The Mount Rushmore of Outlaw Country: The Story Behind “Highwayman” by The Highwaymen

Johnny Cash, Willie Nelson, Waylon Jennings, and Kris Kristofferson could be considered the Mount Rushmore of the Outlaw Country movement. All four admired each other’s work. Cash shared an apartment with Jennings between marriages in the late ’60s, and Jennings paired with Nelson on many projects through the years. Cash, Jennings, and Nelson all recorded songs written by Kristofferson. All four had acquired superstar status, but only Nelson continued the high level of success into the ’80s. The other three’s careers had all experienced lulls. Meanwhile, contemporary country radio largely ignored these legendary figures when they joined forces to record an album. Let’s look at the story behind “Highwayman” by The Highwaymen.

How They Came Together

The band was unnamed when they first came together. Their first two albums were released under “Nelson, Jennings, Cash, Kristofferson.”

Jennings wrote in his 1996 memoir Waylon, “John had brought our four personalities together initially, in Montreux, Switzerland, in 1984. Every year, he had a television Christmas special, and that holiday season, he wanted us all to come over. … We started trading songs in the hotel after we worked on the special, and someone said, like they always do, we ought to cut the album. … Usually, everyone goes their separate ways after that, but the idea took hold.”

I was a highwayman
Along the coach roads, I did ride
With sword and pistol by my side
Many a young maid lost her baubles to my trade
Many a soldier shed his lifeblood on my blade
The bastards hung me in the spring of ’25
But I am still alive

How the Song Got to Them

In 2017, singer/songwriter Marty Stuart shared the story during a promotional interview for his album Way Out West, “So, we left Montreux going, ‘Willie and John are gonna record a new record as soon as we get home.’ So they hastily put together some songs and sessions. After two days, nothing had really mattered. It just didn’t have any magic. Their voices were so polar opposite.

“So, a buddy of mine named Carl Jackson, who I grew up with, played with Glen Campbell. He kept telling me about a song called ‘The Highwayman’ that Jimmy Webb had done—had written that Glen Campbell had recorded. My cousin Marty Gamblin ran Glen Campbell’s publishing company. So during a break at one of the sessions, I called Marty and said, ‘Do you have a song there called ‘The Highwayman?’ and he said, ‘Yeah.’ I said, ‘Make me a copy.’

“I went and picked it up, and I walked in the control room. I said, ‘Chips and John, I need to see you. Listen to this.’ Four verses. Four guys. No harmony required. And John said, ‘Play it again.’ And he said, ‘I want that verse about the starship. And it went on to become a hit, and that was his first glimmer of hope in a lot of years. And it gave me, all of a sudden, a presence around the building. ‘That’s the kid that found that song for those guys.’”

I was a sailor
I was born upon the tide
And with the sea, I did abide
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
But I am living still

The Song Came from a Dream

Songwriter Jimmy Webb shared the story of the song’s creation in 2012 with Performing Songwriter magazine, “I was in London, finishing an album, El Mirage, with [producer] George Martin. My friend Harry Nilsson was there, and we were doing some professional drinking. He left my apartment one night, and I went to sleep and had an incredibly vivid dream. I had an old brace of pistols in my belt, and I was riding, hell-bent for leather, down these country roads with sweat pouring off of my body. I was terrified because I was being pursued by police, who were on the verge of shooting me. It was very real. I sat up in bed, sweating through my pajamas. Without even thinking about it, I stumbled out of bed to the piano and started playing ‘Highwayman.’ Within a couple of hours, I had the first verse.”

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 great tomb that knows no sound
But I am still around
I’ll always be around, and around, and around, and around, and around

Reincarnation

Webb continued, “I didn’t know where the song was going. Then I realized that this guy doesn’t really die in the first verse. He’s reincarnated. I thought, ‘Where does this soul go?’ The verses started to evolve. He becomes a sailor, then a dambuilder. Then, the best idea for me was switching the tense into the future and say, I’ll fly a starship across the Universe divide until I reach the other side. After I recorded it, the song languished for years. This is encouragement for young writers with great songs, and nothing happens to them. You can’t sit around and brood about it. You move on and write more. Eventually, Glen Campbell did ‘The Highwayman.’ He actually left Capitol Records because they wouldn’t put the song out. So the song not only didn’t get recorded—the only guy who recorded it couldn’t even get his label to release it.

“There were four verses to ‘’The Highwayman.’ Talk about predestination. I don’t know how they decided who would take which verse, but having Johnny last was like having God singing your song.”

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
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, and again, and again

Merle Haggard

When asked about being offered the chance to become the fifth member of The Highwaymen, Merle Haggard told Country 92-5 radio in Hartford, Connecticut, “I turned it down because I said, ‘Hell, it will cut the money down so low so the four of you guys won’t even want to do it.’ But they did offer me a part.”

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