Diamond was born in Brooklyn, New York City, and learned the flute and piccolo before winning a harmonica contest held by bandleader Edwin Franko Goldman in Central Park.
They appeared on American Forces Network radio, and in movies including Coney Island, Hi'ya, Sailor (both 1943), Swing Out, Sister and Forever Yours (both 1945).
[2][3] By 1950, Diamond started to establish a solo career, principally as a recording artist, although he also performed in clubs across the US.
He provided the soundtracks to several films, including Miss Sadie Thompson and The Eddie Cantor Story.
"[7] Frank Sinatra championed Diamond, and as a result he signed to Reprise Records when it was established in 1960.