When Jimmy Webb wrote “The Highwayman,” the story came after a night of drinking with Harry Nilsson. In the dream, Webb, the singer and songwriter behind Glen Campbell‘s “Wichita Lineman” “Galveston,” and “By the Time I Get to Phoenix,” Art Garfunkel‘s 1973 hit “All I Know,” and more, had become an outlaw, running from the law.
“I was in London, finishing an album, ‘El Mirage,’ with [Beatles producer] George Martin,” said Webb on how the song came to him. “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.”
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Webb continued, “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.”
In 1977, Webb released “The Highwayman” as the opening track from his sixth album El Mirage. A year later, Webb’s longtime collaborator Campbell recorded a version for his 1979 album Highwayman.
4 Stations in Life
Within the song, Webb moved through four incarnations of the soul with incarnations moving that moved through different spaces in time and history, including a sailor, a dam builder, the captain of a starship, and a highwayman.
“I wanted this character in this song to be like a timeless character,” said Webb in 2022. “He has no control over where he ends up, really. He starts out as a highwayman and ends up flying a starship. So in that sense, it’s also a description of the lack of control that any of us have over our destiny, really. So that’s pretty much spelled out in the song, is he’s in the pinball machine of the universe, and he’s banging around from one experience to the next.
The Highwayman
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
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The Sailor
I was a sailor
I was born upon the tide
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 Dam Builder
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 and around and around
The Starship Captain
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
The Highwaymen
The song inspired the name of the outlaw country supergroup The Highwaymen, featuring Johnny Cash, Kris Kristofferson, Willie Nelson, and Waylon Jennings. The band’s version of “The Highwayman” appeared on their 1985 debut Highwayman and went to No. 1 number one on the Billboard Hot Country Songs chart, where it remained for 20 weeks. Webb and The Highwaymen also won a Grammy for Best Country Song in 1986.
Within the song, all four members took on their respective “roles”: Nelson as the highwayman; Kristofferson, the sailor; Jennings, the dam builder; and Cash as the starship captain.
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“This song showed up, where there were four verses and there were four guys, and they could just do their thing,” said Webb. “They split it up themselves. … I think Johnny Cash wanted to be the starship captain. And I think they worked it out pretty well. Willie was the outlaw. Kris Kristofferson was the sailor, which, if you look back on some of his film roles and things, you’ll find that. And Waylon was always this bear. He was a bear. He looked like he could build a dam all by himself.”
Webb added, “Then that pulled Johnny in to be the last guy, which I think they wanted him to be. But the end result was a hit record for them and a kind of shot in the arm for my career. I got right back on, you know, the call list of guys to call. So I was happy.”
In 1996, Webb recorded “The Highwayman” again for his album Ten Easy Pieces, along with a live version on his 2007 album Live and at Large and another version with his sons, The Webb Brothers, for their 2009 album Cottonwood Farm. Webb recorded the song again as a duet in 2010 with Dire Strait‘s Mark Knopfler for his 12th album Just Across the River.
Photo: Rob Verhorst/Redferns
