The Highwaymen (country supergroup)

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The Highwaymen
Also known asNelson, Jennings, Cash, Kristofferson
OriginUnited States
Years active1985–1995
Associated actsJimmy Webb
Past members

The Highwaymen was an American country music supergroup, composed of four of country music's biggest artists who pioneered the outlaw country subgenre: Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson. Between 1985 and 1995, the group recorded three major label albums as The Highwaymen: two on Columbia Records and one for Liberty Records. Their Columbia works produced three chart singles, including the number one "Highwayman" in 1985.

Between 1996 and 1999, Nelson, Kristofferson, Cash, and Jennings provided the voice and dramatization for the Louis L'Amour Collection, a four-CD box set of seven Louis L'Amour stories published by the HighBridge Company, although the four were not credited as "The Highwaymen" in this work.

Besides the four formal members of the group, one other vocal artist appeared on a Highwaymen recording: Johnny Rodriguez, who provided Spanish vocal on "Deportee", a Woody Guthrie composition, from the album Highwayman.

The four starred in one movie together: the 1986 film Stagecoach.



Formed in 1985, the group did not have an official name when they released their first two albums on Columbia Records. The first album, Highwayman, was credited to "Nelson, Jennings, Cash, Kristofferson". The single "Highwayman", a Jimmy Webb composition, became a #1 country hit. Their cover of Guy Clark's "Desperados Waiting for a Train" reached the Top 20. The album was produced by Chips Moman.

Highwayman 2[edit]

In 1990, the 4 members reunited for a second effort, titled Highwayman 2, which reached #4 on the country album chart. The Lee Clayton-penned song "Silver Stallion" was the first single and made the country Top 40. The album was nominated for a Grammy for Best Country Vocal Collaboration. Highwayman 2 was produced, once again, by Moman. Six of the songs were written or co-written by members of the group.

The Road Goes on Forever[edit]

The group's final release (now listed as "Highwaymen") prior to Jennings's death in 2002 was 1995's Don Was-produced album The Road Goes on Forever, (a Robert Earl Keen cover), with the single, "It Is What It Is". A tenth-anniversary edition of The Road Goes on Forever appeared in 2005, with several bonus tracks added as well as, in some versions, a DVD containing the video for "It Is What It Is" and a documentary titled Live Forever – In the Studio with the Highwaymen.

The band continued to tour into the late 1990s, before Jennings and Cash both started to decline in health, which prevented them from maintaining a full touring schedule. All four continued to perform as solo artists, with Jennings briefly joining Old Dogs; Jennings died in 2002 and Cash died in 2003.

"Those tours and the records we made were a great time," recalled Kristofferson in 2010. "I just wish I was more aware of how lucky I was to share a stage with those people. I had no idea that two of them would be done so soon. Hell, I was up there and I had all my heroes with me. These are guys whose ashtrays I used to clean. I'm kinda amazed I wasn't more amazed."[1]


Studio albums[edit]

Title Album details Peak chart positions Certifications
(sales threshold)
US Country
CAN Country
Highwayman 1 92 23
Highwayman 2
  • Release date: February 9, 1990
  • Label: Columbia Records
4 79 9
The Road Goes On Forever 42 46 10 8 11
"—" denotes releases that did not chart

Compilation albums[edit]

Title Album details Peak positions Sales
US Country
The Highwaymen Ride Again
(Import Only - Greece & Netherlands)
  • Release date: June 11, 1995
  • Label: Columbia Records
Highwayman Super Hits
  • Release date: March 2, 1999
  • Label: Columbia Records
Country Legends
  • Release date: 2005
  • Label: DeLuxe Holland
The Essential Highwaymen
  • Release date: October 26, 2010
  • Label: Columbia Records
Live: American Outlaws 16 89
The Very Best of the Highwaymen
  • Release date: May 20, 2016
  • Label: Legacy Recordings
"—" denotes releases that did not chart


Year Single Peak chart positions Album
US Country
AUS[4] CAN Country
1985 "Highwayman" 1 98 1 19 Highwayman
"Desperados Waiting for a Train" 15 20
1990 "Silver Stallion" 25 21 Highwayman 2
"Born and Raised in Black and White" A
"American Remains"[13]
1995 "It Is What It Is" The Road Goes on Forever
2005 "If He Came Back Again" The Road Goes on Forever (re-issue)
"—" denotes releases that did not chart


  • A "Born and Raised in Black and White" did not chart on Hot Country Songs, but peaked at No. 1 on Hot Country Radio Breakouts.[14]


Music videos[edit]

Year Title Director
1985 "Highwayman" Peter Israelson
1990 "Silver Stallion" Jon Small
1995 "It Is What It Is" Lowe/Don Was
2016 "Good Hearted Woman"[15] Jon Small

Video albums[edit]

  • Highwaymen Live! (filmed in 1990 at the Nassau Coliseum, released in 1991 on VHS)
  • On the Road Again (filmed in 1992 in Aberdeen, Scotland, released in 2003 on DVD)
  • The Highwaymen Live: American Outlaws (A re-release of the full 1990 Nassau Coliseum concert, remastered from the original 16mm film and released in 2016 on DVD and Blu-ray)[16]

See also[edit]


  1. ^ Bell, Max: "Q&A: Kris Kristofferson"; Classic Rock #148, August 2010, p34
  2. ^ a b "The Highwaymen Album & Song Chart History – Country Albums". Billboard. Prometheus Global Media. Retrieved December 11, 2010.
  3. ^ "The Highwaymen Album & Song Chart History – Billboard 200". Billboard. Prometheus Global Media. Retrieved December 11, 2010.
  4. ^ a b c Australian chart peaks:
    • Top 100 (Kent Music Report) peaks to 12 June 1988: Kent, David (1993). Australian Chart Book 1970–1992 (Illustrated ed.). St Ives, N.S.W.: Australian Chart Book. p. 214. ISBN 0-646-11917-6. N.B. The Kent Report chart was licensed by ARIA between mid-1983 and 12 June 1988.
    • Top 100 (ARIA) peaks from January 1990 to December 2010: Ryan, Gavin (2011). Australia's Music Charts 1988–2010 (pdf ed.). Mt. Martha, VIC, Australia: Moonlight Publishing.
  5. ^ "Results – RPM – Library and Archives Canada – Country Albums". RPM. Retrieved December 11, 2010.
  6. ^ "RIAA – Gold & Platinum – December 26, 2010: The Highwaymen certified albums". Recording Industry Association of America. Retrieved December 26, 2010.
  7. ^ Ryan, Gavin (June 11, 2016). "ARIA Albums: Jimmy Barnes 'Soul Searchin' Is His 11th No 1 Album". Noise11. Retrieved June 11, 2016.
  8. ^ Bjorke, Matt (July 25, 2016). "Top 10 Country Albums Chart: Top 10 Country Albums Chart: July 25, 2016, 2016". Roughstock.
  9. ^ Bjorke, Matt (October 9, 2019). "Top Country Catalog Album Sales: October 9, 2019". RoughStock. Retrieved October 13, 2019.
  10. ^ "The Highwaymen Album & Song Chart History – Country Songs". Billboard. Prometheus Global Media. Retrieved December 11, 2010.
  11. ^ "Results – RPM – Library and Archives Canada – Country Singles". RPM. Retrieved December 11, 2010.
  12. ^ "Results – RPM – Library and Archives Canada – Adult Contemporary". RPM. Retrieved December 11, 2010.
  13. ^ "Single Reviews" (PDF). Billboard. September 29, 1990.
  14. ^ "Hot Country Radio Breakouts" (PDF). Billboard. June 30, 1990.
  15. ^ Stephens, Samantha (May 3, 2016). "World Premiere: The Highwaymen's "Good Hearted Woman"". Country Music Television. Retrieved May 5, 2016.
  16. ^ "The Highwaymen Live - American Outlaws Blu-ray".

External links[edit]