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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 tiny Apache label, but shortly thereafter, it got picked up for national distribution by Galaxy Records.

In the early 1970s, Holloway signed a recording contract with the Atlanta-based soul music label Aware, part of the General Recording Corporation (GRC), owned by Michael Thevis. Holloway recorded two albums for the label, both of them produced by Floyd Smith—Loleatta (1973) and Cry to Me (1975). Holloway later married Smith. Her first single from the second album, the ballad "Cry to Me" rose to #10 Billboard R&B and #68 on the Hot 100, but before the label could really establish Holloway, it went out of business.