In 1993, Keith went to Nashville, Tennessee. Keith hung out and busked on Music Row and at a place called Houndogs. He distributed copies of a demo tape the band had made to the many record companies in the city. There was no interest by any of the record labels and Keith returned home feeling depressed. Keith had promised himself to have a recording contract by the time he was 30 years old or give up on music as a career. He had already passed that age without any prospects for a recording contract.

Fortunately for Keith, a flight attendant and fan of his gave a copy of Keith's demo tape to Harold Shedd, a Mercury Records executive, while he was traveling on a flight she was working. Shedd enjoyed what he heard, went to see Keith perform live and then signed him to a recording contract with Mercury. His debut single, "Should've Been a Cowboy" (1993), went to number 1 on the Billboard country singles chart, and his self-titled debut album was certified platinum. Other hit sin