Song = "My Way"
"Ol' Blue Eyes" transformed popular songs from crooning sentimentality to ageless classics by injecting personal feelings and intimacy and using his innate professional style and polish.
Born in Hoboken, New Jersey - a down-at-heel suburb of New York - the son of Italian immigrants he started as a singing waiter but by his 20s was performing with his hero Bing Crosby.
Turned "crooning" into an art-form
Sinatra, whose mother was a well-known fundraiser and organiser for the New York City Democrats, established himself as a front man during World War II.
Having learnt to breathe in time with the music, from band leader Tommy Dorsey, he turned "crooning" into an artform. He was the first star to have young girls swooning at his feet.
Some 20 years before Beatlemania, Sinatra's rakish look drove screaming crowds of bobby sox-wearing girls wild.
He moved into films but had to fight hard to win his role in From Here To Eternity (1953), in which he starred alongside Burt Lancaster and Montgomery Clift.
Oscar winner
Sinatra played Maggio, a cocky, streetwise Italian-American soldier who is beaten to death by the villainous Ernest Borgnine.
He won an Oscar for Best Supporting Actor and later won critical acclaim for his performance in The Manchurian Candidate (1962).
In the 1950s he formed the original "Brat Pack" with Dean Martin and Sammy Davis Jr and spent his time jetting between Las Vegas, Los Angeles and New York's Copacabana club.
Sinatra appeared in dozens of films, one of the most notable of which was the hit musical Guys and Dolls (1955) in which he co-starred with Marlon Brando.
More urbane style
As Sinatra got older and his waistline grew, his audience changed and so did his performance.
Crooning gave way to a more urbane style and he began to tackle more difficult work.
In the 1960s Sinatra's super-clean image was muddied by allegations of mafia links.
A photograph of him with mafia chiefs was shown to the Nevada Gaming Board and, although he insisted he had only ever met them at social functions, he was refused a gaming licence.
Personal friend of the Reagans
He later gained a licence but mafia allegations continued to dog the rest of his career.
Sinatra, born into a staunchly Democrat household and a one-time friend and supporter of the Kennedys, became a Republican fundraiser in the late 1970s and became a personal friend of President Ronald Reagan and his wife Nancy.
In 1987 author Kitty Kelley "exposed" Sinatra's mob ties in an unauthorised biography in which she claimed he had used mafia muscle on a number of occasions to further his career.
But the persistent rumours failed to tarnish Sinatra's popularity and chat show hosts, journalists and promoters continued to beat a path to his door.
Song-writers loved working for him
Despite several concerts being billed as his farewell performance Ol Blue Eyey seemed unable to give up the thrill of live performances or the search for ballads to turn into what he called polite jazz.
Above all, Frank Sinatra knew how to master the lyrics of a song and song-writers loved working for him.
His way was to hang behind the beat, jazz up the phrasing - anything to let the words of the song tell their story.
Sinatra married four times. His first wife Nancy Barbato, his teenage sweetheart, bore him three children.
After 13 years of marriage he left her and in 1951 wed Ava Gardner, one of Hollywood's biggest stars.
The marriage did not last and in 1966 he got hitched to a young actress called Mia Farrow - another relationship that was doomed.
She was 21 at the time and he was 51. The marriage lasted 18 months.
In 1976 he took the plunge once more, marrying Barbara Marx.
In his last years Sinatra retired to his palatial home in California where Barbara and his children Tina, Nancy and Frank Jr formed a protective shield around him.
He suffered a mild heart attack in January 1997 and his health was in decline ever since.