As John Lennon famously said; “Before Elvis, there was nothing.” Of course, given that he was talking strictly in terms of rock and roll, he was quite right. But when it comes down to effortless cool, style and swagger, nobody preceded Ol’ Blue Eyes. A century since Frank Sinatra’s birth, we’ve all still got him under our skin.


Born December 12th 1915, Francis Albert ‘Frank’ Sinatra was one of the most popular and influential musical artists of the 20th century


Back in the early 1940s, when he really hit the big time with his first solo records, teenage music didn’t exist. Sinatra was The Big Bang Of Pop. He changed everything when he became the first modern superstar, provoking the kind of mass pandemonium that greeted Presley a decade later. While you could easily be forgiven for assuming that Sinatra, like Presley, burst into the spotlight and became an overnight sensation, he had spent years learning his craft singing for bandleaders, Harry James and Tommy Dorsey.

An only child, Francis Albert Sinatra was born to an immigrant Italian family in Hoboken, New Jersey, on 12th December 1915. His Sicilian father, Anthony Martin Sinatra, was a fireman whose mild manner belied his background as a prizefighter, while his domineering, go-getting mother, Dolly, from Genoa, worked as a midwife and Democratic Party activist.

He managed to last only 47 days at A. J. Demarest High School before being expelled for ‘general rowdiness.’ As a teenager, the only thing Frank Sinatra was interested in was music. Ignoring his father’s advice that “singing is for sissies,” he decided to turn professional when he was 18 after he saw Bing Crosby in concert.

He was working as a singing waiter at a New Jersey nightclub called The Rustic Cabin when he was spotted by trumpeter, Harry James, who had recently left Benny Goodman to form his own band. James offered Sinatra a one-year contract worth $75 a week, which was three times what he was making at The Rustic Cabin. There was only one condition. James felt that Sinatra sounded too Italian, so he insisted that he change his name to Frankie Satin, which sounded reassuringly American.

Singer Connie Haines was with them that night, and 50 years later, she could still picture Sinatra’s eyes going cold: “Frank told Harry – ‘You want the singer, take the name.’ And then he walked away.” He may have been desperate for a break, but his position was crystal clear: You don’t mess with Frank Sinatra.

“Is that a name or is that a name?” Sinatra asked journalist, Pete Hamill. “Ladies and gentlemen – the one and only Frankie Satin. If I’d done that, I’d be working cruise ships today. Besides, one fake name in the family was enough,” he added, referring to his father, who boxed under the moniker, Marty O’Brien, because Italians were not welcome in the fight game.

He soon came to the attention of Tommy Dorsey, who needed to find a new singer for his band. Unlike James, Dorsey was a household name, so he was not only able to double his wages, but crucially for Sinatra, he could provide the nationwide exposure he needed before he could become a solo star.

Quincy Jones and Frank Sinatra in the studio together

Quincy Jones and Frank Sinatra in the studio together

On 26th January 1940, Sinatra made his first public appearance with Tommy Dorsey and his Orchestra at the Coronado Theatre in Rockford, Illinois: “You could almost feel the excitement coming up out of the crowds when the kid stood up to sing,” Dorsey recalled. “He was no matinee idol, yet what he did to women was something awful. I used to stand there so amazed I’d almost forget to take my own solos.”

Although Sinatra was only 10 years younger than Dorsey, he saw him as a father figure, copying the way he dressed and studying his trombone playing so that he could develop a more free-flowing singing style. At Dorsey’s insistence, he started running and swimming underwater to increase his lung capacity. He copied the way Dorsey used a small air-hole at the corner of his mouth to sneak breaths between solos, enabling him to hold notes for longer than most singers. Tommy Dorsey’s influence on Sinatra’s sound may not have been as obvious as either Bing Crosby’s or Billie Holiday’s, but it was just as important.

In July 1940, I’ll Never Smile Again reached Number One on the Billboard Charts, where it stayed for 12 weeks. When the US entered World War II, Sinatra’s tender romanticism served as the emotional link between servicemen and the women they had left behind. Over the next two years, Sinatra had 17 Top 10 hits with Dorsey before he asked to be released from his contract to embark on a solo career.


When he strolled into RCA’s Los Angeles studios on the afternoon of 19th January 1942, he looked calm and confident. Sinatra was so excited that he couldn’t wait to play the recordings to Dorsey and the band. Connie Haines vividly remembered the scene as the musicians crowded round the record player and listened to Night And Day for the first time: “Frank was wearing one of those big hats Bing Crosby had made popular. It was slouched down over his head at just the right angle. As the last note ended, we all knew it was a hit.

The musicians cheered. Then I heard him say – ‘Hey, Bing, old man. Move over. Here I come.’”

Sinatra made his last appearance with Dorsey on September 3rd at the Circle Theatre in Indianapolis. Drunk and disconsolate at the prospect of losing his prize asset, Dorsey sat slumped in his chair at the end of the night. He felt betrayed. As they said their goodbyes, Dorsey had only seven short words for him: “I hope you fall on your ass.”

The bobby-soxers didn’t immediately fall for Sinatra’s charms when he made his solo debut supporting Benny Goodman at New York’s Paramount Theatre on December 30th 1942, so his wily publicist, George Evans, paid girls $5 to scream and help whip up excitement in the audience. Sinatra was soon billed as ‘The Voice’, with Evans calling the fans ‘Sinatratics.’ Within weeks of his first appearance, the hype had turned into hysteria as audiences went wild and hundreds of Frank Sinatra fan clubs sprung up all over the United States.

Night And Day sailed straight into the Top 20, the first of a seemingly endless run of hits, but after a couple of years of steadily declining sales, Sinatra looked like a spent force by the beginning of the 1950s. Mitch Miller, head honcho at Columbia, said they “couldn’t give away” Sinatra’s records, so they made him cut a strange mix of soupy love songs and embarrassing novelty tunes in a desperate bid to restore his commercial fortunes.

His film roles quickly dried up, and after years of regularly performing over 100 songs a day, there were very real fears that he might never sing again as his throat began haemorrhaging. Having divorced his first wife, Nancy (the mother of his three children), Sinatra’s stormy six-year marriage to Hollywood actress, Ava Gardner, generated headlines all over the world, with some fans turning against him for leaving his family for a femme fatale.

Sinatra marked the end of a hugely successful 10-year relationship with Columbia on 17th September 1952 when he walked into their 30th Street New York studio for his last recording session for the label. The song was called Why Try To Change Me Now?, and it was about a man who doesn’t fit in, which is exactly how Sinatra felt at the time. It was the perfect parting shot aimed squarely in the direction of Columbia, who had unceremoniously dropped him.

“Fuck him,” Miller screamed at the engineers and record company executives in the control room at the end of the session. “Frank Sinatra’s a has-been.” Many years later, Miller went to shake Sinatra’s hand when they bumped into each other in a Las Vegas hotel lobby. “Fuck you,” Sinatra hissed. “Keep walking.”

His career looked like it was dead in the water, but he was about to stage the greatest comeback in the musical history. In 1953, Sinatra signed a new deal with Capitol Records, who were keen to take his music in a more sophisticated direction.

According to Stephen Bogart, the original members of the Holmby Hills Rat Pack were: Frank Sinatra (pack master), Judy Garland (first vice-president), Lauren Bacall (den mother), Sid Luft (cage master), Bogart (rat in charge of public relations), Swifty Lazar (recording secretary and treasurer), Nathaniel Benchley (historian), David Niven, Katharine Hepburn, Spencer Tracy, George Cukor, Cary Grant, Rex Harrison, and Jimmy Van Heusen. In his autobiography The Moon's a Balloon, David Niven confirms that the Rat Pack originally included him but neither Sammy Davis Jr. nor Dean Martin.

According to Stephen Bogart, the original members of the Holmby Hills Rat Pack were: Frank Sinatra
(pack master), Judy Garland (first vice-president), Lauren Bacall (den mother), Sid Luft (cage master),
Bogart (rat in charge of public relations), Swifty Lazar (recording secretary and treasurer), Nathaniel
Benchley (historian), David Niven, Katharine Hepburn, Spencer Tracy, George Cukor, Cary Grant, Rex
Harrison, and Jimmy Van Heusen. In his autobiography The Moon’s a Balloon, David Niven confirms that
the Rat Pack originally included him but neither Sammy Davis Jr. nor Dean Martin.

After spending two weeks on location in Hawaii filming From Here To Eternity, Sinatra stepped into KHJ Studios in Hollywood for his first session with Nelson Riddle, who was Nat ‘King’ Cole’s Musical Director. After listening to the finished mix of I’ve Got The World On A String, Sinatra was fizzing with excitement: “I’m back, baby. I’m back.”

Although Sinatra cut some of his best-known material with Billy May, Gordon Jenkins and Quincy Jones, it is the iconic albums recorded with Riddle such as In The Wee Small Hours, Songs For Swingin’ Lovers and A Swingin’ Affair that are widely regarded as his finest body of work. At the peak of his powers in the mid 1950s and early 1960s, nobody did it better than Sinatra. It’s no exaggeration to say that he laid down the blueprint for the Great American Songbook. His interpretations were immediately accepted as definitive. However many different versions you hear of those songs, it’s Sinatra who owns them.


By the time he released his seminal Only The Lonely album in 1958, Sinatra sounds like an utterly broken man, his voice heartbreakingly forlorn, shot through with pathos and pain. If you listen to One For My Baby (And One More For The Road), Riddle’s beautifully understated arrangement sounds so sad that from the moment Bill Miller eases into his mellifluous piano introduction, you can tell what state Sinatra is in before he has even opened his mouth to sing. He was still reeling from his recent split with Ava Gardner, and you can hear his pain in every note. “It was Ava who taught him how to sing a torch song,” Riddle once said. “She was the greatest love of his life, and he lost her.”

On the set of The Children’s Hour, Dean Martin, Audrey Hepburn, William Wyler, Frank Sinatra and Shirley MacLaine

On the set of The Children’s Hour, Dean Martin, Audrey Hepburn, William Wyler, Frank Sinatra and
Shirley MacLaine

Whereas Bing Crosby and Louis Armstrong sound like they were performing when they sang, Sinatra sounds like he is confiding in the listener. He’ll open up his heart to you and let you know what he’s really feeling. Sure – he’s tough and he’s cool, but he’s also sensitive. To sing like Sinatra, you’ve got to have had your heart broken.

So what exactly is it about Frank Sinatra’s voice that can make women go weak at the knees and reduce tough guys to tears? With his impeccable jazzman’s timing, understated, conversational delivery and modest virtuosity, Sinatra was technically head and shoulders above his peers, but it was his uncanny ability to dig deep into the emotional heart of a song that really set him apart. It’s the way his voice makes us feel that keeps us returning to Sinatra time after time, year after year.


In 1961 he signed to Reprise, yet of the numerous LPs he recorded for the label, only a handful are on the same level as his Capitol classics. His voice gradually became a shadow of what it once had been. By the time Theme From New York, New York limped into the charts in 1980, Sinatra’s time as a serious recording artist was up.

If nothing survived of Sinatra but what has been said about him, posterity would have a very misleading impression of both his life and his music. If you had never actually listened to the songs but had heard all the juicy details of his episodic and glamorous private life, the one thing you would probably be left with is a sense of bigness; big voice, big life, big star. The Big Boss. He wasn’t called The Chairman for nothing.

For all of the hype and the hubris that surrounded him throughout his career, Sinatra was an extremely private, often introverted man whose life was blighted by long periods of depression. He is known to have made at least three attempts to take his own life. Both behind the microphone and behind closed doors, Sinatra projected a paradoxical cocktail of cocksure confidence, brooding melancholy and deep vulnerability.

His private life may seem to have been played out in the full glare of the spotlight, but he invariably declined interview requests and rarely let anyone outside his tight inner circle get too far past his public persona. The only place Sinatra really revealed himself was in his songs. He was an astonishingly sensitive and intuitive interpreter who always sang from the heart, giving the words just the right emphasis and weight. Sinatra may have been singing lyrics written by others, but he somehow made each song seem first-person autobiographical.

Whether he was performing a finger-popping swing number or a sad ballad, whether it was Cole Porter or Irving Berlin, no other singer made you believe in a song quite like Sinatra. He made each and every line his own and had a unique ability to get inside the song in a conversational way. Sinatra sang to you, not at you.

“Being an 18-karat manic-depressive, and having lived a life of violent emotional contradictions, I have an over-acute capacity for sadness as well as elation,” Sinatra once said. “Whatever else has been said about me personally is unimportant. When I sing, I believe. I’m honest.”