Country Throwback: How an ‘Incredibly Vivid’ Dream Inspired the Classic Hit ‘Highwayman’

by Suzanne Halliburton
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Think about the words to the “Highwayman.” It’s a classic. The star of the song lives multiple, varied lives. It relies on the supernatural to entice us to follow the tale.

And the song truly came to life when the super grouping of Johnny Cash, Willie Nelson, Kris Kristofferson and Waylon Jennings performed it 35 years ago.

So does it surprise you that a song about the supernatural started out as a dream? That it flickered in the imagination after having consumed one too many adult beverages?

As Jimmy Webb tells it, his dream occurred while he was living in his flat in London way back in the mid-70s. Beatles producer George Martin helped him with his album. And he was up one night drinking with Harry Nilsson, the American singer-songwriter. Nilsson was so close to John Lennon and Ringo Starr, he often was called the “American Beatle.”

Webb told “Performing Songwriter: Nilsson “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.”

Now, that’s how brilliant music is made. It starts out as a morsel of an idea. Maybe it’s inspired by a divine dream. Maybe it’s prompted by a random conversation.

The Song Tells The Story Of A Man Who Lived Four Lives

This song was about a man with four souls. He was a highwayman. The man sailed on a ship. He worked on the Hoover Dam. And he captained a starship. All the incarnations had lyrical details. Webb recorded the song in 1977 for his own album, “El Mirage.”

But the rest of the story about how the song made it to your record or CD player is pretty common. Another singer hears it and loves it. A recording company dawdles. The song ends up with another.

Glen Campbell also recorded “The Highwayman,” adding the song to one of his albums and releasing it in 1979. But it never caught fire the way other hits Webb had written for him. If you’re a fan of the late Campbell, you know the words to those other hits. They included “Galveston,” “Wichita Lineman” and “By the Time I Get to Phoenix.”

Here’s How Four Country Superstars Got the “Highwayman”

Fast forward to the mid-1980s. Country stars Cash, Kristofferson, Jennings and Nelson gathered together to work on Cash’s Christmas TV special in a scenic alpine village in Switzerland. Marty Stuart, a long-time bandmate of Cash’s, suggested they sing the four verses of the “Highwayman.”

The song hit No. 1 on the country charts in 1985. Webb won a Grammy for best country song.

That folks, is a inspirational cautionary tale.

“This is encouragement for young writers with great songs and nothing happens to them,” Webb said. “You can’t sit around and brood about it. You move on and write more. “

Webb worked with country and pop stars. And he’s considered one of the best ever to write a song. He was inducted into the Songwriters Hall of Fame in 1986 and the Nashville Songwriters Hall of Fame in 1990.

And maybe his best work flickered in his mind after a night of “professional drinking.”

Outsider.com