Waylon Jennings, Willie Nelson, Johnny Cash, Kris Kristofferson – Highwayman

The Highwaymen – Highwayman

A landmark collaboration in outlaw country, Highwayman brings together four of the genre’s most iconic voices: Johnny Cash, Willie Nelson, Waylon Jennings and Kris Kristofferson. Released in 1985, the album captures the spirit of American outlaw country through storytelling, shared vocal presence and a deep sense of musical camaraderie.

Built around themes of travel, legacy, struggle and reflection, the record blends original material with carefully chosen covers, all delivered through the distinctive voices of its four legendary contributors. The chemistry between the artists gives the album a conversational, almost narrative quality, with each singer taking turns in the spotlight.

The title track Highwayman stands as one of country music’s most enduring anthems - a song that moves through time and identity, perfectly suited to the group’s shared persona. Elsewhere, tracks such as Desperados Waiting for a Train, Big River and Deportee (Plane Wreck at Los Gatos) showcase the depth of songwriting and interpretive skill across the album.

Highwayman remains a defining statement of outlaw country — a meeting of four legends whose combined presence elevates every track.

Tracklist

1. Highwayman
2. The Last Cowboy Song
3. Jim, I Wore a Tie Today
4. Big River
5. Committed to Parkview
6. Desperados Waiting for a Train
7. Deportee (Plane Wreck at Los Gatos)
8. Welfare Line
9. Against the Wind
10. The Twentieth Century Is Almost Over