Starr's college stint was short-lived, for she packed her bags after three semesters in order to do music full-time. Her 1996 EP, Stupid Girl, reflected upon her time spent in school. A year later, Starr issued her proper mainstream debut, Eighteen Over Me, and exuded a new confidence and fresh musical direction. Her music was sultry, yet abrasive. She was coming into her own as an artist, but also as an individual. Such a change didn't last long, though, for Starr was a bit disenchanted with her life choices and faced self-doubts in her early twenties. Longtime friend and songwriter Clay Jones supported her throughout this period of second guessing.
After a move from Nashville to Los Angeles, Starr and Jones began writing songs together. Starr took her time with the new material. Featuring a post-alternative and country twist, Songs from Take Off to Landing, Starr's second effort, was issued in spring 2002. Starr made her Vanguard debut in 2004 with Airstreams Satellites. Within a year's time, Starr decided to leave Los Angeles for a return to the sunnier side of Nashville. She and her longtime collaborator, guitarist Neilson Hubbard, joined bassist/engineer Brad Jones for the production of Starr's fifth album. The Sound of You and Me, released in March 2006, was the most honest and emotional album of her career to date, though it was her next record, 2007's The Girl That Killed September, that the singer considered her "best." ~ MacKenzie Wilson, Rovi