Sy Richardson was born in Cincinnati, Ohio, and grew up in Chicago, Illinois. He began singing at the age of twelve and recorded his first record with Lil June and the Januarys at sixteen. He served two years of military service in the United States Navy. Richardson graduated from the University of Boulder with a BS in Advertising Journalism. After a brief stint in several Colorado newspapers, he chose to become an actor and joined the Heritage Square Opera House.
He co-produced and directed the documentary, his direction of "South Of Where We Live" won one of three nominations at the NAACP Image Awards in 1988. Summers In Suffolk was nominated three times for the NAACP Image Awards in 1996. Passing won two out of ten NAACP nominations in 1997.
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