Jimmy Webb, “Highwayman”


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Some songs immediately find widespread popularity, while some, regardless of their merits, go all but unsung. And then there are a few songs that fail to initially ignite until the right circumstances come along to allow them to thrive. “Highwayman” nearly fell into that unfortunate unsung category, but it turned out to be custom-fit for a project that didn’t even exist when it was written.

Prolific and profound songsmith Jimmy Webb birthed “Highwayman” from a fever dream, as he told Performing Songwriter in an interview in 2015. “I was in London, finishing an album, El Mirage, with George Martin,” he remembered. “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.”

Webb’s solo version, released in 1977, featured Martin’s majestic orchestrations but didn’t make too much of an impact. Neither did Glen Campbell’s take, even though his insistence on recording the song led to him leaving his record label. Campbell eventually brought the song to Johnny Cash, who was in the process of forming a supergroup with Willie Nelson, Kris Kristofferson, and Waylon Jennings. Not only did the quartet realize the song was a perfect fit for their project, containing as it did exactly one verse for each of the participants, but they realized that the themes of indomitability and resilience in the face of turmoil dovetailed nicely with the paths of their respective careers. Thus the Highwaymen were born, releasing “Highwayman” as their lead single in 1985.

Nelson gets the opening lap, his voice full of fire as he recounts the “highwayman” portion of the song, singing with bracing grit and fire about those he victimized: “Many a young maid lost her baubles to my trade/Many a soldier shed his lifeblood on my blade.” The reveal of his fate introduces the twist that drives the song: “The bastards hung me in the spring of twenty-five/But I am still alive.”

As a result, when Kristofferson follows as the sailor, handling Webb’s sea jargon like a grizzled old salt, we’re ready for his refusal to go gently into that good night: “And when the yards broke off they say that I got killed/But I am living still.” Jennings takes the guise of a dam builder whose fate is more gruesome than the rest of his brethren: “I slipped and fell into the wet concrete below/They buried me in that great tomb that knows no sound.” The good news: “But I am still around.”

Webb’s genius choice to set the final verse in the future, where our narrator inhabits a starship, becomes even more momentous once Cash steps behind the microphone. There’s something counterintuitive and shocking about having that booming voice of the earth sail up into the stars, but it all makes sense when the gravity and mystery of Webb’s tale melds with Cash’s delivery in the final lines: “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.”

“Highwayman” soared to #1 in 1985, a happy ending for Webb after the song had languished for so long. Every posse needs a theme song. For a posse as imposing as the one these four music legends formed, only one as inventive and affecting as “Highwayman” could possibly have suited them.

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