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Caldwell first sang publicly at age five in beauty pageants.

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On June 18, 2011, Caldwell was crowned "Queen of Don't H8" at Nashville Pride, a title handed to her in honor of her work with the LGBT community.

On May 21, 2009 Caldwell announced she had just signed a record deal, and her debut album Without Regret would hit stores on April 6, 2010.

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In 1995, she sang at the 50th wedding anniversary of former President George H. Following her run on the second season of American Idol, Caldwell started working as a correspondent for the entertainment/extreme sports program 54321 on FOX Sports Network.

She covered various events and movie premieres for the show before joining her fellow Season 2 Idol finalists on the road for the American Idols LIVE!In December 2009, she released her first single "Mess of You" from her debut album which will be released through Vanguard/Capitol.On April 13, 2011 her debut album was released and it sold 3,000 copies its first week.David Cook says he’s dating an “American Idol” alum.The newly crowned “Idol” winner said Tuesday on “Live With Regis and Kelly” that he recently had a dinner date with former “Idol” contestant Kimberly Caldwell. When asked if he had a good time, Cook replied: “I did. So we’ll see.” Caldwell, 26, appeared on the second season of the top-rated Fox singing competition.She later announced that the album would be delayed until July due to the addition of new songs.

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