kelley even claimed that Sinatra had slept with Nancy Reagan. (Mrs Reagan denied the story and Sinatra refused to comment.)

It would have seemed he had it all. What more could he want? The element that dogged Sinatra up to this point in the 1950s was primarily that his career had been sponsored by the underworld. The 1951 Kefauver congressional committee investigating mob infiltration of the entertainment business named him as one of the Mafia's blue chip investments. The Mob was firmly in control of many of the nation's radio stations in those days. Whose music got played and how often were often determined by factors other than quality. That Sinatra was "one of their guys", that his success was assured by their support, was assumed.

Sinatra always denied the allegations. But he was photographed in the company of Chicago mobster Sam Giancana. It was reported that in 1963, when Frank jnr was kidnapped, Giancana offered to provide his own form of justice for the two young men who hatched the caper. His Las Vegas shows were attended by Bugsy Siegel and several tables of men surrounded by bodyguards.

Sinatra became an early fixture in the California resort desert town of Palm Springs when that city was being developed by Moe Dalitz, a man known as the chief of the Jewish Mafia. The problem was that these associations prevented Sinatra from gaining the final thing he wanted: respectability.

In pursuit of the legitimacy that had eluded him, Sinatra sought a kinship with a young Irish senator from Massachusetts named John Kennedy. They had more than a little in common. Beyond a fondness for women and a Catholic upbringing, both men knew what it was like to be kept outside by the ruling class.

The Kennedys may have had money, but they never had the respect of the Boston upper class because, deep down, they were Irish-Catholic immigrants. They became friends, and Sinatra worked hard for Kennedy's presidential election. He raised a great deal of money and there are those who suggest that Sinatra's mob connections may have helped Kennedy's election in certain districts.

His pursuit of what he called "class" cannot be overstated. When Sinatra formed various companies, he always gave them British-style names that he thought sounded "classy". The catalogue record rights, for example, are owned by Bristol Productions. The company that licenses the souvenirs is called Sheffield Enterprises.

And yet it may have been that ultimate respectability that eluded Sinatra. One of the most humiliating moments in his life was said to be shortly after John Kennedy's election. Instead of spending a few days at Sinatra's Palm Springs home, Kennedy elected to stay with Bing Crosby because of Sinatra's association with the mob.

There should have been amends; Sinatra received numerous honours and accolades over the years, both for his generosity and charity and for his enduring talent. His friend Ronald Reagan awarded him the Medal of Freedom in 1985.

But the final elegy Sinatra sought was the Congressional Gold Medal, an award that can only be bestowed by a vote of the entire US Congress. In April 1997 Congress did indeed vote to present the award. All that was awaited was for him to be well enough to attend the ceremony in Washington this spring.

Friends said weeks ago that he was desperately trying to get well enough to travel and receive his medal. In the last few months, Sinatra's travels never got him farther than Cedar-Sinai Medical Centre, a 10-minute drive from his home. He never collected his medal.