Frank Sinatra: from Hoboken to Eternity


Francis Albert Sinatra was born on December 12, 1915, at 415 Monroe Street in Hoboken, NJ. He was the only child of Italian immigrants Natalina “Dolly” Garaventa and Antonino Martino “Marty” Sinatra. Sinatra weighed 13.5 pounds at the time of his birth and had to be delivered with the aid of forceps, which severely scarred his left cheek, neck, and ear and perforated his eardrum—damage that remained for life.

Dolly, Sinatra’s mother, was energetic, driven, and a force to be reckoned with. She worked as a midwife, and ran an illegal abortion service that catered to Italian Catholic girls. Dolly became influential in Hoboken politics and in local Democratic Party circles. She had a gift for languages and served as a local interpreter.

Sinatra’s illiterate father was a boxer who fought under the Irish name Marty O’Brien. After his prizefighting days were over, he worked for 24 years at the Hoboken Fire Department—a job he undoubtedly landed through Dolly’s connections and influence.


Being an only child, Sinatra was rather lonely growing up. But at the same time, his mother Dolly doted on him and provided money for expensive clothes, causing neighbors to describe him as the “best-dressed kid in the neighborhood.” 


In 1927 the Sinatras moved to 841 Garden Street—a roomy place with three stories and four bedrooms in the more prestigious German/Irish part of town. Frank had his own room on the top floor. They had a baby grand piano in the living room and a gold-and-white telephone.

Sinatra attended David E. Rue Junior High School in 1928, and A. J. Demarest High School (called Hoboken High School today) in 1931, where he arranged bands for school dances. He left without graduating, having attended only 47 days before being expelled for “general rowdiness.”


Dolly and Marty were very upset, but the energetic Dolly found Sinatra work as a delivery boy at the Jersey Observer newspaper. After that Sinatra tried working as a riveter at the shipyard, a job he proved ill-suited for. The teenaged Sinatra soon started singing at bars and clubs in Hoboken, occasionally earning some money.


In 1934 Frank met his future wife Nancy Barbato, a local Italian girl from Jersey City.


Frank Sinatra’s first big break came when he and a local trio which called itself The Three Flashes auditioned for an appearance on Major Bowes and His Original Amateur Hour. The newly-formed quartet named The Hoboken Four won the contest and embarked on a seven-month tour of the central and western United States and Canada.


Sinatra started performing at local Hoboken social clubs such as the Cat’s Meow and Elks. Aggressively pursuing his career as a singer, he also sang for free on local radio stations. To improve his speech, he began taking voice lessons for a dollar each from vocal coach John Quinlan, who was one of the first people to notice his impressive vocal range. He landed his first regular gig at Hoboken’s Union Club for a whopping $40 a week.


Sinatra found employment as a singing waiter at a roadhouse called The Rustic Cabin in Englewood Cliffs, New Jersey, for which he earned $15 a week. The roadhouse was connected to the WNEW radio station in New York City, and he began performing with a group live on air during the Dance Parade show.


In 1939 Frank Sinatra and Nancy Barbato got married in Jersey City, NJ.

The same year Sinatra signed with Harry James, a trumpeter and a band leader, who had just left Benny Goodman to start his own band. Even though the contract had a term of two years, Sinatra only stayed with Harry James for six months since he wanted to pursue better opportunities as a rising star. Frank Sinatra cut his first record with Harry James, “From The Bottom of My Heart.”


Frank Sinatra left the Harry James Orchestra to join Tommy Dorsey’s band, an ensemble which enjoyed extreme popularity and success from the late 1930s through the 1950s. Sinatra stayed with Tommy Dorsey for only two years before embarking on a solo career.

This was the year when Sinatra’s first child, Nancy Sinatra, was born.


After leaving the Tommy Dorsey band, Frank Sinatra embarked on a spectacular solo career. After his “legendary opening” at the Paramount Theatre in New York on December 30, 1942 in front of the thousands hysterical fans his popularity became officially known as “Sinatramania.” The singer was soon dubbed “The Sultan of Swoon,” and, most popularly, “The Voice.”

Sinatra performed for four weeks at the theatre, his act following the Benny Goodman orchestra, after which his contract was renewed for another four weeks.


In the 1940s, Frank Sinatra launched his film career. At first, his films were mostly musicals where his roles remained that of a “boy in a sailor suit.” He starred in Anchors Aweigh in 1944 alongside the musical-comedy superstar Gene Kelly.

At the same time, Sinatra the singer signed with Columbia Records as a solo artist. His chief arranger during these years was Axel Stordahl, who left Dorsey’s big band to work exclusively with Sinatra.

Frank Sinatra Jr. was born.


The House I Live In,” a ten-minute short film starring Frank Sinatra, was made to oppose anti-Semitism in the USA at the end of World War II. The film earned Sinatra an Honorary Academy Award and a special Golden Globe Award.

In 1946 Sinatra attended the Havana Conference in Cuba, where he was invited to sing and entertain the conference attendees. This conference was a historic meeting of United States Mafia and Cosa Nostra leaders arranged by Charles “Lucky” Luciano to discuss important mob policies, rules, and business interests. The delegates at the Havana Conference represented crime families throughout the United States.

The conference appearance badly reflected on Frank Sinatra, contributing to his public image as a mob-affiliate. Sinatra, accused by the press of carrying money to Havana, was put on the FBI watch list.


Sinatra left Hoboken in 1939 when he married Nancy and moved to the neighboring Jersey City. He never came back to his hometown except for a few random occasions. One of them was in 1947 when Frank Sinatra, a huge star by this time, visited his home town of Hoboken to receive the symbolic keys to the city. One the people clearing the crowd is Sinatra’s father Marty.


Following years of overworking his vocal cords on top of habitual smoking and drinking, Sinatra suddenly lost his voice during a live performance.

With no clear indication that his voice could be restored, Sinatra’s career was headed for a painful downturn. During this time many referred to Sinatra as a “has been.”


In 1951 Sinatra met and fell passionately in love with screen siren Ava Gardner. He divorced Nancy Sinatra, with whom he had three children, and married Ava.

The relationship proved to be very turbulent. While Ava Gardner’s career skyrocketed, Sinatra, fearing to permanently lose his voice, experienced the hardest time of his life. Insane jealousy was mutual and well substantiated.

In 1952, the Columbia record company failed to renew his contract.


Without a voice and with his marriage to Ava Gardner crumbling, Sinatra made a miraculous come back. He pleaded with Columbia Pictures president Harry Cohn for the dramatic role of the scrappy, tragic soldier Maggio in the film From Here to Eternity. He felt that he really understood the character, with whom he shared a similar blue-collar Italian heritage, and agreed to play him for very little money. Ava pulled some strings to get him cast for the role, which he admittedly would have done for free.

His performance was universally praised and earned him an 1954 Oscar for Best Supporting Actor. 

About this time, Sinatra’s life and musical style took a dramatic turn. While his love for Ava was causing him a lot of pain and his marriage was ending, his voice came back and his singing acquired depth and emotional complexity. He signed with Capitol Records and, throughout the next nine years, issued a series of recordings that would be widely regarded as his finest body of work. He is credited (though perhaps not accurately so) with inventing the “concept album”—an LP collection of songs built around a single theme or mood. Sinatra’s collaboration with arranger Nelson Riddle was truly legendary. Riddle, a former big-band trombonist who had arranged for artists such as Nat King Cole, scored some of Sinatra’s first Capitol sessions in 1953, initiating a collaboration that would span over two decades and hundreds of recordings. Riddle was, in Sinatra’s words, “the greatest arranger in the world.” 


Sinatra starred in The Man with a Golden Arm, earning a Best Actor nomination. Sinatra delivered a stellar performance in a complex drama proving himself a serious actor.

After his father Marty’s retirement from his job in the Hoboken fire department, the Sinatras moved to the neighboring town of Weehawken.


The turbulent marriage to Ava Gardner ended in divorce. Although Ava filed for a divorce back in 1954, the process was finalized in 1957.


Frank Sinatra won three Grammy Awards for Come Dance With Me!: Album of the Year, Best Male Vocal Performance, and a Special Award: Artists & Repertoire Contribution.


At the behest of Joseph P. Kennedy, Sr., Sinatra acted as a liaison between the Giancana and Kennedy families during John F. Kennedy’s presidential campaign in order to ensure votes for Kennedy. Within a few years, however, the Kennedy administration launched its war on organized crime and disassociated itself from Sinatra, while Giancana, having lost a powerful political connection, did likewise. Sinatra continued to associate with mob figures throughout the years (“If you sing in joints, you’re gonna know the guys that run them,” was Sinatra’s standard defense), but his association with Giancana was perhaps the most publicized.

Frank Sinatra escorting Jackie Kennedy to her box at a gala,

Sinatra was chosen to organize a pre-inauguration gala at the National Guard Armory on the eve of Kennedy’s Inauguration day, January 19, 1961, which is considered to be one of the biggest parties ever held in Washington, D.C. He took turns performing and watching from the Kennedy box. When the president-elect assumed the podium he remarked how indebted he was to Sinatra. But the occasion marked the last time Sinatra would meet with the Kennedys.

Sinatra founded Reprise Records in 1960 and was allowed to record there simultaneously in his Capitol contract, which expired in 1962. Throughout the early 1960s Sinatra recorded at a furious pace, releasing some 14 albums of new material during the years 1961–63. 


The 1960s were the Rat Pack years, probably the funnest period of Sinatra’s life. The Rat Pack was simply a group of friends that hung around the Sands Hotel in Las Vegas, drinking and gambling by day and performing by night. In every show they sang and performed an improvised act of boozy humor for adoring audiences.

Peripheral members of the Rat Pack included actors Peter Lawford, Joey Bishop, and Shirley MacLaine as well as honorary member John F. Kennedy, but the core group always remained Sinatra, Sammy Davis, Jr., and Dean Martin.


Sinatra Jr. was kidnapped on December 8, 1963 at the age of 19 while getting ready to do a show at Harrah’s in Lake Tahoe. He was released two days later after his father paid the $240,000 ransom demanded by the kidnappers. The terrified Sinatra refused help from the mob, going to the FBI instead. The kidnappers were soon captured, prosecuted, convicted, and sentenced to long prison terms, but ended up serving only small portions. The mastermind Keenan was later adjudicated to have been legally insane at the time of the crime and hence not legally responsible for his actions.


Sinatra married actress Mia Farrow on July 19, 1966, when she was 21 and he was 50. They divorced in 1968 after he was angered by her decision not to drop her career. She was filming Rosemary’s Baby at the time. 


Marty Sinatra, Frank Sinatra’s father, died in 1969.

His mother Dolly died in 1977 a plane crash. She was on the way to attend Frank’s performance in Las Vegas when the private jet arranged by Sinatra suffered a fatal accident.


In 1976 Sinatra married  Barbara Marx, the former wife of Zeppo Marx (of the Marx brothers.) The two remained together until Sinatra’s death more than 20 years later.

He announced his retirement in 1971, but by 1973 was recording once again. In his last two decades as a recording artist he chose his projects carefully, releasing only seven albums of new material. His voice grew increasingly gritty and coarse, the product of years of tobacco and alcohol abuse. But learning to turn those vocal shortcomings into interpretive strengths, he produced some of his most poignant records in his later years.

Sinatra virtually retired from films during the latter stage of his career. He concentrated instead on live performance and gave hundreds of international concerts from the late 1970s until his final public performance in 1995. 


The world lost an icon.

Frank Sinatra died of a heart attack at Los Angeles’ Cedars-Sinai Medical Center on May 14, 1998. He was 82 years old and had at last faced his final curtain. His show business career spanned more than 50 years.

Frank with Nancy and the family

1940s – Sinatramania

1950s – Frank Sinatra and Ava Gardner

1960s – The Rat Pack Years

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