Frank Sinatra Biography: Most Influential Artists of the 20th Century?

He was one of the most influential and talented entertainers the world has ever seen. But he was also one of the most complex – generous and loyal friend, champion of the underdog, devoted family man, womanizer and volatile, loud-mouthed tough guy. He lived a life on the edge – full of excitement, danger and passion. Sow, just how did the skinny Italian kid from New Jersey became an international superstar and the world’s first true multi-media artist? In this week’s Biographics we go behind the veneer to get up close with the Chairman of the Board.

Early Years


Francis Albert Sinatra was born on December 12th, 1915 in Hoboken, New Jersey. He was the only child of Italian immigrants, Martin and Dolly Sinatra. As such he was pampered by his parents, who lavished the best of what they could afford on their son. Still, little Frankie grew up lonely and alone.

Young Frank Sinatra

Young Frank Sinatra

Martin Sinatra was a down to earth, easy going and hard- working City Fireman. His mother was just the opposite, driven, involved in political issues and proving herself the driving force of the family. She belonged to every organization in Hoboken and had a reputation as an extremely dominating character.

While both of his parents worked, young Frank learned to look after himself. If he wasn’t home alone, he’d be wandering the neighbourhood, where he quickly discovered how to become street smart. He grew up in a world of prohibition, bootleggers and Speakeasies.

School was never a priority for the teenage Frank. He would often skip class to hang out in pool halls, boxing gyms and on street corners. He soon developed a reputation as a stubborn, ornery kid who never backed down. Often the subject of racial taunts, he would never let an insult pass. A friend recalled that once he and Frank were walking down the street when someone said, ‘Hey you little wop,’ to Frank. His friend told him to keep on walking but an enraged Frank blurted out, “I’m gonna’ walk all over his face!”

The only problem was that Frank didn’t really know how to fight. He got beaten to a pulp. When his friend asked him if it was worth it he replied . . . Hell, yeah . . . He’ll never call me a wop again.

However, two days later, the same thing happened again – same guy, same result.

Sinatra (far right) with the Hoboken Four on Major Bowes' Amateur Hour in 1935

Sinatra (far right) with the Hoboken Four on Major Bowes’ Amateur Hour in 1935

By the age of sixteen, Frank had ditched school altogether. He worked at a series of odd jobs, including as a dockworker and newspaper boy. But he often got bored and would quite a solid job after just a few weeks. When he walked out on his job working in the refrigeration units of cargo ships, his father had had enough. He referred to his son as a ‘quitter’ and told him . . .

If you want to be a bum, go somewhere else and be a bum.

Frank didn’t have to be told twice. He packed up his few belongings in a suitcase and took the train to New York City. By now he had set his sights on making it as a singer. But no doors opened for the skinny Italian kid. He couldn’t find any employment at all, let along a signing gig. With nowhere to stay and no money for food, he headed home.

“The best revenge is massive success.” Frank Sinatra

Outwardly Dolly mocked her son’s singing ambitions, referring to him as Mr Big-Shot Singer before smacking him on the head. But behind the scenes, she began visiting clubs and asking managers to give her boy a chance. This resulted in a short-term gig in a Hoboken club. But the job didn’t last – Frank got into a fight with the proprietor and was shown the door.

When he was seventeen, Dolly and Marty lent Frank sixty-five dollars so he could buy a portable public address system and sheet music arrangements. This put him a step ahead of other aspiring club performers. Frank then began collecting orchestrations. He later explained his strategy . . .

Bands needed them. I had them. If the local orchestra wanted to use my arrangements, and they always did because I had a large and up-to-the-minute collection, they had to take singer Sinatra too.

In this way, Frank managed to establish a foothold in the local club scene. His hero was Bing Crosby, and he tried to copy the Crosby sound. But when he noticed virtually every other singer out there was doing the same thing, he made the decision to establish his own unique sound.

Frank, Nancy & Success

In the summer of 1934, the eighteen-year-old Frank met seventeen-year-old Nancy Carol Barbato, who came from a poor family in Jersey City, New Jersey. Nancy was sitting on her front porch doing her nails when Frank walked up to her with a ukulele in his hand. His opening line was . . .


Yo, what about me. I could use a manicure too!

Candid photographs of Frank Sinatra and first wife Nancy c. Frank and Nancy (née Barbato) met in the summer of 1934

Candid photographs of Frank Sinatra and first wife Nancy c. Frank and Nancy (née Barbato) met in the summer of 1934

The spark was lit and the romance blossomed over the next four years. They lived one town apart and Frank would frequently take the bus to visit and date Nancy.

During these years, Frank was building his singing experience. Most gigs would pay around two dollars a night. Sometimes he performed at roadhouses for nothing more than a sandwich or cigarettes.

Frank’s first break came on September 8th, 1935 when he auditioned for a spot on the NBC radio show Major Bowes and His Original Amateur Hour. The show was broadcast live from the Capitol Theatre in New York City. Frank teamed up with a group called the Three Flashes and they became the Hoboken Four. They performed the Bing Crosby hit ‘Shine’ and won a spot on the show, which was a 1930’s forerunner to American Idol. Listeners phoned in to vote for their favorite act and the Hoboken Four proved so popular that Major Bowes invited them to return several times.

Sinatra performing at the Rustic Cabin in 1938

Sinatra performing at the Rustic Cabin in 1938

However, the radio show appearances didn’t lead to any lasting success. Frank returned to Hoboken and soon found himself once more begging for any jobs he could find.

In 1939, Frank and Nancy were married. Not long after that Frank was singing in a club called the Rustic Cabin. In the audience was Harry James, a big band leader who was auditioning for a lead singer. James was impressed with Frank’s way of talking a lyric. He invited Sinatra to audition the next day. Although there were a lot of others who showed up for the job, when Frank opened his mouth the matter was settled.

He made his debut with the Harry James Band on June 30th, 1939 at the Hippodrome Theater in Baltimore. The rest of that summer and into the fall he toured with the band to enthusiastic audiences.

I feel sorry for people who don’t drink. When they wake up in the morning, that’s as good as they’re going to feel all day.

By 1940 Sinatra’s popularity was growing steadily. Then he switched bands mid-stream, jumping at the chance to sign on with the more famous Tommy Dorsey Orchestra. The deal that Frank struck, though was hardly in his favor. He would give up a third of his earnings for life, plus 10 percent for Tommy’s agent. But all that the young Frank, who had recently become a father, wanted was to sing and be famous. And besides, he would end up with more each week than he was getting with the old band.

With the Tommy Dorsey Band, Frank traveled across the country. He ended up in Hollywood, California. In 1942, the band, with Sinatra out front made a cameo in the MGM move ‘Ship Ahoy.’

With the band behind him Frank had built up his profile. He appeared on the radio, in concert halls, on TV and in the movies. By the end of 1942, he was one of the most well known singers in the country – and he had replaced Bing Crosby as Billboard’s top band vocalist and cut his first record with the band.

Going Solo

By the end of 1942, Frank had made up his mind to go it alone. He was clearly the star attraction of the Tommy Dorsey Band, so, while they may have needed him, he was more than able to hold an audience by himself. When he told Dorsey of his intentions, the band leader was furious. But Frank was determined and finally Dorsey relented. He did insist, however, that the contract for a third of Sinatra’s earnings would remain in place.

Frank decided that he would worry about the contract later. For now he would get out before Dorsey changed his mind.

Sinatra made his solo debut on his 27th birthday, December 12th, 1942. In the audience that night was Bob Weitman, manager of the Paramount Theatre. He was so impressed that he asked Benny Goodman, the King of Swing,  if he minded having Frank on a bill with him at the Paramount. Goodman’s response was  . . .

Who the hell is Frank Sinatra?

He would soon find out.

Sinatra’s appearances at the Paramount made history. It was the start of the type of hysteria, epitomized by screaming and fainting girls, that would later greet Elvis and the Beatles. When Frank hit the stage, the theater erupted with wild scenes that had never been seem before.

In 1944, with his popularity soaring, Frank became a father for a second time. Frank Sinatra, junior joined older sister Nancy at home while their father’s star kept ascending. His record sales topped the billings and he was the most requested voice on the radio.

Losing It

With the end of World War Two, Sinatra’s fame rose to yet another level. He was contracted by Hollywood to star in a series of musicals, each more popular than the last. Yet, in his personal life, things were starting to unravel. He was away from home so much that he hardly saw his wife and children. Then, in 1947, Frank met and fell in love with the beautiful and glamorous actress Ava Gardner. The two began a very public affair, which lost Sinatra quite a lot of popularity among the older demographic. At the same time, the 31-year-old of crooner’s voice was beginning to show signs of strain and he was also being attacked by mainstream media outlets for his support of liberal causes. It was said that his fight against segregation was Communist inspired. Reporters also began claiming that he dodged the draft during the war.

Frank Sinatra and Ava Gardner

Frank Sinatra and Ava Gardner

Leading the print assault on Sinatra was reporter Lee Mortimer. On April 8th, 1947, the two men came face to face at Cirro’s Nightclub in Hollywood. Frank went straight up to the reporter, called him a ‘fruit’ and then proceeded to use him as a punching bag. Frank’s bodyguards quickly broke it up, with Sinatra yelling  . . .

Next time I see you, I’ll kill you, you little degenerate.

Mortimer had Frank arrested and charged with assault and battery. The charge resulted in Sinatra’s gun permit being revoked. Mortimer later sued for $250,000, and the case was eventually settled for $9,000.

Frank Sinatra Quotes About Life, Love and New York!

Unwise Associates

Sinatra never seemed to appreciate that his choice of associates could impact his career. In 1947, not long after the beat up on Mortimer, he went to Havana to meet with mobster boss Lucky Luciano. The mob connection was to stick to him for the rest of his life.

Despite the affair with Ava Gardner, Nancy Sinatra stuck by her husband’s side. She gave birth to a third child, Christina, on Father’s Day, 1948. But the new addition did not bring Frank back into the family fold. His fascination with Ava was greater than ever. Unlike Nancy, Ava could match him drink for drink, cigarette for cigarette and tantrum for tantrum. They were the ideal hard living couple.

That hard living had a price. In 1949, Frank’s voice gave out. That combined with public reaction to his outrageous affair led to plummeting record sales and chart numbers. His radio show was dropped and MGM cancelled his movie contract. It looked like the show was over for the man who had been called The Voice.

Alcohol may be man’s worst enemy, but the bible says love your enemy.

In 1951, Nancy finally divorced from Frank. In short order, Sinatra married Ava Gardner. He had formalized his love life, but it seemed there was nothing he could do to resurrect his failing career. The public had become disenchanted with him, viewing him as a washed up has been.

Coming Back

It was during his period of hardship in the early 1950’s that Sinatra read a book called From Here to Eternity by James Jones. When he learned that a movie version was being planned he became convinced that this could be his road back to the top. He set his sights on securing the role of Private Angelo Maggio. Frank secured an audition and then proceeded to convince the movie’s producers that he WAS Maggio. He won the part – and gave the performance of his life.

Sinatra won the Oscar for Best Supporting Actor. The following month he signed a recording contract with Capitol Records – and his career was back on track. It appeared that losing his fame and then clawing back had changed Sinatra as a singer. He now wore his heart on his sleeve in his performances, sharing his inner struggles with the audience. He became the first, and the best, musical storyteller, and it was this ability that brought him the male audience that he had never had before. In Sinatra they saw the tender tough guy that they wanted to be.

Sinatra’s marriage to Ava Gardner was tumultuous and it ended in divorce in 1957 – but his career was going fro9m strength to strength.

By the late 1950’s, he was well and truly back on top. His Album Come Fly With Me hit Number One and was on the charts for an impressive 71 weeks. At the same time his movie career was hitting new heights. In The Man With Golden Arm he gave an extraordinary performance as a heroin addicted misfit.

The 1960’s saw the emergence of a new brand of popular music – rock and roll. Realizing that he couldn’t ignore it, Sinatra tried to accommodate by bringing out up tempo albums. In the early 60’s Sinatra also became a staunch supporter of John F. Kennedy. However, Frank had maintained his association with key mob figures. Attorney General Robert Kennedy was concerned that Sinatra brought these criminal underworld figures too close to the President. He managed to sever the relationship between JFK and Sinatra.

Sinatra’s last great movie role was 1962’s The Manchurian Candidate, in which he played US Army officer Bennet Marco. After that  he appeared to become bored with movies and developed a reputation as a troublemaker on the set. His attention had switched to Las Vegas, the new gambling capital of the nation. There he and his buddies became known as the Rat Pack. Along with Dean Martin, Sammy Davis Junior, Peter Lawford and Joey Bishop, Sinatra performed a mixture of stand-up comedy and lounge music at the best casinos in town.

Rat Pack

Rat Pack

Then, in December of 1963, Sinatra’s fun loving existence was jarringly interrupted when his 19-year-old son, Frank Junior, was kidnapped and held for $240,000 ransom. Sinatra appealed to Robert Kennedy, who called in the FBI. The ransom was paid, Frank Junior released, and the kidnappers promptly caught, with most of the ransom being returned.

In 1964, while filming Von Ryan’s Express, Sinatra noticed a young actress named Mia Farrow hanging around the set. The star of a popular night time soap opera, Farrow, at just 19, soon became Sinatra’s constant companion. The 30 year age gap provided plenty for the gossip columnists to get their teeth into.

I like intelligent women. When you go out, it shouldn’t be a staring contest.

In 1965, the 50-year-old singer won an Emmy for the best Television Special of the Year. The following year he recorded one of his most popular albums of all time, Strangers in the Night. That same year, 1966, Sinatra and Mia were married. However, Mia’s mellow hippie style was out of step with Frank’s hard living ways and the union only lasted sixteen months.

Following the divorce and finding himself in danger of being yesterday’s news, Sinatra began looking for a new musical direction that would allow him to compete with the hard-edged rock and roll that was popular at the time. He found what he was looking for in the form of the song ‘My Way’, written by Paul Anka. The song, which Frank recorded in 1969, has become his anthem.

In 1970, to the shock of his legion of fans, Sinatra announced his retirement. He said that he was tired of show business and wanted nothing more than to relax, read and think. But just as he prepared to take life easy, life threw another curve ball his way. He was summoned to a congressional hearing keen to investigate his connections with the mafia. Lack of evidence forced the Congressional committee to drop its investigation and the heat went off Sinatra.

Retirement never sat easily with Frank and, by 1973, he was once again on the comeback trail. This time his focus would be on concert performances. He leapt back into the public consciousness with a television special called ‘Ol’ Blue Eyes Is Back.’ From there he went on fill all of the concert halls and big arenas across the country. He sang directly to his audience dressed in a fitted tuxedo – just as he had always done.

In 1976, the 60-year old Sinatra married for the fourth time. His bride was 45-year-old Barbara Marx. She travelled with him as he played to ever growing crowds.

You gotta love livin’, baby, ’cause dyin’ is a pain in the ass.

By the 1980’s the Chairman of the Board was a bona fide icon. He campaigned for Ronald Reagan, and helped produce his second inaugural. Then, in 1988, the 73-year-old paired with some of his former Rat Pack performers. The audiences loved it.

 More details Sinatra is awarded the Presidential Medal of Freedom by President Ronald Reagan.

More details Sinatra is awarded the Presidential Medal of Freedom by President Ronald Reagan.

In 1993, Frank made use of a technological innovation to produce an album entitled ‘Frank Sinatra Duets.’ He sang along with 13 top recording artists, though they were at different place and times. The record became a number one platinum bestseller, and outsold any of his previous recordings. After more than a century he was back on top.

Sinatra lived out the last five years of his life in relative quiet. He was plagued by ill health, often going into hospital with cardiac complaints. Then dementia set in. He passed away on May 14, 1998 at Cedar Sinai hospital in Los Angeles with the official cause of death being heart attack.

On May 15th, the Empire State building was turned blue in New York and the casinos in Las Vegas came to a halt in tribute to the man who, very uniquely, did it his way.

Frank Sinatra Video Biography

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