In the 1960s, Cummings was a member of the Chocolate Papers, along with Ray Sawyer, Bill Francis, Bobby Dimingus, Popeye Phillips and Jimmy "Wolf Cub" Allen.
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The Chocolate Papers toured clubs in Mississippi, Alabama and South Carolina, before settling in Biloxi as the house band at the popular 800-seat Gus Stevens Restaurant, the first Gulf Coast supper club to offer upscale entertainment with such headliners as Elvis Presley, Andy Griffith, Mel Tormé, Jayne Mansfield and Mamie Van Doren.
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