Chambers recorded her debut solo album, "The Captain", on Norfolk Island during July and August 1998 with her brother Nash producing and father Bill on guitar. United States country musicians, Buddy and Julie Miller added guitars and vocals to four tracks. "The Captain" was released in May 1999 via EMI Music Australia and in June 2000 in the US by Asylum Records. It peaked at No. 11 on the ARIA Albums Chart and No. 1 on the related ARIA Country Albums chart. At the ARIA Music Awards of 1999 she won Best Country Album and in the following year she won Best Female Artist for its title track, which was issued in 2000.