Keith was born in Clinton, Oklahoma, to Carolyn Joan (nee Ross) and Hubert K. Covel, Jr. and is of English ancestry. He has a sister and a brother. The family lived in Fort Smith, Arkansas, for a few years when Keith was in grade school, but moved to Moore, Oklahoma (a suburb of Oklahoma City) when he was still young. Before the family moved to Moore, he visited his grandmother in Fort Smith during the summers.
1996-98: Blue Moon, Dream Walkin', and Greatest Hits Volume One
Keith was moved to the short-lived Nashville division of A&M Records to release Blue Moon in April 1996. His third album to achieve a platinum certification, it also included three singles. The first was "Does That Blue Moon Ever Shine on You", written by Keith in 1987, which reached number 2. Following it were "A Woman's Touch" at number 6, and his third number 1 hit, "Me Too", which peaked in March 1997. Keith also appeared 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.  Following a corporate merger, Keith returned to Mercury in 1997. His fourth studio album, Dream Walkin', was also his first produced by James Stroud, who would also serve as Keith's co-producer until 2005. It produced two consecutive number 2 hits in "We Were in Love" and a cover of Sting's 1996 single "I'm So Happy I Can't Stop Crying". Sting also sang duet vocals and played bass guitar on it, and the two also performed the song at the 1997 Country Music Association awards. After this song, the album's title track made number 5, while "Double Wide Paradise" peaked at number 40.  Keith's last Mercury release was Greatest Hits Volume One in October 1998. The album included twelve of his prior singles and two new songs: the country rap "Getcha Some" and "If a Man Answers". Both were released as singles, with "Getcha Some" reaching top 20, but "If a Man Answers" became his first single to miss top 40. According to Keith, these two songs were originally to be put on a studio album, but Mercury executives, dissatisfied with the album that Keith had made, chose to put those two songs on a greatest hits package, and asked him to "go work on another album". After he recorded two more songs which the label also rejected, he asked to terminate his contract with the label. After exiting Mercury, Keith co-wrote Shane Minor's debut single "Slave to the Habit" with Chuck Cannon and Kostas.

Q: Were there any hit songs on Blue Moon?
A: Does That Blue Moon Ever Shine on You",

Q: So, "Does That Blue Moon Ever Shine On You" was not a commercial success--did it chart at all?
A: His third album to achieve a platinum certification,
How did Blue Moon do in other countries?
". After he recorded two more songs which the label also rejected, he asked to terminate his contract with the label.
". After he recorded two more songs which the label also rejected, he asked to terminate his contract with the label.