Kellie Pickler was 19 when she auditioned for American Idol in its fifth season. She was one of judge Simon Cowell’s favorite contestants due to not only her talent, but her innocence and small town ways. The sweet Southern country singer came in sixth place on the show and has since released four albums. Her first one, “Small Town Girl,” went gold. Kellie, now 28, won the 16th season of Dancing with the Stars in 2013 with her partner Derek Hough and made a guest appearance on 90210 in 2011 in the role of Sally Butler.