In the 1960s, Cummings was a member of the Chocolate Papers, along with Ray Sawyer, Bill Francis, Bobby Dominguez, Popeye Phillips, and Jimmy "Wolf Cub" Allen.
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.
While playing the Bandbox club in Union City, the owner asked George what the name of his band was, and on the spur of the moment, he wrote down "Dr. Hook & the Medicine Show, Straight from the South, serving up Soul Music".
[4] In 2003, Cummings worked with Ken Hatley on the soundtrack for Florida City, a film drama about advance knowledge of the Pearl Harbor attack.
In the spring of 2004, the Flares were reborn in Lebanon, Tennessee when Cummings joined original members Jim Pasquale (guitar) and Norman "Knobby" Lowell (drums), along with Nashville singer-songwriters Scotty Cothran, Harold Hutchcraft, Jack Bond, and Forest Borders, to cut the comeback album, It Is What It Is.