The Highwayman Edition

On songwriting, immortality, and Waylon

Colin here. Some songs from your youth stay in your brain because they’re catchy (Highway to the Danger Zone from Top Gun!). Others because they’re just spooky. For me, that’s Highwayman, the 1985 ballad sung by Johnny Cash, Willie Nelson, Waylon Jennings, and Kris Kristofferson. I first heard it as a child, and it’s haunted me ever since. I even had it soundtracking my dreams last night.

Why is this interesting?

The song, written by Jimmy Webb, is built on reincarnation. A highway robber, a sailor, a dam builder, and finally, a starship pilot. Each verse ends the same way: the body is gone, but I’ll be back again, and again, and again.

As a child, there was a lot of death packed into one song. The outlaw hanged. The dam builder who sings “I slipped and fell onto the wet concrete below.” Yet in the song they live on. Then the voice changes. It is Nelson, then Jennings, then Cash. Was it the same soul, or just another singer? It did not quite make sense. But the images were so vivid: gallows, storm, dam, spaceship, that I could not shake them.

Now that I am older, I see that part of the magic is who was singing it. By the mid-1980s, Nelson, Jennings, Cash, and Kristofferson were already larger than life. Each had carved out a legend in the outlaw era of country (future WITI incoming!), rebelling against Nashville polish with grit, independence, and mythmaking of their own. To bring them together in one song was almost absurd: four towering figures taking turns inhabiting the same restless soul.

And then there is Webb himself. He was not a country insider but a songwriter with a reputation for ambition. This is the man who turned a lonely telephone lineman into high art (Wichita Lineman), who could make a breakup feel like a sweeping epic (By the Time I Get to Phoenix). He wrote in big, mythic brushstrokes. With Highwayman, he pushed further, from gallows to sea to concrete to space. A meditation on reincarnation that somehow made sense as a country song.

He even wrote a fifth verse about returning as a raindrop or a seed in a wheat field, but the Highwaymen cut it, ending instead with Cash’s cosmic pilot.

Even the album cover leans into that uncanny timelessness. Four famous faces loom like ghosts over the desert. (CJN)