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Cynthia Calhoun was born and raised in Pensacola, Florida, specifically in the Northeast Pensacola section of Ferry Pass. She attended Ferry Pass Middle School and W.J. Woodham High School, graduating in 1981. Not many years after her graduation she appeared on Star Search as a contestant. She did not win, but the exposure led to her becoming a background singer for Steely Dan and small roles in several films.