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Born Toby Keith Covel in Clinton, Oklahoma, Toby Kieth's family moved to Oklahoma City when Keith was young. It was there he became interested in the musicians who worked in his grandmother's supper club. His first guitar came at age 8, but it would be years before Keith would pursue music as a career. At 6-foot, 4 inches, Keith took a few detours, working in the oil industry and playing defensive end with the Oklahoma City Drillers United States Football League (USFL) team.

In 1984, Keith turned to music full time, playing the honky-tonk circuit in Oklahoma and Texas for several years. The budding singer-songwriter eventually was discovered by Mercury Records President Harold Shedd, a producer who worked with supergroup Alabama. After catching a show in Oklahoma, Shedd signed Keith to Mercury Records. His 1993 debut single, "Should've Been a Cowboy," went to No. 1 on the Billboard country singles chart, and his self-titled debut album was certified platinum.

When Shedd left Mercury for Polydor Records, Keith went with him. He released a second album, Boomtown, in 1994. The collection produced the No. 1 hit "Who's That Man" and the Top 5 hit "You Ain't Much Fun." The platinum-selling Blue Moon followed in 1996, featuring a more introspective Keith on tunes like "Does That Blue Moon Ever Shine on You" and the charttopper, "Me Too."

When Polydor closed its Nashville operation, Keith moved back to Mercury Nashville, releasing Dream Walkin' in 1997. The bittersweet ballad, "When We Were in Love," went to No. 2, as did a cover version of rocker Sting's divorce ode "I'm So Happy I Can't Stop Crying." The duet earned the unlikely pair a Grammy nomination, and Sting joined Keith for a performance on the 1997 Country Music Association Awards.

The platinum-selling Toby Keith: Vol. 1-Greatest Hits followed in 1998, which included a new cut called "Getcha Some." The sassy tune, co-written by Keith and frequent collaborator Chuck Cannon, only went to No. 18 on the Billboard country charts, but it drove sales of the collection. Signing with yet another record label, Keith moved to the fledgling DreamWorks Nashville in 1999. There he worked with label head and producer James Stroud on the new studio album How Do You Like Me Now?! The lead single, "When Love Fades," was a modest hit, but the title cut struck a nerve with country fans. "How Do You Like Me Now?!" was a five-week No. 1 hit and helped the album sell platinum. The subsequent single, "You Shouldn't Kiss Me Like This," also went to the top spot on the singles chart.

The success of How Do You Like Me Now?! also earned Keith some long-awaited award nominations within the music industry. Although his debut single went to No. 1 and his debut album sold platinum, Keith was overlooked for the newcomer awards at both the Academy of Country Music and the CMA. In 2001, Keith's name was included in six different categories for the 36th Annual ACM Awards, including single, song, video, album, male vocalist and entertainer.