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.   Read More: thebiographychannel.co.uk