Pickler gained fame as a contestant on the fifth season of American Idol and finished in sixth place. In 2006, she signed to 19 Recordings and BNA Records as a recording artist. Her debut album, Small Town Girl, was released later that year and has sold over 900,000 copies. The album, which was certified gold by the RIAA, produced three singles on the Billboard Hot Country Songs charts: "Red High Heels" at #15, "I Wonder" at #14, and "Things That Never Cross a Man's Mind" at #16.
Pickler released her self-titled second album in 2008 that produced four singles: "Don't You Know You're Beautiful" at #21, "Best Days of Your Life" at #9 (which she co-wrote with Taylor Swift), "Didn't You Know How Much I Loved You" at #14, and "Makin' Me Fall in Love Again" at #30.
In September 2017, she began to host a daytime talk show, Pickler & Ben with comedian Ben Aaron for E.W. Scripps, which currently airs exclusively on that chain's stations and CMT; the show is produced out of Scripps' Nashville station, WTVF.