Chapter 6 - Ethical Culture Fieldston School

“Mr. Sinatra Gets Rejected”
lacked an obvious channel for yearnings that remained inchoate well into his
adolescence. Anyone reading a Sinatra biography looking for a childhood
incident that would foreshadow his future will be largely disappointed; while
there are scattered references to him singing to friends or at family gatherings,
there’s little here to distinguish such an activity from a passion for baseball or a
knack for drawing. Most accounts of his youth emphasize Dolly’s and Martin’s
skepticism about their son’s growing interest in a singing career (they hoped he
would attend nearby Stevens Institute and become an engineer). Though Dolly
eventually bought him a sound system and a car to allow him to pursue his
avocation, one suspects this had less to do with her belief that he could become a
singing star – who, after all, could really make a living doing that? – than it did
her long‐standing strategy of making sure her son had enough money in his
pocket to treat, and thus make, plenty of friends.
The epiphany, virtually everyone agrees, took place in the spring of 1935
when the nineteen year‐old Sinatra took his girlfriend, Nancy Barbato, to see
Bing Crosby, the premier popular singer of his day. Crosby’s appeal had less to
do with the pure beauty of his voice than his ability to exploit the cultural
possibilities of new technology, specifically that of the microphone. By singing in
a smooth, subtly modulated voice – a style that came to be known as “crooning”
– Crosby distinguished himself from more powerful vocalists like Al Jolson and
Sophie Tucker, who attained their pre‐eminence as “belters” who could project
their voices to the far corners of a room. Moreover, Crosby’s image matched his
singing style: that of an elegantly dressed, pipe‐smoking smoking man of leisure.
Ironically, the effect of Crosby’s understated image on young Frank Sinatra was
electrifying. “When I saw that guy on stage,” he reputedly told Nancy,
“something happened to me. It was like I was really up there, not Crosby. I’ve
American History for Cynical Beginners
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