He remained a member of the Box Tops until August 1969, when he decided to return to school to get a music degree in performance of the upright bass.

During this period he backed artists as diverse as Eddy Arnold, Van Cliburn, Isaac Hayes, the Romeros (Spanish guitarists), Dionne Warwick, and Itzhak Perlman.

In 2017 The Box Tops joined The Happy Together Tour with The Turtles, The Association, The Cowsills, Chuck Negron of Three Dog Night, and Ron Dante of The Archies.

On September 6, 2018, The Box Tops filmed, live before an audience of 1,700, a German TV special in Hamburg Germany.

On November 1, 2018, Cunningham was inducted into the Memphis Music Hall Of Fame, as a founding member of The Box Tops.