I was first inspired to write the original version of this post after seeing the news that Kris Kristofferson died back in 2024. Now, I was never really a particularly big fan of his specifically, or even Country Music in general – but I was at least enough of a fan of his music, movies (Blade in particular), and at least one video game, that the news hit me harder than the typical celebrity death does.
Though I was also pretty shook by the deaths of Randy Savage and Tom Petty.
In light of the subject matter of the song, I remember doing this write-up being pretty poignant.
In a way, The Highwaymen are the Traveling Wilburys of musical supergroups. Bringing together country music icons Johnny Cash, Waylon Jennings, Willie Nelson, and, of course, Kris Kristofferson in the mid-eighties recorded three albums, two of which went platinum.
The album Highwayman topped the US Country music charts, and its self-titled single was the number-one country single in both Canada and the US.
It’s pretty deep for a song that’s barely three minutes long.
Each of the group’s four members sings one verse, telling the story of a reincarnating soul that meets an untimely end in each of its lifetimes — Willie Nelson is the highwayman of the title (caught and hanged), Kris Kristofferson is a sailor (fell off the mast), and Waylon Jennings is a worker building the Hoover Dam (fell into the dam’s still-wet concrete; there are about 100 recorded deaths during construction but none of them involved drowning in wet concrete, which would create major issues with the dam’s structural integrity).
In the last verse, Johnny Cash is one of that soul’s future incarnations, singing about exploring the cosmos one day, and the eternal recurrence of death and rebirth:
I[‘ll] fly a starship
Lyrics via Genius.
Across the Universe divide
And when I reach the other side
I’ll find a place to rest my spirit if I can
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.
Again, it’s not an especially long or complex song, but there’s a lot of poignant philosophising and thematic statements packed into it.
Take a listen to it here:
And the full playlist is here.
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