Sayles was born in Donaldsonville, Louisiana and played violin and viola as a child, then taught himself banjo and guitar.
[1] He went to high school in Pensacola, Florida, then relocated to New Orleans and played with William Ridgely's Tuxedo Orchestra.
Following this he worked with Fate Marable, Armand Piron, and Sidney Desvigne on riverboats up and down the Mississippi River.
Sayles moved to Chicago in 1933, where he led his own group and worked often as an accompanist on blues and jazz recordings with Roosevelt Sykes and others.
Sayles also recorded with Peter Bocage, Kid Thomas Valentine, Earl Hines, and Louis Cottrell, Jr.