Bennett took an early interest in art and music as a youngster, studying those subjects at New York’s High School of Industrial Arts. Due to his father’s passing, though, he eventually left the institution when he was 16. He then found a job to help his family’s financial situation.
To achieve that, Bennett tried his hand as a singing waiter in Italian establishments, maintaining his interest in music. However, the teenager’s life took another turn when the United States Army drafted him during the Second World War. His front-line duties finally came to an end in April 1945.
After the war, Bennett continued to sing in the army, as he performed under the pseudonym of Joe Bari. Subsequently, during 1946, the New Yorker returned home and decided to capitalize on the G.I. Bill. This particular bill was implemented to help veteran servicemen, covering things such as tuition costs.