Webster was born in Roanoke, Virginia to Edna Urquhart Webster and Clarence H. Webster. He attended Crystal Spring Elementary, Woodrow Wilson Junior High and Patrick Henry high schools. In 1970 he graduated from Hermitage High School in Richmond. He studied music at Virginia Commonwealth University, majoring in composition. He was active in the Richmond music scene in the 1970s and 1980s performing in several bands, writing music reviews for various free newspapers, working as disc jockey on local radio, and managing a used record store. He also produced the CD Not Necessarily Serious of original folk-rock music by Richmond musician-songwriter Christie Oglesby in 2000. Raised a Baptist, he subsequently became an agnostic. At the time of his death, he was living in Richmond, Virginia, with his long-time companion, Mary Horton; whom he married May 26, 2013.
