In Dallas, Texas, he appeared with Sophie Tucker; in Las Vegas with Billy Eckstine and Elvis Presley; in Miami, Florida, with Eddy Arnold and the Duke of Paducah; and in Detroit, Michigan, with Pat Flowers, Dorothy Donegan, and Lawrence Welk.
[3][citation needed] After hearing him play in 1952, the "Father of the Blues", W. C. Handy, called Maddox "the white boy with the colored fingers".
In January 1955, he recorded "The Crazy Otto Medley", which was composed of Lou Busch's "Ivory Rag", several German folk songs, and Irving Berlin's "Play a Simple Melody".
Disc jockey Bill Randle of WERE in Cleveland, Ohio, suggested to Randy Wood that Maddox record a version of the song and use "The Crazy Otto Medley" as the title.
[4] Maddox performed The Jack Paar Show in March 1955 and played "The Crazy Otto Medley" on Milton Berle's Texaco Star Theatre on May 31, 1955.
His longest professional engagement was at the Red Slipper Room in Denver, Colorado's Cherry Creek Inn, where he played for seventeen years.
Maddox befriended many more musicians and performers from the ragtime and vaudeville days in his travels, including Glover Compton, Butterbeans and Susie, Candy Candido, Ted Lewis, Gus Van, Glenn Rowell, and Joe Jordan.
[7] A caricature of Maddox was placed in the main dining room of the Hollywood Brown Derby Restaurant next to Paul Whiteman, Rudy Vallee, Hank Williams, and Bill Haley.