Ruby's thoughts of a career as a singer were initially thwarted in 1926 at Bessie's insistence, but they continued traveling together on tour.
In Atlanta, Georgia, Ruby spent a night in jail after being caught bringing moonshine for her aunt to consume.
In 1927, Ruby was part of the female entourage led by Bessie to the "buffet flats" in Detroit, Michigan.
"[4] Later Jack Gee, who was married to Bessie at the time, once implored Ruby to take the musical stage after her aunt had walked out in Indianapolis, Indiana.
In December 1941, backed by an ensemble led by Sammy Price, she recorded two more tracks, "Why Don't You Love Me Anymore?"