Ashley Gearing made her chart debut in 2003 with the song "Can You Hear Me When I Talk to You?", which peaked at No. 36 on the U.S. BillboardHot Country Singles & Tracks charts. Eleven years old at the time, she became the youngest solo artist to enter the country charts, breaking a record held by Brenda Lee. "Can You Hear Me When I Talk to You?" was released as a single on Lyric Street Records. It was followed by "Ribbons of Love", which failed to chart. Neither single was included on an album.
Her first full length album, Maybe It's Time, was released on the independent label Squeeze Records in 2006. This album included the single "I Found It in You". In 2007, she moved to Curb Records, charting again with the single "Out the Window" in mid-2008. A second Curb single, "What You Think About Us," was given a release of July 2010.