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Francis Albert Sinatra was born in Hoboken, New Jersey to a family living at 415 Monroe St. in Hoboken. He was the only child of a quiet Sicilian fireman, Anthony Martin Sinatra (1894-1969). Anthony had immigrated to the United States in 1895. His mother, Natalie Dolly Garavanta (1896-1977), was a talented, tempestuous Ligurian, who worked as a midwife, Democratic party ward boss, and part-time abortionist. Known as "Hatpin Dolly," she emigrated in 1897. Although it is part of the Sinatra folklore that Frank had an impoverished childhood, he was actually brought up in a middle-class environment, due to his father's secure job as a fireman and his mother's strong political ties to the Democratic Party in Hoboken. More exactly, the home he was raised in, especially after the age of 5, was comfortably middle-class even as the surrounding neighborhood tipped toward lower middle class.

Following his teen years in New Jersey, Sinatra was interested in serving his country during World War II. But on December 9, 1941, close to his 26th birthday, Sinatra was classified as 4-F at Newark Induction Center, due to a punctured eardrum he suffered from a difficult forceps delivery. This allowed Sinatra to pursue entertainment, rather than being enlisted in the Army Air Corps.

One of Sinatra’s earliest jobs as a singer was at the Hoboken Union Club where, in 1935 he got his first break when his singing group, The Three Flashes, along with Harold Arlen, were approached by talent scout Edward ‘Major’ Bowes. Frank’s mother, Dolly, had been instrumental in getting her son work during these years, and managed to persuade the trio to include Frank, who would appear in non-singing roles - as a waiter and as part of a blackface minstrel group - in promotional films for Major Bowes’ Amateur Hour.

In September 1935 he appeared on the Major Bowes Amateur Hour as part a group called the Hoboken Four. The group won the show’s talent contest with a record 40,000 votes, which led to a national tour with Bowes. Sinatra then took a job as a singing waiter and MC at the Rustic Cabin in Englewood, NJ. (Legend has it that Frank Sinatra was actually not going to get this job but when the first choice Frankie Manion turned down the job, the owner chose Sinatra.) The pay was a mere $15 a week, and Sinatra was left to carry his own public-address system around to local gigs, but the Rustic Cabin gig would allow Sinatra to be heard across New York on the WNEW radio station. In 1939 the wife of bandleader and trumpet player Harry James heard Sinatra on the radio. James, whom Sinatra had been trying to contact via photos and letters, hired Sinatra on a salary of $75 a week and the two recorded together for the first time on July 13, 1939.

Although the Harry James Orchestra never met with a huge amount of success, they were generally well received, and Sinatra, who recorded ten songs with the group for Brunswick and Columbia, gained a great deal of experience, and good notice from the likes of Metronome, during his tenure with the group. At the end of the year he left James to join the Tommy Dorsey Orchestra, where he rose to fame as a ballad singer. His first and biggest hit with the band was 1940s “I’ll Never Smile Again,” which spent several weeks at number one - and was the first “number one” - on Billboard magazine’s then-new chart of America’s top-selling records. His vast appeal to the “bobby soxers,” as teenage girls were called, revealed a whole new audience for popular music, which had appealed mainly to adults up to that time. (The complete span of his career with Dorsey was released in the 1994 box set The Song Is You.)