Review: The Highwaymen’s ‘Highwayman’ remains one of Country’s most important records

There’s often the perception that artists operating in the same genre must be rivals. It’s a narrative that’s been amplified for the media for years but often, it’s simply not the case at all. In 1984, four of the biggest Country music artists in the genre – Kris Kristofferson, Johnny Cash, Waylon Jennings and Willie Nelson – came together as The Highwaymen (a name that took some years to land after the release of their first two albums). The four artists had been admirers of one another for years, with a history between them that surpassed their time in the spotlight up to that point. By the time the legends came together, each was at a different point in their career with Nelson being the biggest star at the time.

The first project from the foursome was 1985’s ‘Highwayman’, which features a mixture of covers and originals across the 10 tracks. The title track was the first single, a cover of Jimmy Webb’s song, and it was a huge hit. The album was produced by Chips Moman and it saw the foursome sharing lead vocals in different combinations. ‘Highwayman’ showcases all four of the artists on lead vocals while three songs on the record – ‘Jim, I Wore a Tie Today’, Cash original ‘Committed to Parkview’ and a cover of Steve Goodman’s ‘The Twentieth Century is Almost Over’ – featured Cash and Nelson on lead vocals.

Running at a fairly lean 34 minutes, ‘Highwayman’ is an important record in the history of Country music. At the time the album was felt to straddle Country and AOR, but listening to it 41 years after its original release, the album is undeniably a classic Country record. The swoonsome ‘The Last Cowboy Song’ captures the camaraderie of the four artists as they sing together, while the punchy ‘Big River’, written by Cash, is an early highlight that showcases how the men’s different voices complement one another. ‘Desperados Waiting for a Train’, originally recorded by Guy Clark who also wrote it, is another highlight on the record and probably one of the group’s best-known songs.

A cover of Woody Guthrie’s ‘Deportee (Plane Wreck at Los Gatos) features Johnny Rodriguez and the protest song is as relevant now as it was back in 1948. Debates around immigration are rife at the moment, particularly in the US, and songs lyrics hit the same buttons all these years on. ‘Welfare Line’ written by British songwriter Paul Kennerley continues the social commentary of its predecessor, tackling the issues that Americans care about. ‘Against the Wind’, originally a hit for Bob Seger, is one of the songs that steps a little outside of Country with a steady beat driving the midtempo melody. It sounds distinctly 80s-influenced, whereas much of the rest of the album doesn’t.

This new reissue from Music on Vinyl is pressed on black vinyl and features a high-quality cardboard sleeve. The original artwork has been faithfully reproduced, and the quality of the sound on the record is outstanding. It’s incredible to thing the album is 41 years old as the sound quality is pristine. I don’t think I’ve ever heard this album sound this good.

‘Highwayman’ is an iconic record and it’s one that is rightly revered in Country music history. Can you imagine four stars of this stature coming together in the modern day? For those fans of traditional Country, ‘Highwayman’ is a treat and if you’re a fan of any of the four men from the group, you’ll find plenty to enjoy. For me, Cash stands out the most thanks to his very distinctive voice but the project succeeded because it played to the strengths of all of the artists.

Track list: Side One – 1. Highwayman 2. The Last Cowboy Song 3. Jim, I Wore a Tie Today 4. Big River 5. Committed to Parkview Side Two – 1. Desperados Waiting For a Train 2. Deportee (Plane Wreck at Los Gatos) 3. Welfare Line 4. Against the Wind 5. The Twentieth Century is Almost Over Record label: Music on Vinyl Release date: 13^th February 2026 Buy ‘Highwayman’ now