Little is known about Bailey. His voice had a distinctly coarse yet youthful quality. Two of his recordings have survived: "Rowdy Blues" and "Mississippi Bottom Blues". In most digital releases, the tracks are attributed to Willie Brown yet are evidently the same artist credited as Kid Bailey on the original 78-rpm recordings.[9]
It has been remarked that "Although it's almost a cliché to say this about a blues musician from the American South, Kid Bailey was one of the most enigmatic musicians of the era."[10] There has been some speculation that Kid Bailey was a pseudonym of the blues singer Willie Brown.[11]