Like many other African-American artists from the era, Simon began singing in his father's Baptist church. He pursued his vocal abilities full-time once the family moved to Richmond (near Oakland, California) in the late 1950s. There Simon joined the Golden West Gospel Singers and became influenced by Sam Cooke and Arthur Prysock. With this, the group decided to turn secular and recorded "Little Island Girl" as the Golden Tones in 1959.

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