Freeman was born in Cleveland, Ohio. In 1935 he began playing in local Cleveland area nightclubs, and also formed a classical music trio for local social functions with his father and his sister Evelyn. Around 1939, he and Evelyn formed a new band, The Evelyn Freeman Swing Band, with fellow teenagers from Cleveland Central High School. Evelyn played piano, while Ernie played saxophone and also began writing arrangements for the band.

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