From the age of 9 to 14, Dexter was a lead singer in the four piece band Tristar who played live all over the Detroit area and neighboring cities.[4][7] She began singing background for other artists at age 11,[3] most notably for Simply Red.[2][3] At age 13 she signed to Elektra Records,[2] but an album on the label never materialized. Dexter signed to Warner Bros. Records in 1998 in her late teens,[2] and she released her eponymous debut album and two singles from the album,"Better Than Me" and "Strayed Away" in 1999 (although her debut single, "You'll Never Miss Me ('Til I'm Gone)" featured on the "Rush Hour" film soundtrack was released via Warner Bros. subsidiary Reprise Records).[8][9] She then moved to A&M Records and was featured on the single "Magic" alongside 'The Black Eyes Peas' as part of the "Legally Blonde" soundtrack but left the label without having released an album.[2] Dexter's critically acclaimed second album, Listen, spanned two singles and was released via Penny's Gang Records/Universal in 2008.[8]
