Boomer Anthems: Highwayman

According to Webb, he wrote the song in London while he was finishing up work on his album El Mirage. After a late-night round of “professional drinking” with his friend Harry Nilsson, Webb 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.

Webb included the phrasing in the line, “Along the coach roads I did ride” to convey a kind of “antique way of speaking”. Not sure of where the song was leading him, Webb realized that the highwayman character does not die, but becomes reincarnated, and the three subsequent verses evolve from that idea. In the second verse, he becomes a sailor, in the third verse a dam builder, and in the fourth verse Webb switches to future tense and the character becomes an astronaut who will someday “fly a starship across the universe divide”.–   Via La Wik 

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 twenty-five
But I am still alive

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 and furled the mainsail in a blow
And when the yards broke off they said that I got killed
But I am living still

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

I 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