Caldwell first sang publicly at age five in beauty pageants. She was a five-time junior vocalist winner on Star Search, and she also performed at the Grand Ole Opry. In 1995, she sang at the 50th wedding anniversary of former President George H. W. Bush and Barbara Bush. Caldwell also appeared on the second and final season of Popstars: USA, where she was rejected from the group and told she would do better as a solo vocalist.
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