Singing guitarist Kid Bailey's historical significance lies in the fact that he collaborated with Charley Patton and a circle of Delta blues musicians who swapped melodies, riffs, and lyrics during the late 1920s and early ‘30s. That web of individuals included Willie Brown (a major influence upon Patton), Tommy Johnson, Ishman Bracey, and Son House. Bailey also sounded like Furry Lewis, Ed Bell, Garfield Akers, and Bukka White. Like Patton, Bailey hailed from Sunflower County in northwest Mississippi, and is said to have been born near Doddsville, south of Drew, which is south of Clarksdale. His first name has never been determined.

Bailey's importance is in no way diminished by the fact that he only cut one 78 rpm phonograph record: Rowdy Blues backed with Mississippi Bottom Blues. His sole session took place on September 25, 1929 at the Peabody Hotel in Memphis, TN, with an unidentified second guitarist. It was issued as Brunswick 7114. Contrary to the connotation of its title, Rowdy Blues is a poignant, wistful love song. Son House later claimed that the recording was by Willie Brown and Charley Patton. He must have been thinking of Brown's grittier M O Blues and Future Blues which are similar to Bailey's Rowdy Blues; as is Patton's Pony Blues.

Bailey and Brown, of course, were distinctly different individuals and still sound that way on their records. Mississippi Bottom Blues seems to have been derived from Freddie Spruell's 1928 recording of Low Down Mississippi Bottom Man. It also has elements in common with Tommy Johnson's Big Fat Mama as well as Patton's Devil Sent the Rain. Bailey continued to perform throughout the Mississippi Delta region until the '50s, without ever managing to make any more records. Like many of his fellow Delta bluesmen, Bailey made music that was, in the words of blues historian Samuel Charters, "…too intensely personal to appeal to any kind of large audience.", Rovi