With the release of their 1989 debut album Pickin' on Nashville via Mercury Records, the band charted four consecutive Top 40 country singles.

The label closed after Led Zeppelin drummer John Bonham died, and Itchy Brother never recorded a full album on Swan Song.

[1] The Kentucky Headhunters borrowed $4,500[9] 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.

[12][13] In addition, it earned a double-platinum certification from the Recording Industry Association of America (RIAA) for shipping two million copies in the United States.

[14] William Ruhlmann of Allmusic gave the album a four-and-a-half star rating out of five, saying that the band was "all the better" for having a sound closer to rock than country.

[11] The third and fourth singles were the original composition "It's Chitlin' Time" and a rendition of Waylon Jennings's "Only Daddy That'll Walk the Line," at numbers 63 and 60 respectively.

Alanna Nash of Entertainment Weekly gave it an A rating, saying that it "skillfully blends raw wit, the working-class energy of sweat-stained factory workers jamming between shifts, and musical styles as diverse as the corny Tennessee Ernie Ford and the creamy Eric Clapton.

"[21] Randy Lewis of the Los Angeles Times called the band "ZZ Top lite" and said that most of the songs on the album had a "party-hearty sound.

"[22] Later in 1991, The Kentucky Headhunters performed with Roy Rogers on the song "That's How the West Was Swung" from his Tribute album,[23] and covered Canned Heat's "Let's Work Together" for the soundtrack to the film Harley Davidson and the Marlboro Man.

sold poorly[3][28] and failed to produce a successful single among its three releases: "Honky Tonk Walkin' ," "Blue Moon of Kentucky" and "Dixie Fried," the latter two being covers of Bill Monroe and Carl Perkins, respectively.

"[30] Nash's review for Entertainment Weekly gave it a C− grade, and called it "warmed-over blues" that lacked the "outrageousness, wit, and brilliance that distinguished their earlier albums.

[35] Thom Owens of Allmusic wrote of this album that "They certainly can work a heavy, bluesy groove with dexterity, but they lack the gonzo charm they had on their debut, Pickin' on Nashville — there simply isn't the sense of careening fun, nor is there the reckless fusions that resulted in such an invigorating listen.

[38] In 1997, The Kentucky Headhunters signed to BNA Records to release its fourth non-collaborative studio album, Stompin' Grounds, with Doug on lead vocals.

[11][39] In order to promote the album, Richard suggested that the label send free copies to smaller-market radio stations, where the band's fanbase was still strong.

The band had consulted with 38 different independent labels before signing to Audium Entertainment, a branch of Koch Records (now MNRK Music Group), which released the album in 2000.

"[44] An uncredited review in The Ledger, which gave the album two-and-a-half stars out of four, said that the up-tempo songs were "nothing very original[…]but lots of fun" but added that its ballads were "mushy and earnest.

[47] Matt Bjorke of About.com considered its sound a departure from the earlier albums, but added "it's not hard to see that the band fully enjoys what they are doing" and highlighted the presence of a horn section and Hammond B-3 organ on some tracks.

[46] Ray Waddell of Billboard magazine considered Wynans' and Johnson's contributions "perfect fits", and noted that the album was "laid back" until the second half.

[50] Richard helped select the songs for this album, which included three other Hank Williams covers,[50] as well as Bob Dylan's "Like a Rolling Stone," The Beatles' "I'm Down," and Patsy Cline's "Walkin' After Midnight," among others.

[51] Despite saying that the album was "obviously aimed at longtime fans," Greg Prato of Allmusic gave it three-and-a-half stars, with his review making note of the "beefed-up" Patsy Cline and Hank Williams covers.

"[53] Robert Woolridge gave a mostly-favorable review for Country Standard Time, citing "Chug-a-Lug" and "So Sad to See Good Love Go Bad" (originally by The Everly Brothers) as the most country-sounding.

"[49] Kenney left the band around 2008 to take a job as the technical director of a theatre in Glasgow, Kentucky,[55] and Doug has since taken over on bass guitar.

The album features Jimmy Hall and Jeff Beck, plus appearances by members of The Kentucky Headhunters, Phil Keaggy, Darrell Mansfield (for whom Martin has previously played), and others.

[69] In 2009, Martin began a side project called Rufus Huff with Chris Hardesty, Dean Smith, and Jarrod England.

[70][71] Richard, along with Stan Webb and former MCA Nashville Records artist Marty Brown, wrote Tracy Byrd's 1998 single "I'm from the Country."

"[15] Lead singer Doug Phelps' voice has been described as "alternately suggest[ing] Count Basie's storied blues shouter Jimmy Rushing and the laid-back cool of Eagle Glenn Frey.

[77][78] The band's original compositions, such as "Dumas Walker" and the title track to Songs from the Grass String Ranch, often develop a regional theme.

[8] At their peak in the early 1990s, The Kentucky Headhunters were considered a dark horse in country music, due to the significant mainstream attention that the band received despite their rougher sound and the members's rural Southern image.

[10][79] In 1991, Entertainment Weekly critic Alanna Nash wrote that although the band did not sell as many albums as contemporaries George Strait or Garth Brooks, "they may just end up redefining country for the '90s" given the diverse range of influences and styles.

[20] Billboard critic Ray Waddell called the band "arguably the most consistent and durable Southern rock outfit on the planet.