Ruby was all of 14 years of age when her voice was first noticed by the pianist of the Shady Grove Baptist Church in her hometown of Plumerville, Arkansas and she was selected to be lead singer of the gospel choir. That gave her the opportunity early in life to sing and tour numerous towns around Arkansas. At home, her parents played gospel, blues, and R&B music. They noticed her love for music and bought Ruby her first record player as a Christmas present. Ruby would spend hours studying the songs and learning how to put her own feelings and style into the lyrics. She moved to Washington, DC in the early 1970's and made her professional singing debut at the L'Enfant Plaza Hotel as part of the Al Martinez jazz combo.

Later she honed her skills in a rhythm and blues band called the Exclusives and performed in military officers clubs and major hotel ballrooms around the Washington, DC metropolitan area. 1975 was a turning point for Ruby when She met her friend and mentor Linda Hopkins during the time she was performing "Me and Bessie" at Ford's Theatre in Washington, DC. It was this relationship that inspired Ruby to start her own jazz and blues band, the Ruby and James Quartet.