The Highwaymen – Highwayman

Album Info

Artist: The Highwaymen

Title: Highwayman

Year: 1985

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Tracklist

  • 1. Highwayman (3:02)
  • 2. The Last Cowboy Song (3:10)
  • 3. Jim, I Wore a Tie Today (3:21)
  • 4. Big River (2:47)
  • 5. Committed to Parkview (3:20)
  • 6. Desperados Waiting for a Train (4:36)
  • 7. Deportee (Plane Wreck at Los Gatos) (3:45)
  • 8. Welfare Line (2:34)
  • 9. Against the Wind (3:48)
  • 10. The Twentieth Century Is Almost Over (3:35)

Review

Back in 1985, getting these four distinct personalities in a room together must have felt like trying to herd cats, but the result was nothing short of magic. When you listen to "Highwayman," you are hearing the Mount Rushmore of outlaw country—Willie Nelson, Johnny Cash, Waylon Jennings, and Kris Kristofferson—swapping verses on a Jimmy Webb tune about a soul reincarnated through the ages. It is a stirring song that rightfully climbed to No. 1, showcasing a chemistry that felt lived-in and genuine rather than manufactured for sales. Producer Chips Moman kept the arrangements sparse enough to let those weathered voices take center stage, creating a sound that feels as comfortable as a worn-in pair of boots.

The rest of the tracklist is a tour through some of the finest songwriting to ever grace a guitar string, with a heavy focus on drifters and fading frontiers. They breathe new life into Guy Clark's "Desperados Waiting for a Train," blending their harmonies into a somber reflection that peaked at No. 15 on the charts. I particularly enjoy the rowdy energy on "Big River," where Waylon adds his own flavor to Johnny's rockabilly standard, standing in stark contrast to the heavy sorrow found in "Deportee (Plane Wreck at Los Gatos)." From the social commentary of "Welfare Line" to the closing thoughts on "The Twentieth Century Is Almost Over," this gold-certified debut proved that these legends could merge their talents into one unbreakable voice without losing an ounce of their individual character. - Rex