How Frank Sinatra Became Hoboken’s Favorite Son

Even after Old Blue Eyes traded Jersey for Hollywood, he returned to visit his parents on Hudson Street or to buy chocolate-covered apricots at Lepore’s.

Illustration of Frank Sinatra

Illustration: Raul Arias

Frank Sinatra was 15 when he quit school and began singing at church-basement dances and social clubs in his native Hoboken. 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 of its day. Bowes made Sinatra part of the group and renamed it the Hoboken Four. That episode was short-lived, and Sinatra went back to singing locally.

In spring 1938, when he was 22, Sinatra took a job as a singing waiter at the Rustic Cabin, a roadhouse on a desolate stretch of Route 9W in 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. By that time, Sinatra was living in Hasbrouck Heights with his first wife, Nancy.

As Sinatra’s career took off, he abandoned New Jersey for Hollywood. Still, he often slipped back into Hoboken to visit his parents at the grand home he had purchased for them at 909 Hudson Street or to buy trays of chocolate-covered apricots at Lepore’s on Fourth Street.

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