The Kentucky Headhunters are an American country rock and Southern rock band from Edmonton, Kentucky. The band's members are Doug Phelps (bass guitar, vocals), Greg Martin (lead guitar, vocals), and brothers Richard Young (rhythm guitar, vocals) and Fred Young (drums, vocals). Martin and the Young brothers began performing in 1968 as Itchy Brother, a group which also included Anthony Kenney on bass guitar and vocals. Itchy Brother performed until 1982, with James Harrison replacing Martin from 1973 to 1976. The Youngs and Martin began performing as The Kentucky Headhunters in 1986, adding brothers Ricky Lee Phelps (lead vocals, harmonica) and Doug Phelps (bass guitar, vocals) to the membership.

With the release of their 1989 debut album Pickin' on Nashville via Mercury Records, the band charted four consecutive Top 40 country singles. A second album for Mercury, Electric Barnyard, did not do as well commercially, and the Phelps brothers left after its release to form Brother Phelps. Kenney re-joined and Mark S. Orr took over on lead vocals for 1993's Rave On!! and a compilation album entitled The Best of The Kentucky Headhunters: Still Pickin' before the band exited Mercury. Orr left and Doug Phelps rejoined in 1996 as lead vocalist for the album Stompin' Grounds. He also led on the Audium Entertainment albums Songs from the Grass String Ranch and Soul, as well as Big Boss Man and a second compilation, Flying Under the Radar, on CBuJ Entertainment. After Kenney's departure, Doug once again became the band's bass guitarist by the release of Dixie Lullabies, in 2011.

The Kentucky Headhunters have released ten studio albums, three compilations, and twenty-three singles. Their highest-peaking single is a cover of the Don Gibson song "Oh Lonesome Me," which the band took to number eight on the Billboard Hot Country Songs charts in 1990. In addition, the band has won three Country Music Association awards, an Academy of Country Music award, and a Grammy Award for Best Country Performance by a Duo or Group with Vocal, won in 1990 for Pickin' on Nashville.

Richard Young, his younger brother Fred Young, and their cousins Anthony Kenney and Greg Martin began performing music in the Youngs's and Kenney's hometown of Glasgow, Kentucky, in the 1960s.They founded a band called Itchy Brother, named after Fred's favorite cartoon character, from King Leonardo and His Short Subjects. The original lineup consisted of Richard Young on rhythm guitar, Fred Young on drums, Kenney on bass guitar, and Martin on lead guitar. Itchy Brother achieved regional success in Kentucky in the 1970s, including at least one single, "Shotgun Effie," which they wrote about the Youngs'a grandmother, Effie. It was released in 1973 on the King Fargo label. That same year, Greg Martin left the group to play in another band in his hometown of Louisville, Kentucky. In the meantime, guitarist James Harrison took his place. Martin returned to the group in 1976.

Itchy Brother was almost signed to Swan Song Records, an independent label founded by the band Led Zeppelin, in 1980. The label closed after Led Zeppelin drummer John Bonham died, and Itchy Brother never recorded a full album on Swan Song. Itchy Brother broke up in 1982. After their disbanding, Richard started writing songs for Acuff-Rose Music, and Fred became a backing musician for country singer Sylvia, who at the time was recording on RCA Records. Martin played bass guitar and sang backing vocals for Ronnie McDowell, then a recording artist for Curb Records, and Kenney stopped performing, although he continued to write songs with the Young brothers.

Martin reuinted with the Young brothers in 1986. As Kenney declined to join the three, Martin invited Missouri Bootheel native Doug Phelps, also a member of McDowell's band, to replace Kenney, and Doug brought his older brother Ricky Lee to sing lead vocals. The band decided to name themselves The Headhunters, taking the name from the term "headchopper," which blues musician Muddy Waters used to indicate that he had supplanted another band in a gig. After discovering that other bands existed with that name, the band added "Kentucky" to its name and thus became The Kentucky Headhunters. The Kentucky Headhunters began performing together the following year, playing twice monthly on the 90-minute Chitlin' Show, a radio program on WLOC in Munfordville, Kentucky.

The Kentucky Headhunters borrowed $4,500 to record a demo album, which included seven original songs, plus covers of Bill Monroe's "Walk Softly on This Heart of Mine," Henson Cargill's "Skip a Rope", and Don Gibson's "Oh Lonesome Me." Originally intended to be sold at the band's live shows, the demo tape came to the attention of the Nashville music community. Although Martin said that the band had not seriously considered signing a record deal, the band pursued one through the suggestion of its manager, Mitchell Fox. Harold Shedd, a record producer who was then the head of Mercury Records, helped sign The Kentucky Headhunters to the label in 1989.

Mercury released the demo in 1989 as The Kentucky Headhunters's debut album, Pickin' on Nashville. The album produced four singles, all of which reached top 40 on the Billboard Hot Country Singles & Tracks (now Hot Country Songs) chart. The first of these, the "Walk Softly on This Heart of Mine" cover, peaked at number 25 in December 1989. After it came "Dumas Walker." According to Doug, Mercury Records was initially reluctant to release the song as a single: "[The label] thought it was too regional, and that no one outside the area would get it, but what they didn't see, was the reaction we got to it every night that we played it in front of a crowd, and it didn't matter where we were playing either." The single peaked at number 15 on the Billboard chart.