Frank Sinatra


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Francis Albert Sinatra was the only child of two Italian immigrants. His father was Anthony Sinatra, a New York fireman of Sicilian origin, and his mother was Natalie Garavanta, who was usually called by her middle name, Dolly.

Sinatra’s mother was often called “Hatpin Dolly”, and was well known for her fiery volatile Ligurian personality. Sinatra’s parents had both emigrated from mainland Italy to America in the 1890s, and the family enjoyed a reasonable standard of living, thanks to Anthony’s secure job in the Fire Department, as well as his mother’s political connections with the Democratic Party in Hoboken. Dolly was a local political ward boss, as well as working as a midwife.

Young Sinatra enjoyed a stable, comfortable upbringing and he was keen to enlist for the armed services during World War II, following the Japanese attack on Pearl Harbour. But when he attempted to sign up at the age of 26, he went for a medical check-up and was pronounced unfit for active service, owing to a punctured eardrum that he’d sustained at birth. It’s likely that Sinatra’s failure to enlist caused him to place even greater emphasis on his emerging career as an entertainer.

Sinatra had already embarked on his performing career, thanks to the help of his mother, who had found work for him singing in a group called The Three Flashes. One of his first engagements was at the Hoboken Union Club, and it was here, in 1935, that he got his first “big break”. The Three Flashes were approached by talent scout Edward “Major” Bowes, who then offered Sinatra work performing in a number of promotional films for his series, 'Amateur Hour'.

In September 1935, Sinatra took part in a talent contest organized by Edward Bowes, and won first prize: this led to a national tour. When the tour was over, Sinatra took a job as a singing waiter and MC at a venue called the Rustic Cabin. The pay was only $15 per week, but the Rustic Cabin gigs were also broadcast across New York on the WNEW radio station. Sinatra’s voice was now being heard by a far wider audience than before. In 1939, the wife of bandleader and trumpet player Harry James heard Sinatra singing on the radio, and persuaded her husband to give Sinatra a job. Harry hired Sinatra for the princely sum of $75 per week, and the two artists made their first joint recording in July 1939, as war was looming in Europe.

Working with Harry James was great experience for Sinatra, despite the fact that the band never made the big time. Sinatra and Harry recorded ten songs together. Shortly afterwards, Sinatra was offered a job with the Tommy Dorsey Orchestra, where he began to make his mark as a ballad singer. His first (and biggest) hit with his new band was the 1940s smash, 'I’ll Never Smile Again', which was also, by coincidence, the first ever Number One on Billboard magazine’s brand-new chart of America’s best-selling records. Sinatra’s gentle charisma and easy-listening crooning style made him an instant hit with the nation’s millions of teenage girls, known at the time as “bobby-soxers”, and his records began to sell in vast quantities.

Frank Sinatra cut a staggering total of 29 singles with Tommy Dorsey during 1941, which led to his being named Male Vocalist of the Year by Billboard Magazine. Sinatra stayed with the Dorsey Band until August 1942, when he left to pursue stardom as a solo recording artist.


In 1943, Sinatra signed a contract with Columbia Records, and was instantly successful. His career was no doubt given a further boost owing to the fact that there was a musicians’ strike in progress at the time his first records came out. He scored several hits during the strike, including the sensational 'Saturday Night is the Loneliest Night of The Week'. Sinatra also starred on many radio programs during the 1940s, and soon began to be thought of as the nation’s second most popular male singer, running a close second to Bing Crosby, whose audiences at the New York Paramount he had actually succeeded in topping.

“Sinatra-Mania” was now in full swing - Sinatra scored a phenomenal 23 top ten singles between 1940 and early 1943 alone: to show their appreciation of his talent, his American fans affectionately nicknamed him “The Voice”.

In 1943, Sinatra made his debut at New York’s famed Madison Square Garden. He then caused a sensation whilst playing to an audience of over 10,000 people at the Hollywood Bowl. Sinatra’s concert was so profitable that the Bowl’s financial difficulties were resolved in one stroke. Wowed by Sinatra’s relaxed charm, Hollywood producers soon came knocking on his door. He signed a seven-year contract with RKO, and appeared in a string of light musical films, including 'Step Lively' and 'Higher and Higher'.

Again, teenage fans made up his biggest audiences - a fact that did not go un-noticed by Louis B. Mayer - who bought his contract with RKO and signed him to MGM under a $1.5 million contract. Sinatra was now one of America’s top movie stars, and when he returned to New York’s Paramount for a concert, a crowd of over 35,000 fans caused a near riot - later known as the Columbus Day Riot. Sinatra’s fame during the 1940s was truly phenomenal: at one point, it was estimated that he had over 40 million fans!

In 1945, Sinatra starred in his first film alongside Gene Kelly, 'Anchors Aweigh'. This film was an instant success, sparking a string of movies in which he co-starred with Kelly. His singing career was also booming, and by 1946, he was performing as many as 45 shows a month at some periods.

The 1940s turned out to be Sinatra’s golden decade, and by the end of 1948, he himself suspected that his career was slipping from the pinnacle of success. This was reflected by the fact that he only reached No. 5 on Down Beat’s annual poll of most popular singers. As sales of his records slipped, Sinatra tried new ways of singing, such as gospel songs and novelty tracks. But his fortunes revived in 1949 as he co-starred with Gene Kelly again in 'Take Me Out To The Ball Game' - which was followed up by a further success in 'On The Town'.

Encouraged by his box office successes, Sinatra returned to the concert stage in January 1950, selling a staggering $18,000-worth of tickets for just two nights of performing - but an overly packed schedule of singing resulted in Sinatra’s haemorrhaging his vocal cords during a gig at the Copacabana night-club. He was forced to cut back on his commitments for a while, but bounced back to give a sell-out concert at the London Palladium in July 1950.


In 1951, he gave his debut performance at the Desert Inn in Las Vegas - a city that was to become the main arena for his singing over the ensuing decade. Elsewhere, his popularity was waning, as his appeal to teenage audiences fell. But Sinatra did have a few hits over this period, such as 'Goodnight Irene', 'Castle Rock', 'Bim Bam Baby', etc. and he continued to work extensively in radio, cabaret and television.

The slump that marked the beginning of the 1950s for Frank Sinatra turned out to be a temporary blip in his career. The massive success of the movie 'From Here To Eternity' in 1953, for which he won an Oscar as Best Supporting Actor, marked the beginning of a major revival in his fortunes. Sinatra was a hugely successful film actor, but his dramatic style was marked by energy and spontaneity, rather than by technique - an approach that earned him the nick-name, “One-Take Charlie”. Critics consider 'The Manchurian Candidate' (1964) to be his best film, but he is probably most famous for the handful of movies he made with his friends, Dean Martin and Sammy Davis Jr., in particular, 'Ocean’s Eleven' (1960) and 'The Detective' (1968) - together, the three actor-performers were known as “The Rat Pack“.

Frank Sinatra was also well known for stormy love life and colourful relationships, which were frequently the object of tabloid attention. Frank married no less than four times; his first marriage was to his childhood sweetheart, Nancy Barbato, with whom he had three children - Nancy, Frank Sinatra Jr., and Christina. The marriage hit the rocks when Sinatra had an affair with actress Ava Gardner. She became wife No. 2, when he married her in 1951. But rumour has it that Sinatra still loved Nancy’s cooking so much, that he would send someone by to pick up her homemade specialities many years after they had parted.

Sinatra’s marriage to Ava Gardner was comparatively short-lived, and they split up in 1953 (but did not divorce until 1957). He then had a romance with Lauren Bacall, which was also short-lived. But whilst he was filming 'Von Ryan’s Express' in 1968, he had a fling with Rafaella Carra, who introduced him to his next wife, actress Mia Farrow, some thirty years his junior. They were divorced two years later. Finally, in 1976, Sinatra married Barbara Blakeley Marx, who became a Catholic in order to marry him. Barbara remained married to Sinatra until the day he died, despite her frequently difficult relationships with his children.

Notwithstanding Sinatra’s unparalleled success as a movie star and singer, his public image was often marred by rumours of his associations with organised crime and the Mafia. The allegations began as early as the 1940s, when Sinatra visited Havana with the Fischetti family, who were known mobsters. Sinatra was also friends with Sam Giancana, a Mafioso who was also linked with the Kennedy family. Giancana always wore a sapphire friendship ring that had been given to him by Sinatra. Despite the fact that J. Edgar Hoover, head of the FBI, suspected Sinatra of Mafia involvement, nothing was ever proved against him, and Sinatra publicly refuted these allegations on many occasions. The character of Johnny Fontane in the famous book and epic film series, 'The Godfather', was also widely believed to have been based on Sinatra, and his Mafia connections, much to Sinatra’s very public annoyance with the author.


Sinatra’s career suffered many ups and downs, but he always succeeded in making a comeback, and performed on the world’s stages right up until the last few years of his life. From his first released single in 1940, as the singer with the Tommy Dorsey Orchestra, to the release in 1980 of 'Theme from New York, New York', Frank Sinatra had an amazing total of 209 hits on Billboards pop singles charts. Of those, 127 reached the Top Twenty, 70 reached the Top Ten, and no less than 9 singles made it to No. 1! These were: 'I’ll Never Smile Again' (1940), 'There Are Such Things' (1942), 'In The Blue Of The Evening' (1943), 'All Or Nothing At All' (1944), 'Oh, What It Seemed To Be' (1945), 'Five Minutes More' (1946), 'Strangers In The Night' (1966) and 'Something Stupid' (1967).

Of Sinatra’s 55 Top Twenty albums, 41 reached the Top Ten, and 6 made it to number One: 'The Voice of Frank Sinatra' (1946), 'In the Wee Small Hours', 'Come Fly With Me' (1956), 'Frank Sinatra Sings for Only The Lonely' (1958), 'Nice n’Easy' (1960), and 'Strangers In The Night' (1966). His most successful album of all time was the 1997 compilation, 'My Way: The Very Best of Frank Sinatra', released the year before he died. Up until now, this album has charted for 128 weeks, and has earned 5 platinum records.

Sinatra maintained a hugely successful singing career alongside his acting career throughout the 1950s and for several decades beyond. Although he “retired” in the early 1970s, he made a huge comeback in 1973, releasing a special album called 'Ol’ Blue Eyes Is Back' and filming a TV special, to mark the occasion. He also resumed his singing career in Las Vegas, and toured extensively in the Far East, where he was phenomenally popular, especially in Japan. Sinatra toured right up until the 1990s, and was given a Lifetime Achievement Award at the Grammy Awards in 1994.

Failing health kept him out of the public eye after his 80th birthday, and he suffered a heart attack and stroke in 1996, and a further heart attack in 1997. After suffering his 3rd and final heart attack, Frank Sinatra died on 14 May 1998. His funeral in Beverly Hills was a star-studded occasion, with a list of mourners that included Liza Minnelli, Tony Curtis and Gregory Peck. Legend has it that he was buried in a blue suit, with a bottle of Jack Daniels, a pack of Camels cigarettes, a Zippo lighter - and a roll of dimes for good luck.

Get a kick out of this - Frank: The Making of a Legend by James Kaplan

Who was Frank Sinatra? And how did who he was lead to him creating such incomparable music? In FRANK, fans finally have a biography that goes more deeply into who he really was than any previous book about this extraordinary man. 

Revisit some Sinatra classics - My Way: The Best of Frank Sinatra

My Way: the Best of Frank Sinatra collects 46 tracks culled from the estimable American singer's vast back-catalogue for a remarkable two-CD set. These songs are some of Old Blue Eyes' finest works: among the best are 'Come Fly with Me', 'Lady Is a Tramp' and 'I Get a Kick out of You'.

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