Witherspoon performed in four of the famed Cavalcade of Jazz concerts held in Los Angeles at Wrigley Field which were produced by Leon Hefflin Sr. His first performance was at the fourth Cavalcade of Jazz on September 12, 1948 and Dizzy Gillespie was the featured artist along with Frankie Lane, Little Miss Cornshucks, The Sweetheart of Rhythms, Joe Liggins' Honeydrippers, Joe Turner, The Blenders and The Sensations. The program description states about Witherspoon that "he is one of the most sought-after blues singers in the business. He has a strong, clear voice and diction that you would hear in the classics. Although he has been quite successful singing the blues, Witherspoon can sing ballads with a surprising sweetness." He played at the fifth Cavalcade of Jazz concert on July 10, 1949, along with Lionel Hampton, The Hamptones, Buddy Banks and his Orchestra, Big Jay McNeely and Smiley Turner. Witherspoon came back again for the seventh Cavalcade of Jazz concert on July 8, 1951 and performed alongside Billy Eckstine, Lionel Hampton and his Revue, Percy Mayfield, Joe Liggins' Honeydrippers, and Roy Brown. His last appearance at the eighth Cavalcade of Jazz concert was on June 1, 1952. Also featured that day was Anna Mae Winburn and Her Sweethearts, Jerry Wallace, Toni Harper, Roy Brown and His Mighty Men, Louis Jordan and his Orchestra and Josephine Baker.