[2] Born in St. Marys, West Virginia, to Alice (née Evans) and William Masterman, Masters graduated from Robinson High School in southern Illinois.

There he recorded what would become his theme song, "Scatter-Brain," written by Masters and band members Carl Bean and Kahn Keene, with lyrics by Johnny Burke.

[citation needed] Many of these hits incorporated what Masters called "bell tone music," an arrangement gimmick in which chords were staggered, creating, for the time, a trademark sound.

[5] From the mid-1930s through the remainder of his career, Masters largely led hotel house bands in Chicago and New York City that focused on dinner shows and dancing.

Frankie Masters and his Orchestra recorded extensively, producing 124 sides on Vocalion, Okeh, and Columbia between 1939 and 1942, During that same time, they cut several hundred songs for World and Lang-Worth[7] transcription services that provided music to radio stations on a subscription basis and were not released for purchase by the general public.