With her life back together, she started a band, Tragic Sam, and produced a few sessions with Billy Rush, the former guitarist for Southside Johnny & The Asbury Jukes. She moved to New York City around 1992 and tried forming a few ensemble groups, without much success. She began waiting tables, while living with then-boyfriend Karl Anderson in one bedroom apartment. She devoted whatever free time she had to her music. Realizing, New York City was taking its toll on her, she and Anderson, the two now married optedmore

With her life back together, she started a band, Tragic Sam, and produced a few sessions with Billy Rush, the former guitarist for Southside Johnny & The Asbury Jukes. She moved to New York City around 1992 and tried forming a few ensemble groups, without much success. She began waiting tables, while living with then-boyfriend Karl Anderson in one bedroom apartment. She devoted whatever free time she had to her music. Realizing, New York City was taking its toll on her, she and Anderson, the two now married opted to move to Texas, hoping for a fresh start. Once in Austin, she played many open mic nights and would often busk on Sixth Street. She signed a deal with the Dallas-based indie label, Carpe Diem and began recording her debut album Anchorless. The album, which was produced by Dave McNair, was recorded with several local musicians. After performing at South By Southwest, Kacy signed a deal with Atlantic Records, which brought her music to a wider audience. The label released Anchorless in 1997, including two new tracks on this release. The album received some critical praise from publications such as Billboard, Vanity Fair and USA Today, but many of the critics had a lukewarm response to the record. Despite the response from critics, her songs were featured in films such as Anywhere But Here and Three to Tango She went out on tour in support of the record, playing at Lilith Fair and the H.O.R.D.E. festival and opening for artists Chantal Kreviazuk and Marc Cohn. She went into the studio in 2001 and recorded her second album Boys in the Attic which was shelved by Atlantic. Kacy soon parted ways with Atlantic and took some time off. She spent the next few years writing and found time to record her third album Moodswing. Released in 2003, the album quickly became a favorite in the Austin area. She released another album entitled Tramps Like Us in 2004.