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Sylvester was born Sylvester James and was raised by his grandmother, blues singer Julia Morgan. After a short-lived gospel career, he performed with the transvestite vocal group The Cockettes.

His backing vocalists included Martha Wash, Izora Rhodes (both of whom went on to form The Weather Girls), and Jeanie Tracy, and his shows were often outrageous and won him a large following in San Francisco’s gay community.

He died of AIDS-related complications in 1988.