Troy Cassar-Daley was born in Grafton, NSW. He first visited Australia's Country Music Festival at Tamworth as an 11-year-old boy, and was so captivated by the experience that he returned to the Festival a year later as a busker. By 16 he was touring Northern NSW with his band Little Eagle. His debut solo EP, Dream Out Loud, came out in 1994, and its title track reached Number One on Australia's country charts. His first LP, Beyond the Dancing, appeared the following year, winning him an ARIA for Best Country Record. In 1996 he won the Male Vocalist of the Year award at the Tamworth Country Music Awards. In June 1996, along with such fellow country stars as Lee Kernaghan and Gina Jeffreys, he performed at the Australian Country Music Showcase in Nashville, and later that year recorded the album True Believer in the US. In 1999 he released his third album, Big River. His fourth, Long Way Home, followed in 2002.