In 1993, Toby Keith went to Nashville, Tennessee. Toby 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. Toby 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 Toby, a flight attendant and fan of his gave a copy of Toby'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 Toby 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 singles included "A Little Less Talk And A Lot More Action" and "Wish I Didn't Know Now".

Toby moved briefly to Polydor Records and released his next two albums, Boomtown (1994) and Blue Moon (1996). The albums went gold and platinum respectively. In 1996, Toby was also featured on the Beach Boys' now out-of-print 1996 album Stars and Stripes Vol. 1 performing a cover of their 1963 hit Be True to Your School with the Beach Boys themselves providing the harmonies and backing vocals.

Polydor folded and Toby moved back to Mercury Records (now called Mercury Nashville), and released his fourth album, Dream Walkin' (1997). The album featured a duet with Sting, "I'm So Happy I Can't Stop Crying", which had previously been a hit for Sting himself.