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In July 1939, Sinatra recorded “From the Bottom of My Heart,” which didn’t hit the charts, but the following month he recorded “All or Nothing at All,” which became a major hit.The Tommy Dorsey Orchestra was soon upstaging the Harry James Orchestra and Sinatra learned that Tommy Dorsey wanted to sign him.Sinatra’s grandmother scooped him up and held him under cold running tap water at the sink. Frank Sinatra’s father, Anthony Martin Sinatra, was a Hoboken fireman, and his mother, Natalie Della “Dolly” Sinatra (neé Gavarante), was a midwife/abortionist and political activist for women’s rights.While Sinatra’s father was quiet, Dolly overwhelmed her son with love as well as her quick temper.

To his parents’ dismay, Sinatra worked various jobs (including plastering walls for Nancy’s father) during the day and sang at Democratic Party meetings of the Hoboken Sicilian-Cultural League, local nightclubs, and roadhouses at night.

In 1935, 19-year-old Sinatra joined with three other local musicians, known as The Three Flashes, and auditioned to appear on Major Edward Bowes’ very popular radio program, The Amateur Hour.

Accepted, the four musicians, now called The Hoboken Four, appeared on the radio program on September 8, 1935, singing Mills Brothers’ song “Shine.” Their performance was so popular that 40,000 people called in their approval.

At the beginning of 1940, per Sinatra’s request to leave, Harry James graciously tore up Sinatra’s contract.

At the age of 24, Sinatra was singing with the top big band in the nation.

To his parents’ dismay, Sinatra worked various jobs (including plastering walls for Nancy’s father) during the day and sang at Democratic Party meetings of the Hoboken Sicilian-Cultural League, local nightclubs, and roadhouses at night.

In 1935, 19-year-old Sinatra joined with three other local musicians, known as The Three Flashes, and auditioned to appear on Major Edward Bowes’ very popular radio program, The Amateur Hour.

Accepted, the four musicians, now called The Hoboken Four, appeared on the radio program on September 8, 1935, singing Mills Brothers’ song “Shine.” Their performance was so popular that 40,000 people called in their approval.

At the beginning of 1940, per Sinatra’s request to leave, Harry James graciously tore up Sinatra’s contract.

At the age of 24, Sinatra was singing with the top big band in the nation.

Known for his smooth, heartfelt voice during the “crooner-swooner” era, Frank Sinatra started performing in 1935 as the singer of a four-piece band in Hoboken, New Jersey.