In 1986, the family returned to “civilization” so Bill and Diane could pick up interrupted music careers. First, Kasey joined them as lead singer, then Nash, and they became known as the Dead Ringer Band. By 1992, the family had become full-time musicians, playing to city audiences as well as heading back out into the countryside, pulling a small trailer behind their Toyota Land Cruiser.
During the 1990s, the Dead Ringer Band members, known as performers of quality country music, released seven CDs and collectively earned two ARIAs (Australian version of the Grammys) and seven Gold Guitars at the Australian Country Music awards in Tamworth. Kasey was the face of the new generation in Australian country. She appeared at Tamworth dressed as a spice girl, wore a nose ring and posed nude for a country music magazine, walking down the streets of a deserted country town with Nash.
In 1998, Chambers’ parents separated, with Diane choosing to live in distant Norfolk Island, two-and-a-half hours by plane off the Australian coast. Kasey started putting her feelings into songs, and over a few weeks during the summer of 1998, she recorded her solo album The Captain on Norfolk Island. With Nash as producer, she and her musicians set up in an old homestead on the island and practically recorded the album live. Bill played guitar and two of Kasey’s heroes, Buddy and Julie Miller, added voices and guitar to four tracks afterwards in Nashville.
Released in 1999, The Captain won the 1999 ARIA award for best country album. At the 2000 awards, she was named best female artist. With triple-platinum sales in Australia, she spent the latter part of 2000 following up enthusiastic reviews for her album internationally. She also toured the U.S. with Lucinda Williams and played gigs in her native land with Emmylou Harris. She was in the studio as well. With her brother Nash at the production board, Kasey Chambers delivered another sonic beauty with 2002’s Barricades and Brick Walls, with guests such as Williams and Buddy Miller. The album featured the smash hit “Not Pretty Enough” and ended up seven-times platinum.
In 2002, Kasey gave birth to a son, Talon. (Within a year or so, Nash and Bill also welcomed infant sons as well.) She released the album Wayward Angel in 2004. She still tours with her family, with Nash and Bill in her band, and Diane selling merchandise.