The Highwaymen (country supergroup)

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For the folk band, see The Highwaymen (folk band).
The Highwaymen
Background information
Also known as Nelson, Jennings, Cash, Kristofferson
Origin U.S.A.
Years active 19851995
Associated acts Jimmy Webb
Past members

The Highwaymen were a Country music supergroup composed of four of the genre's biggest artists well known for their pioneering influence on the outlaw country subgenre: Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson. Active between 1985 and 1995, these four artists 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 the years of 1997 and 1999, Nelson, Kristofferson, Cash, and Jennings also 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, only one recording vocal artist ever appeared on a Highwaymen recording: Johnny Rodriguez, who provided a Spanish vocal on 'Deportee', a Woody Guthrie cover, from "Highwayman".



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

Highwayman 2[edit]

In 1990, the group 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 prior to Jennings's death in 2002 was the 1995 Don Was-produced album The Road Goes on Forever, (a Robert Earl Keen cover), with the single, "It Is What It Is". The four singers then returned to their solo careers. 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 music video for "It Is What It Is" and a documentary entitled Live Forever – In the Studio with the Highwaymen.


Studio albums[edit]

Title Album details Peak chart positions Certifications
(sales threshold)
US Country
CAN Country
Highwayman 1 92 20
Highwayman 2
  • Release date: February 9, 1990
  • Label: Columbia Records
4 79 9
The Road Goes On Forever 42 10 46 8 11
"—" denotes releases that did not chart

Compilation albums[edit]

Year Album Label
1995 The Highwaymen Ride Again Columbia
1999 Super Hits
2005 Country Legends DeLuxe Holland
2010 The Essential Highwaymen Columbia


Year Single Peak chart positions Album
US Country
CAN Country
1985 "Highwayman" 1 1 19 98 Highwayman
"Desperados Waiting for a Train" 15 20
1990 "Silver Stallion" 25 21 Highwayman 2
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


Music videos[edit]

Year Title Director
1985 "Highwayman" Peter Israelson
1990 "Silver Stallion" Jon Small
1995 "It Is What It Is" Lowe/Don Was

Video albums[edit]

External links[edit]