Ray joined the Cadillacs after Earl Carroll left to sing with the Coasters. Ray and Roland Martinez brought in former members Bobby Spencer and J.R. Bailery and recorded on Capital Records through 1964.
While with the Cadillacs Ray sang lead vocal on "I Saw You" under the name "Bobby Ray & The Cadillacs", the flip side was a remake of "La Bamba". Ray went on to sing the lead on two other Cadillac songs "Fool" and "The Right Kind of Love". Ray Brewster and The Cadillacs made numerous appearances at the Apollo and traveled throughout the U.S. and Canada.
1963: I saw you/La Bamba - Capitol
1963: Fool/The Right Kind Of Lovin’ - Arctic
1962: White Gardenia/Groovy Groovy Love - Capitol