The Kentucky Headhunters created a hybrid of honky tonk, blues, and Southern rock that made them popular with fans of both rock and country music. The group's rowdy spirit belied their strong instrumental skills, and while they were marketed as a country act, their familiarity with blues and soul allowed them to transcend the genre, and over time they carved out a career path all their own. Their 1989 debut Pickin' on Nashville was a success that made their name, 1993's That'll Work was a collaboration with former Chuck Berry pianist Johnnie Johnson, 2003's Soul was a creative detour into vintage R&B styles, and 2021's That's a Fact, Jack! was a set of upbeat music meant to encourage fans during difficult times.

The origins of the Kentucky Headhunters lie in 1968, when Fred and Richard Young began playing together with their cousins Greg Martin and Anthony Kenney at the Youngs' grandmother's house. Mark Orr also later joined them. The first incarnation of the band was called the Itchy Brothers, and the group played together informally for over a decade. After about 13 years, the bandmembers began launching separate careers: Richard Young went off to write songs for Acuff-Rose, while Fred Young began touring with country beauty Sylvia. Martin became a member of Ronnie McDowell's band, while Kenney dropped out of music. In 1985, Martin decided to reassemble the Itchy Brothers. When Kenney declined to rejoin the group, Martin remembered Doug Phelps, whom he had met while on tour with McDowell. Phelps joined the new project, which was named the Kentucky Headhunters. Besides Martin and Phelps, the band also included the Young brothers and Doug's brother Ricky Lee Phelps.

The Headhunters started playing twice monthly on The Chitlin' Show, a program on Munfordville, Kentucky radio station WLOC. From these 90-minute performances, the Headhunters built up a following. They sent an eight-song demo to Mercury, and soon after, the label signed the group. The original demo tape was remixed, and became the basis of the band's first album, 1989's Pickin' on Nashville, which received overwhelmingly positive reviews upon its release and quickly became a hit. "Dumas Walker" reached number 15 in the spring of 1990, followed by the group's biggest hit, the number six "Oh, Lonesome Me." In 1991, the Headhunters released their second effort, Electric Barnyard. The album received mixed reviews, couldn't muster a single, and sold weakly. In summer 1992, the Phelps brothers left the group to form Brothers Phelps, a more traditional country group.

The remaining Headhunters brought ex-Itchy Brothers Anthony Kenney and Mark Orr to the group, and the rehashed lineup released Rave On! in 1993. The album marked a progression toward bluesy Southern rock, which came to fruition later that same year with That'll Work, a collaboration with former Chuck Berry pianist Johnnie Johnson. In 1996, Doug returned on lead vocals, and a year later the band issued Stompin' Grounds. Songs from the Grass String Ranch followed in 2000, and Soul appeared in spring 2003. Big Boss Man was released in 2005 and Flying Under the Radar in 2006, both from CBUJ Entertainment. Dixie Lullabies, the group's 12th album, and first studio recording of new original material since 2003, appeared from Red Dirt Records in 2011.

In 2015, the Headhunters released another collaborative album with Johnnie Johnson, Meet Me in Bluesland, drawn from unissued sessions recorded in 2003, two years before Johnson's death. Just before entering the studio to record their next studio LP, bandmates Richard and Fred Young lost their father. That loss, combined with the excitement of the band's first European tour, added an emotional poignancy to On Safari, which was released in 2016. The group's appearance at the Ramblin' Man Fair, a British music festival devoted to classic rock acts, was documented on the 2019 concert set Live at the Ramblin' Man Fair, which included three rare bonus studio tracks with Johnnie Johnson and Anthony Kenney. The Headhunters headed back into the studio for their next project, 2021's That's a Fact, Jack!, which contained 11 original songs from the group as well as their version of the Rick Derringer number "Cheap Tequila." ~ Johnny Loftus, Rovi