Frank Sinatra

The Voice. The Sultan of Swoon. The Chairman of the Board. Old Blue Eyes. The Greatest Singer of the Popular Song.

The provider, according to Gore Vidal, of the background music that was playing when half of North America’s population was conceived. A notorious bachelor and a family man. A lover and a fighter. Francis Albert Sinatra.

Upon his entry into the world, Sinatra was thought to be stillborn until his grandmother doused him with cold water – probably the first and last time his vitality would ever be in question.

His temper, sure, that was questioned – his high-profile friendships with high-profile men, his luck with the ladies, his health at the end – all of these were questioned. But never, never his vitality.

Descriptions of Francis’ Italian immigrant parents definitely speak to the man their boy would become.

His father was a boxer and a fireman who thought singing was for sissies. His mother, Dolly, was a former saloonkeeper who sang at their family and community gatherings and flying in the face of her husband’s “sissy” ideas, she paid for Francis’ singing lessons.

In high school in 1933, Sinatra saw his hero Bing Crosby at a concert and vowed that he too would become a crooner someday (always one for an audacious boast, he also vowed that he’d be more successful than his hero).

Between local jobs, like a runner/sportswriter gig for The Jersey Observer, Frank sang with a neighbourhood vocal outfit called The Hoboken Four, and the group won their share of amateur talent contests around town – ten bucks or a set of dishes was their frequent prize.

His first professional job came as the singing waiter/emcee at the Rustic Cabin, a roadhouse eatery in Englewood Cliffs, NJ. Trumpet player Harry James, who had played in Benny Goodman’s band, heard Sinatra one night and hired him to sing in the band he was assembling.

Seven months later, James let Sinatra out of his two-year contract so the skinny crooner could join trombonist Tommy Dorsey’s swing band.

From 1940 to 1942, the band would frequently hit the Top 10. Their hits included Imagination, Polka Dots and Moonbeams, Fools Rush In, The One I Love, In the Blue of Evening, Violets For Your Furs and I’ll Never Smile Again, which went to number one.

Dorsey and his line-up appeared in several films during these years, so via a handful of cameos as the singer, Sinatra made his fateful introduction to the silver screen.

Maybe more important than all this, however, was the breath control and the art of delicate phrasing that Sinatra learned from his bandleader boss. Sixteen bars and nary an inhale – No problem.

In late 1942, The Voice went solo. Dorsey wasn’t as easy-going as Harry James had been about letting the crooner out of his contracts – he demanded, and got, a chunk of Sinatra’s future profits for many years. But Frank was a quick solo smash, so giving up the cash was worth it.

Because he was exempt from fighting in the war thanks to a damaged eardrum, he became a veritable singing institution in the mid-40s. He sang for Benny Goodman’s band and starred in the popular radio show Lucky Strike Hit Parade.

His trademark romantic baritone made the ladies miss their soldier beaus overseas, and it made the younger girls shriek – he was such a teeny-bopper idol, in fact, that when he was trying to refine his image a few years later, he actually had to ban the banshee under-agers from his radio broadcast tapings.

Signature tunes like When Your Lover is Gone, The Song is You and I’ve Got a Crush On You became a part of his repertoire. But in 1946, he signed a five-year contract with MGM and put his singing career on the back burner so that he could devote himself to acting.

During the early 1950s, Sinatra’s music and acting career dried up – a drought helped along by his rocky relationship with Ava Gardner (and ‘rocky,’ according to Sinatra legend, is a very understated adjective), his divorce from first wife Nancy, a load of bad press, haemorrhaged vocal cords, and his talent agency and movie studio turning their fair-weather backs.

But an Academy Award-winning performance in From Here to Eternity (1953) marked his comeback to the screen, and he would soon step back into the recording studio as well.

Sinatra left the Columbia label in 1953 and moved to Capitol, and now, instead of his patented lovey-dovey ballads, Sinatra veered in a bolder, more sophisticatedly swinging and jazz-influenced direction.

He teamed up with arranger Nelson Riddle, whose work with Nat King Cole had impressed him, and recorded hits like (the supposedly Ava Garner-inspired) My One and Only Love, My Funny Valentine and Young at Heart.

He would also work famously with Billy May and Gordon Perkins. Albums, not singles, were the emphasis, but of course, there were plenty of the latter – Young at Heart, Learnin’ the Blues, Hey! Jealous Lover, All the Way and Witchcraft among them. He was no ingénue anymore – his slightly deeper voice seemed worn with a few Ava battle scars – but it was just as rich as ever.

In February 1960, Frank and the Rat Pack – Sammy Davis Jr, Dean Martin, Peter Lawford, Joey Bishop, and Sinatra himself – entertained senator John F “Jack” Kennedy (Lawford’s brother-in-law) in Vegas.

A mutual respect was established. JFK envied Frank’s Rat Pack lifestyle, and Frank envied Jack’s power. The Sands’ invisible owners donated a million-dollar cash-in-a-suitcase gift, and Kennedy struck up a relationship with one of SInatra’s on-off squeezes and good-time-girls, Judy Campbell. It was the beginning of a two-year affair between Kennedy and the girl.

Frank would also introduce Campbell to another friend, a short, balding guy in a sharkskin suit, silk shirt, and alligator shoes called Sam Flood, aka Sam “Momo” Giancana, head honcho with the Chicago Mafia. Sinatra and Giancana had known each other since the 1950s when Frank would play Catholic charity benefits in Chicago.

Sinatra left Capitol – telling Capitol president Alan Livingston, “Fuck you and fuck your building, I’m gonna tear it down, and I’ll do everything I can to ruin you” – and created his own record label, Reprise (as in “reprisal”), saying, “I want to avoid having bad rock & roll records associated with Reprise, and the policy in the main will be to concentrate on quality performers”.

His first few Reprise efforts faired tolerably, but his real comeback triumph came in 1965 when he headlined the Newport Jazz Festival, accompanied by Count Basie’s orchestra and conducted by Quincy Jones. Strangers in the Night spent 73 weeks near the top of the charts, its title song going to number one.

His duet with daughter Nancy the following year, called Something Stupid, also went to the top. The rest of the sixties unfolded under bright lights – either up on the big screen or onstage in Las Vegas, where he was a main attraction for years.

At the decade’s close, Sinatra recorded My Way, based on a French song Paul Anka had adapted to the English language. The single did just fine in the States, but it stayed at the top of the UK charts for an unheard-of 122 weeks.

And as if all of this weren’t enough for the fella who kept big band alive in the decade that saw the dawn of the hippies, Sinatra also made acclaimed forays into the Brazilian world of bossa nova, with Antonio Carlos Jobim guiding the way.

Sinatra announced his retirement in 1970 – his first retirement, anyway. He was back three years later with TV specials and a Nixon White House appearance and toured sporadically but successfully thereafter.

In terms of record releases, the crooner remained quiet in the mid-70s, but in the mid-80s, he released Trilogy, which included the most well-known version of his Big Apple homage, New York, New York.

The 90s saw the release of Duets I & II, which included just that – Old Blue Eyes sharing the mike with the likes of Aretha Franklin, Bono from U2, Tony Bennett, Liza Minnelli, Luther Vandross, Chrissie Hynde from The Pretenders, Linda Ronstadt, Willie Nelson, Patti LaBelle and Lena Horne. He also added two more Grammies to his collection.

Sinatra sang well into his late 70s. The shrieking bobbysox girls were all grown-up but just as devoted as ever, and he charmed his way into younger generations’ hearts as well. That old-school Las Vegas has become a retro golden age . . . the Rat Packers are its icons; Sinatra’s combination of tough guy and wearer of heart on sleeves is its standard of masculinity.

But on his 80th birthday, New York City lit up the Empire State Building with blue lights. Las Vegas wasn’t the only electric metropolis that loved him.

During the final years of his life, Sinatra was in ill health and was frequently hospitalised for heart and breathing problems, high blood pressure, pneumonia, and bladder cancer. He made no public appearances following a heart attack in February 1997, but even as poor health slowed him down in his last years, he pugnaciously denied rumours of mental and physical decline.

He died of a heart attack on 14 May 1998 at Cedars-Sinai Medical Center in Los Angeles, with his wife Barbara at his side. He was 82 years old.

Sixty films, millions of recordings, nine Grammies, two Academy Awards, innumerable headlines, rises and falls, tragedies and triumphs, concert tours, TV specials – if a legacy could actually be weighed, Sinatra’s might be the heaviest. Which is probably just the way he would have wanted it.

Video