Keith graduated from Moore High School and, in 1979, went to work as a derrick hand in the booming oil fields of Oklahoma. He worked his way up to become an operation manager. At the age of 20, he formed the Easy Money band and they played local bars as he continued to work in the oil industry. At times, he would have to leave in the middle of a gig if he was paged to work in the oil field.

In 1982, the oil industry in Oklahoma began a rapid decline and Keith soon found himself unemployed. He fell back on his football training and played defensive end with the Oklahoma City Drillers of the United States Football League (USFL) for two years while continuing to perform with his band. When the USFL suspended operations, Keith decided to try music full time. His family and friends were doubtful he would succeed but in 1984, Easy Money began playing the honky tonk circuit in Oklahoma and Texas. The band cut a single titled "Blue Moon" and the song received some airplay on local radio stations in Oklahoma.

In 1993, Keith went to Nashville, Tennessee. 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 was approaching that age without any prospects for a recording contract.

Fortunately for Keith, a fan of his, who was a flight attendant, 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 liked 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.

Keith moved briefly to Polydor Records and released his next two albums Boomtown (1994) and Blue Moon (1996). The albums went gold and platinum respectively. Polydor folded and Keith moved back to Mercury Records, now called Mercury Nashville, and released his fourth album, Dream Walkin' (1997).

He began work on his next album How Do You Like Me Now (1999) at Mercury but purchased the rights to the album and moved to Dreamworks Nashville because of creative differences with Mercury. The title song, "How Do You Like Me Now," was a number 1 single for 5 weeks and the album went double platinum.

Keith also began doing a series of television advertisements for Telecom USA for their discount long distance telephone service 10-10-220. Because of the ads and his latest hit album, Keith became a superstar and household name.

On March 24, 2001, Keith’s father, H.K. Covel, was killed in a car accident. That event and the September 11, 2001 attacks prompted Keith to write the song "Courtesy of the Red, White and Blue (The Angry American)," a song about his father’s patriotism and faith in the USA. At first, Keith refused to record the song and only sang it live at his concerts for military personnel. The reaction was so strong that the Commandant of the Marine Corps James L. Jones told Keith it was his duty to record the song. As the lead single from the album Unleashed (2002), "Courtesy of the Red, White and Blue" peaked at number 1 over the weekend of July 4. The album spent 65 weeks on the top-10 Billboard Country Albums chart.

ABC invited Keith to sing "Courtesy of the Red, White and Blue" on a patriotic special it was producing. However, the host of the show, newsman Peter Jennings, requested Keith soften the lyrics of the song or choose another song to sing. Keith refused both requests and did not appear on the special. The rift gave the song an extreme amount of publicity, which led to many national interviews and public performances of the song. Keith also had a public feud with the Dixie Chicks over the song. The lead singer of the Dixie Chicks, Natalie Maines, publicly stated that the song was "ignorant, and it makes country music sound ignorant." Keith defeated the Dixie Chicks to win Entertainer of The Year from the Academy of Country Music (2002).

Keith was the subject of the January 2005 issue of Playboy Magazine's Playboy Interview. Keith's 2005 plans include a tour with rock guitarist Ted Nugent, whom Keith met in Iraq while they were both performing in USO-sponsored shows for the coalition troops.

Discography
Toby Keith (1993)
Boomtown (1994)
Christmas To Christmas (1995)
Blue Moon (1996)
Dream Walkin' (1997)
Greatest Hits Volume 1 (1998)
How Do You Like Me Now (1999)
Pull My Chain (2001)
Unleashed (2002)
20th Century Masters: The Millennium Collection... (2003)
Shock'n Y'all (2003)
Greatest Hits Volume 2 (2004)

Notable Awards
Academy of Country Music - Album of the Year (2000) How Do You Like Me Now
Country Music Association (CMA) - Male Vocalist of the Year (2001)
Academy of Country Music - Entertainer of the Year (2002)
Academy of Country Music - Entertainer of the Year (2003)
Academy of Country Music - Top Male Vocalist (2003)
Academy of Country Music - Album of the Year (2003) Shock'n Y'all
Academy of Country Music - Video of the Year (2003) Beer For My Horses (with Willie Nelson)