Kellie Pickler Pictures Collection. Kellie Dawn Pickler (born June 28, 1986) is an American country music artist and television personality. She gained fame as a contestant on the fifth season of the Fox reality show American Idol, eventually finishing 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 and has produced 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 2012, she was ranked as the 14th best American Idol alumna. She also parted ways with her former record label. On October 2012 she signed with Black River Entertainment.