The Highwaymen were an American supergroup of country music artists. The group consisted of Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson. Between 1985 and 1995, they 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.
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 together in the 1986 film Stagecoach.
Glen Campbell, who recorded the song in 1978 as part of his 1979 album Highwayman, did not appear on any recording but temporarily joined the supergroup in a 1985 live performance at the first Farm Aid concert in Kristofferson's absence. Campbell was also a friend to each individual member, and played in early sessions with them.https://www.rollingstone.com/music/music-features/the-highwaymen-the-fights-and-friendship-of-countrys-great-supergroup-184126/
In 1990, the original members of the 1950s-'60s folk group of the same name sued the Highwaymen over their use of the name, which was inspired by a Jimmy Webb ballad the country stars had recorded. The suit was dropped when all parties agreed that the folk group owned the name but that the earlier group would grant a nonexclusive, nontransferable license to the supergroup to use the name. The two groups shared the stage at a 1990 concert in Hollywood.
Albums Highwayman 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 In 1990, the four 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 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.
Final years: Breakup, aftermath, and occasional partial reunions
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 another country supergroup, Old Dogs; Jennings died in 2002, and Cash died in 2003.
Nelson and Kristofferson collaborated on multiple occasions following the deaths of Jennings and Cash, but they were not credited as the Highwaymen for these occasions. For example, in November 2003, Nelson and Kristofferson reunited to perform "Big River", one of Cash's songs that he had re-recorded in 1985 with his Highwaymen bandmates, with George Jones at a Grand Ole Opry-sponsored memorial concert for Cash at the Ryman Auditorium in Nashville, Tennessee.
"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."Bell, Max: "Q&A: Kris Kristofferson"; Classic Rock #148, August 2010, p34
In 2012, Kristofferson, Jamey Johnson, and Snoop Dogg collaborated with Nelson on the single "Roll Me Up and Smoke Me When I Die".
In 2016, Nelson and Kristofferson recorded a virtual collaboration of “One Too Many Mornings”, featuring archived vocals by Cash and Jennings recorded during the 1980s. This was released as a bonus track on the 2016 live album “Live: American Outlaws,” recorded at Nassau Coliseum in 1990.
Kristofferson died on September 28, 2024, leaving Nelson as the last living member of the Highwaymen.
Discography Studio albums Title Album details Peak chart positions Certifications(sales threshold) US Country US AUSAustralian chart peaks: Top 100 (Kent Music Report) peaks to 12 June 1988: 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: CAN Country DEN NOR Highwayman Release date: May 6, 1985 Label: Columbia Records 1 92 23 — — — AUS: Platinum US: Platinum CAN: Gold Highwayman 2 Release date: February 9, 1990 Label: Columbia Records 4 79 9 — — — AUS: Platinum The Road Goes On Forever Release date: April 4, 1995 Label: Liberty Records 42 — 46 10 8 11 "—" denotes releases that did not chart
Compilation albums Title Album details Peak positions Sales US Country AUS The Highwaymen Ride Again 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 Release date: May 20, 2016 Label: Legacy Recordings 16 89US: 12,500 The Very Best of the Highwaymen Release date: May 20, 2016 Label: Legacy Recordings 22 —US: 48,900 "—" denotes releases that did not chart
Singles Year Single Peak chart positionsCertifications Album US Country AUS CAN Country CAN AC 1985 "Highwayman" 1 98 1 19BPI: Silver RMNZ: Gold Highwayman "Desperados Waiting for a Train" 15 — 20 — 1990 "Silver Stallion" 25 123 21 — Highwayman 2 "Born and Raised in Black and White" —A — — — "American Remains" — — — — 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
Notes: 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.
Videography Music videos 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" Jon Small
Video albums Year Title Details Certification 1991 Highwaymen Live! filmed in 1990 at the Nassau Coliseum AUS: 10× Platinum 1993 On the Road Again filmed in 1992 in Aberdeen, Scotland 2016 The Highwaymen Live at The Nassau Coliseum filmed in 1990 at the Nassau Coliseum An extended re-edit of Highwaymen Live! AUS: Gold
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