When she was 19,Pickler auditioned for American Idol in the fall of 2005 in Greensboro, North Carolina. The judges sent her to Hollywood and Pickler advanced through the semi-final rounds in February.
On March 9, she reached the Top 12. Pickler was among judge Simon Cowell's favorites. He once predicted Pickler would be in the final three, and said he preferred her over the previous season's winner, Carrie Underwood.
Recognized for her "quirky" personality and Southern charm, Pickler gained attention on the show by saying that she had hardly ever performed before real audiences, and by mispronouncing words. She was compared to Jessica Simpson in a March 27 story in US Weekly magazine titled "Kellie: The Next Jessica Simpson,” due to her "sweet Southern style and ditzy demeanor.” Pickler has stated several times that she was not heavily exposed to modern pop culture. She finished in sixth place.
In 2006, she signed to 19 Recordings and BNA Records as a recording artist, releasing her debut album, Small Town Girl, later that year. To date, it has sold over 800,000 copies. The album, which was certified gold by the RIAA, produced three singles on the Billboard Hot Country Songs charts: "Red High Heels" at number fifteen, "I Wonder" at number fourteen, and "Things That Never Cross a Man's Mind" at number sixteen.
She released her self-titled second album in Fall 2008 that spawned the singles "Don't You Know You're Beautiful" at number twenty-one, "Best Days of Your Life" at number nine (which she co-wrote with Taylor Swift and her first Top 10 hit), "Didn't You Know How Much I Loved You" at number fourteen, and "Makin' Me Fall in Love Again" at number thirty.
In 2008, she was nominated for "Top New Female Vocalist,” but the award went to Taylor Swift. She was also nominated for "New Artist Of The Year" at the CMA Awards for the second year in a row, but lost to Lady Antebellum. Pickler was nominated for "Female Video Of The Year" at the 2009 CMT Music Awards for "Don't You Know You're Beautiful.” She lost once again to Swift.
In June 2008, she joined friend Carrie Underwood, a long-time vegetarian, in giving up eating meat. In May 2009, it was announced that Pickler was nominated and won the title of "World's Sexiest Vegetarian" by PETA.
In 2012, she was ranked as the 14th best American Idol alumna.
On September 4, 2012, Pickler shaved her head on Good Morning America in support of her friend, Summer Holt Miller, who started chemotherapy after breast surgery. In October 2012, she signed with Black River Entertainment. On May 21, 2013, Pickler and her partner Derek Hough were declared the winners of sixteenth season of Dancing with the Stars.
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