Holloway began singing gospel with her mother in the Holloway Community Singers and recorded with Albertina Walker in the Caravans gospel group. Holloway was also a cast member of the Chicago troupe of Don't Bother Me, I Can't Cope. Around this time, she met her future producer, manager, and husband Floyd Smith, and recorded "Rainbow ’71" in 1971, a Curtis Mayfield song that Gene Chandler had recorded in 1963. It was initially released on the Apache label, but shortly thereafter, it got picked up for national distribution by Galaxy Records.