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The Highwayman

  • Writer: Doreen Flewell Klatt
    Doreen Flewell Klatt
  • Jan 13
  • 3 min read

I enjoy all types of music. When a song captures my attention, I like to research the story behind the song. The song “the Highwayman” is an intriguing example of somebody’s unique imagination. It is a song about reincarnation written by American singer-songwriter Jimmy Webb. According to Wikipedia he got the influence to write the lyrics after dreaming that he was a Highwayman on the run from the law. (If you read his account, it was more like a nightmare rather than a dream as he reported being so scared he woke up in a full sweat). That very night, he got up and wrote the “Highwayman”. The song is about a soul living on after death. The verses were four different stories of places in time and history; as a highwayman, a sailor, a dam builder on the Hoover Dam, and finally as a captain of a starship. Through its stirring lyrics and shifting narrative voices, Webb crafts a story that spans centuries, imagining the persistence and endurance of the soul through various lifetimes and identities. (if you’re not an adventurer, it will be an exhausting journey!)

Starting with the line “I was a highwayman” establishes romance and danger according to Wikipedia. In the context of early 18th-century England, highwaymen were both feared and romanticized, when in fact, they were simply thieves and robbers! It’s a mystery why the lawless outlaws in history were/are romanticized, but the fact remains.

The song, “The Highwayman” was so great that four country legends: Johnny Cash, Willie Nelson, Kris Kristopherson and Waylon Jennings, who were labelled the “Outlaw Country singers” of all time, named their super group after it. “The Highwaymen”. They recorded the song and it was a number one major commercial and critical hit on the “Billboard Hot Country Songs chart” in 1985. Google defines it this way: “That meant it was both widely popular with the general public and highly respected by industry professionals and critics”.

Each of these legends sang a verse; each time the lyrics say they were killed, the next line is about them living on. Additionally, at the end of Johnny Cash’s verse, he sings that “he may become a single drop of rain, and I’ll be back again and again…”

In the YouTube video of the Highwayman, the elements of the background music and action scenes add to the grandeur of the story. It transport sits audience across time and space through powerful imagery and sound. The addition of lightning and thunder adds excitement and anticipation. The coaches that travelled the roads stretching into the distance and the pounding of hooves, the tumultuous and angry sea, the towering Hoover Dam, and the boundless universe as a starship glide through the cosmos. The combination of this sight and sound makes viewers feel as though they are part of a grand journey, experiencing the drama, adventure, and emotion firsthand. The Highwayman character riding a spirited horse and demanding purses, jewellery and coin from travellers and in another scene, winning the fight against soldiers who were patrolling the area. The sailor, having lived his entire life on the sea, braving every challenge within and without tumultuous waters, is killed. His badge of honour was his strength and survival to the end. The demise of the dam builder falling and “buried in the tomb that knows no sound” suggests an atmosphere of eternal silence and isolation. His fate is sealed within the immense structure he helped build. The dam becomes his final resting place. Finally, the captain of the starship speaks of a freedom “flying across the universe divide” The “Universe divide” suggests a boundary between known and unknown, life and afterlife. He says “I’ll find a place to rest my spirit if I can…or I might become a Highwayman again…”

The “Highwayman” song explores the idea of reincarnation. You may have your own beliefs. I am firm in my Christian belief in the eternal nature of life through ChristJesus andI do not believe in reincarnation. Nevertheless, that’s the true story behind this interesting song andI really enjoyed researching this project. (References: Google, Wikipedia, You-Tube).

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