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How Frank Sinatra Became Hoboken’s Favorite Son

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How Frank Sinatra Became Hoboken’s Favorite Son


Illustration of Frank Sinatra
Illustration: Raul Arias

Frank Sinatra quit school at 15 and began singing in Hoboken social clubs and church basement dances. He hooked up with a trio called the Three Flashes, and together they passed an audition for Major Edward Bowes’ Amateur Hour radio program—the American Idol The best of its time. Bowes brought Sinatra into the group, renaming it the Hoboken Four. Sinatra soon returned to his local singing.

Sinatra, then 22, took a singing-waiter job at the Rustic Cabin in spring 1938. The roadhouse was located on a lonely stretch of Route 9W, near Englewood Cliffs. That’s where the popular bandleader Harry James discovered Sinatra and signed him to sing for $75 a week. Next, Sinatra joined Tommy Dorsey’s band and sang his way to national stardom.

Splitting from Dorsey, Sinatra made his solo debut at Newark’s Mosque Theater. That led to his historic sold-out performance on December 30, 1942, at New York’s Paramount Theater. Sinatra lived in Hasbrouck Heights, New York, with his first spouse, Nancy, at that time.

As Sinatra’s career took off, he abandoned New Jersey for Hollywood….



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