Frank Sinatra

Before Elvis Presley, the Beatles, and all the teen idols who followed in their footsteps, there was Frank Sinatra: a skinny kid from New Jersey who became one of the most sought-after performers in the entertainment industry. Hailed by many as the greatest American singer of 20th-century popular music, Sinatra combined a smooth baritone voice with peerless lyric phrasing to elevate standards of the Great American Songbook into aural works of art. He went on to become an Academy Award-winning actor and a Las Vegas icon with his effortlessly cool “Rat Pack” crew.

Throughout Sinatra’s long career, there were many bumps in the road, from romantic heartaches to persistent rumors of Mafia connections. But the ups and downs of his very public personal life hardly mattered to his fans—or perhaps his troubles were essential to his image. Decades after his death he remained, in the eyes of many, the “Chairman of the Board.”

The boy from Hoboken

Born on December 12, 1915, in Hoboken, New Jersey, Sinatra was the son of Italian immigrants and an only child. His father, Martin, was a Sicilian immigrant, a tavern owner, and a part-time prizefighter. His Genoese-born mother, Natalie (née Garavente)—known to all as “Dolly”—was a formidable influence both in local politics and in her son’s life and career. Upon hearing the recordings of singer Bing Crosby, who had become a star with his mellow “crooning” style, Sinatra was inspired as a teenager to choose popular singing as a vocation. He joined a local singing group, which, as the Hoboken Four, won a talent competition in 1935 on the popular radio program Major Bowes’ Amateur Hour. The group toured the country that year, but Sinatra was the only member with serious musical ambitions, and they soon disbanded.

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For the next few years, Sinatra sang with local dance bands and for remote radio broadcasts. In 1939, while singing and waiting tables at the Rustic Cabin in Englewood Cliffs, New Jersey, he was discovered and hired by jazz trumpeter Harry James, who had recently quit the Benny Goodman Orchestra to start his own band.

The band singer

Sinatra’s six-month tenure with the James band resulted in 10 commercial recordings featuring the young singer. On songs such as “From the Bottom of My Heart,” “My Buddy,” and “Ciribiribin,” Sinatra’s warm baritone and sensitivity to lyrics are well showcased. The best-known of the James-Sinatra sides is “All or Nothing at All”—a flop in 1939 but a million-seller when rereleased in 1943, after both men had become stars. Sinatra’s reputation among industry musicians grew swiftly, and James graciously freed Sinatra from his contract when the singer received a more lucrative offer from bandleader Tommy Dorsey in December 1939. The 83 commercial recordings (as well as several surviving air checks) that Sinatra went on to make with the Dorsey band from 1940 to 1942 represent his first major body of work.

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Sinatra was enormously influenced by Dorsey’s trombone playing and strove to improve his breath control in order to emulate Dorsey’s seamless, unbroken melodic passages. It was also during this period that Sinatra proved his mastery of both ballads and up-tempo numbers, and Dorsey arrangers Axel Stordahl, Paul Weston, and Sy Oliver soon tailored their arrangements to highlight Sinatra’s skills. Often teamed with singer Connie Haines, or with Dorsey’s vocal group, the Pied Pipers (featuring future recording star Jo Stafford), Sinatra was featured on memorable sides such as “I’ll Never Smile Again,” “I’ll Be Seeing You,” “Without a Song,” and “Oh! Look at Me Now.”

By 1942 Sinatra’s fame had eclipsed that of Dorsey, and the singer yearned for a solo career—a risky venture in the days when few big-band singers found success on their own. Dorsey enjoyed having such a popular performer in his band and became irate when Sinatra expressed his desire to leave, even though Sinatra offered to stay with the band for another year. After months of bitter negotiations, Sinatra left the Dorsey organization in late 1942; within weeks, he was a cultural phenomenon. Near-hysteria was generated by Sinatra’s appearances at New York’s Paramount theater in January 1943, and such throngs of screaming, young female fans—known as “bobby-soxers”—had not been seen since the days of silent film star Rudolph Valentino. The singer was soon dubbed “Frankieboy,” “The Sultan of Swoon,” and, most popularly, “The Voice.”

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In many respects Sinatra was the prototype for the teen idols that would soon become ubiquitous in 20th-century pop culture. Yet he humbly saw his early fame as a mere diversion. He once said of this time, “It was the war years, and there was a great loneliness. And I was the boy in every corner drugstore, the boy who’d gone off drafted to the war. That’s all.”

The Columbia years

A strike by the American Federation of Musicians against the major record companies curtailed Sinatra’s recording output during most of 1943–44. His solo recording career for Columbia Records began in earnest in November 1944, when he compensated for lost time by recording dozens of sides within a three-month period. Songs such as “If You Are But a Dream,” “There’s No You,” “I Fall in Love Too Easily,” “Nancy,” and his theme song at that time, “Put Your Dreams Away,” are some of the first recordings in what would come to be known to fans as the “Columbia era” (1943–52). His chief arranger during these years was Axel Stordahl, who also left Dorsey in late 1942 to work exclusively with Sinatra. Stordahl’s spare string arrangements on beautiful recordings such as “You Go to My Head” (1945), “These Foolish Things” (1945), and “That Old Feeling” (1947) defined the sound of Sinatra’s Columbia years.

Sinatra’s success continued unabated until about 1948. In later years, he speculated that his sudden drop in popularity was because of his reluctance to change styles and evolve musically. He also garnered a great deal of negative press throughout 1947–48. It was about this time that the public first read reports of his friendships with organized-crime figures, and newspaper accounts were published of Sinatra cavorting in Cuba with the likes of Lucky Luciano and Joe Fischetti, both prominent mobsters. There was also the widely reported incident, and resulting lawsuit, in which Sinatra punched gossip columnist Lee Mortimer after the journalist allegedly called the singer an ethnic slur. Sinatra received some vindication for the action in later years when it was revealed that Mortimer had collaborated with the FBI to discredit him.

Whatever the cause, Sinatra began a five-year period of professional decline and personal depression. Years of singing as many as 100 songs per day had taken its toll, and he lost his voice completely for several months in 1950 because of vocal-cord hemorrhaging. His divorce from first wife, Nancy (née Barbato), in 1951 and his subsequent stormy marriage to actress Ava Gardner further harmed his reputation. In addition, then-new Columbia Records president Mitch Miller cajoled Sinatra to record several banal novelty tunes that compromised his artistic credibility. In 1952 his Columbia recording contract came due and was not renewed, he was dropped by his talent agency, his network television show was canceled, and Sinatra was considered a has-been. Ironically, and despite Miller’s demands, several of Sinatra’s recordings from this period are now considered among his best, with shining examples such as “Mad About You,” “Nevertheless,” “Birth of the Blues,” and, especially, his 1951 recording of “I’m a Fool to Want You.”