Richard Young, his younger brother Fred, and their cousins Anthony Kenney and Greg Martin began performing music in the Youngs' 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 band achieved regional success in Kentucky in the 1970s, including at least one single, "Shotgun Effie," which they wrote about the Youngs' grandmother, Effie. It was released in 1973 on the King Fargo label. 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 its 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.
When Martin attempted to reunite Itchy Brother in 1985, the Young brothers joined him, but Kenney declined. 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 and play harmonica.
The band decided to name itself 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' debut album, Pickin' on Nashville. It produced four singles, all of which reached top 40 on the Billboard Hot Country Singles & Tracks (now Hot Country Songs) chart, and the rest is history...