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.
Hush Records label owners Gary and Carla Thompson urged Simon to record on his own, and in 1964 Simon scored considerable success on the Vee-Jay label with “My Adorable One”. Simon scored again in 1965 on the Chicago based label with “Let’s Do It Over”, which landed a #13 spot on Billboard‘s R&B chart. However, the Vee-Jay label folded soon after the latter song’s release and Simon found himself traveling across the country singing.