For the Sake of the Song: Waylon Jennings, Willie Nelson, Johnny Cash, Kris Kristofferson “Highwayman”

Cover art for "Highwayman"

In the mid-1980s, Willie Nelson, Waylon Jennings, Kris Kristofferson and Johnny Cash formed a supergroup, eventually known as The Highwaymen, recording and performing intermittently over a period of 10 years, during which time they released three albums. Actually, the name The Highwaymen was only officially applied to the group for their third LP, 1995’s “The Road Goes on Forever“; prior to this point, the releases were credited to Waylon Jennings, Willie Nelson, Johnny Cash, Kris Kristofferson.

The story as to how the supergroup came together is interesting and it seems that Marty Stuart may be to thank for the four Country Music Hall of Famers getting together. All four singers were together in Switzerland for a Christmas television programme and it was suggested that they should come together for a project. Separately, Chips Moman, Nelson’s producer, was encouraging Nelson to do some recording with Cash, but when Nelson and Cash sang, their voices didn’t harmonise well together. At this stage Stuart, a member of Cash’s band, introduced the song ‘Highwayman‘ and suggested it would work well with four different singers each singing a verse, with no harmony required.

Highwayman‘ was the band’s debut single, reaching number 1 in the US country chart. It was written and first recorded by Jimmy Webb, appearing on his 1977 album “El Mirage” and in 1979, it appeared on Glen Campbell’s “Highwayman” LP. The Jennings, Nelson, Cash and Kristofferson version won Webb a Grammy Award in 1985 for ‘Best Country Song’.

The song features four verses, each representing a different character and each sung by a different member of the band: Nelson is first up, singing about his life as an outlaw, holding up travellers and robbing them at gunpoint “I was a highwayman, along the coach roads I did ride, With sword and pistol by my side” eventually he was caught and hung.

Next up is Kristofferson “I sailed a schooner ’round the horn to Mexico, I went aloft to furl the mainsail in a blow, And when the yards broke off, they said that I got killed“.

Then it’s Jennings’ turn to regale the tale of being a construction worker at the site of the Hoover Dam, “I was a dam builder across the river deep and wide, Where steel and water did collide, A place called Boulder on the wild Colorado, I slipped and fell into the wet concrete below, They buried me in that grey tomb that knows no sound.

Finally we come to Cash, who pilots a spaceship, “I’ll fly a starship across the universe divide, And when I reach the other side, I’ll find a place to rest my spirit if I can.

There is a definite theme, that of reincarnation; each verse’s lyric include a reference, be it Nelson’s “But I am still alive“, Jennings’ “But I am living still“, Kristofferson’s “But I am still around, I’ll always be around and around and around” or most definitively Cash’s “Perhaps I may become a highwayman again, Or I may simply be a single drop of rain, But I will remain, And I’ll be back again and again and again.

Fast forward to 2019, when another supergroup released a version of the song; however this time the artists involved were all female. The Highwomen is a group formed of Brandi Carlile, Maren Morris, Amanda Shires and Natalie Hemby, along with guest artists. Shires and Carlile rewrote the lyrics of the ‘Highwayman‘ song and contacted Webb, asking for his blessing, which he duly gave. Morris does not sing a solo verse here, the third verse being delivered by guest vocalist, Yola.

In The Highwomen’s song, the characters have been changed to women; a mother, a healer, a freedom rider and a preacher, portraying some of women’s struggles throughout history, and the sacrifices they have made for their causes. All of the characters experienced adversity; the mother and her children became refugees, fleeing from conflict; the healer being hung at the Salem gallows hill, after being accused of practising witchcraft; the freedom rider perished on a Greyhound bus bound for Mississippi; and the preacher was teaching at a time when society deemed this was an inappropriate role for a woman and she was hunted down. This version of the song boasts an additional verse, which is sung by all members of the group; it’s an extremely powerful verse, with the lyrics being “We are The Highwomen, Singing stories still untold, We carry the sons you can only hold, We are the daughters of the silent generations, You sent our hearts to die alone in foreign nations, It may return to us as tiny drops of rain, But we will still remain.

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I don’t think the song is about reincarnation but that a persons memory stays around and around and around.


This is a good song for today’s time but never the highwaymen.

Last edited 1 month ago by Karen

I don’t care what anybody says you’re a great group of guys just playing your hearts out


The best part of the highway man, is Waylon part, you don’t hear his guitar in the entire song, until his part, and let loose, and a small part during cash’s, awesome

Ryan Fox

That’s a really good rewrite. Although the original is a classic they’ve managed to find a new authentic truth that really makes you think, reflect and feel. Thanks for bringing this to me Peter 😊


There doesn’t need to be a remake. Willie, Cash, Waylon, & Kristoferson’s version is the definitive version.
Not everything needs to be copied.
Do something original. The Highway Men are legendary.