Pop Song 603 of 1000 'The Highwayman' Jimmy Webb 1977

Pop Song 603 of 1000 'The Highwayman' Jimmy Webb 1977

Live MV by supergroup The Highwaymen Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson. https://www.youtube.com/watch?v=bMdeg-WKt1U&t=3s

Official MV https://www.youtube.com/watch?v=aFkcAH-m9W0
https://www.youtube.com/@CyrusandAurelius/

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":[1]

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.[1]

Webb included the phrasing in the line "Along the coach roads I did ride" to convey a kind of "antique way of speaking".[1] 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.[1] 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"