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On the schedule

The Highway Men Tour Dates & Tickets

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Inside the performance

Sound, stage & company

Onstage company

Documented collaborators

The Highway Men brought together four of country music's most influential voices in a groundbreaking collaboration that defined a genre for a decade. Active as a group from 1985 to 1995, with their distinctive blend of folk, country, and outlaw vibes, they left a lasting imprint on American roots music. Although Kris Kristofferson passed away in 2024 and the official group activity paused, 2025 features tribute performances that celebrate their legacy across select venues.

Onstage company

Documented collaborators

We’ve got you covered with reliable ticket access for both traditional releases and tribute shows, plus practical details on venues and how to secure seats for these modern tributes. This page pulls together the history, discography highlights, and upcoming tour info so you can plan your next listening and live experience around The Highway Men.

Onstage company

Documented collaborators

Who were The Highway Men? The Highway Men united Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson for a collaborative run that reshaped country music in the 1980s. Their debut, Highwayman (1985), topped the US country charts with the title track reaching No. 1 in 1985. The group followed with Highwayman 2 (1990) and The Road Goes on Forever (1995). A live album, Live: American Outlaws (1986), and several compilations—The Very Best of the Highwaymen (2016) and The Essential Highwaymen (2010)—kept their music alive for fans long after their peak. Awards include Grammy recognition for Best Country Song in 1986 for the title track “Highwayman,” awarded to the writers and performers involved, with Jimmy Webb contributing as the songwriter on the piece.

Onstage company

Documented collaborators

Today, 2025 tribute shows celebrate the group’s influence with lineups honoring the classic quartet. All shows listed are tribute performances and not the original act. For updates, follow Willie Nelson for connections to the broader family of artists and find venues near you hosting these tributes.

Onstage company

Documented collaborators

Social links for core members provide context for fans exploring related music: Willie Nelson's official brand pages offer ongoing tour info and releases at Instagram. Kris Kristofferson’s legacy continues through ongoing tributes and his broader discography, with information available via official pages and cultural outlets.

The essentials

Quick Facts About The Highway Men

  • Members: Johnny Cash, Waylon Jennings, Willie Nelson, Kris Kristofferson.
  • Active as a group from 1985 to 1995, with their fifth release style continuing into the late 1990s in compilations.
  • Studio albums: Highwayman (1985), Highwayman 2 (1990), The Road Goes on Forever (1995).
  • Hit single: Highwayman reached No. 1 on the US Country chart in 1985.
  • Awards: Jimmy Webb won the Grammy for Best Country Song in 1986 for the Highwaymen’s version of Highwayman.
  • The group also released a live album (Live: American Outlaws, 1986) and several compilations through 2016, including The Very Best of the Highwaymen (2016) and The Essential Highwaymen (2010).

The records

The Highway Men Discography

  • The Essential Highwaymen
    2010 · Columbia Nashville Legacy
  • The Very Best of the Highwaymen
    2016 · Sony Legacy
  • Live: American Outlaws
    2016 · Legacy Recordings
  • Highwayman
    1985 · Columbia
  • Highwayman 2
    1990 · Columbia
  • The Road Goes on Forever
    1995 · Liberty
  • Highwayman Super Hits
    1999 · Sbme Special Mkts./Sony

The hits

Top The Highway Men Songs

  • Silver Stallion
    1990 · US Country #25
  • Desperados Waiting for a Train
    1985 · US Country #15
  • Highwayman
    1985 · US Country #1

Who were The Highway Men? The Highway Men united Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson for a collaborative run that reshaped country music in the 1980s. Their debut, Highwayman (1985), topped the US country charts with the title track reaching No. 1 in 1985. The group followed with Highwayman 2 (1990) and The Road Goes on Forever (1995). A live album, Live: American Outlaws (1986), and several compilations—The Very Best of the Highwaymen (2016) and The Essential Highwaymen (2010)—kept their music alive for fans long after their peak. Awards include Grammy recognition for Best Country Song in 1986 for the title track “Highwayman,” awarded to the writers and performers involved, with Jimmy Webb contributing as the songwriter on the piece.

Today, 2025 tribute shows celebrate the group’s influence with lineups honoring the classic quartet. All shows listed are tribute performances and not the original act. For updates, follow Willie Nelson for connections to the broader family of artists and find venues near you hosting these tributes.

Social links for core members provide context for fans exploring related music: Willie Nelson's official brand pages offer ongoing tour info and releases at Instagram. Kris Kristofferson’s legacy continues through ongoing tributes and his broader discography, with information available via official pages and cultural outlets.

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