The Highwayman (Music Video and Lyrics)

The Highwayman song became the inspiration for the supergroup the Highwaymen,...watch the music video and see the lyrics and song meaning here.

In 1985, The Highwayman song became the inspiration for the naming of the supergroup the Highwaymen, which featured Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson.  It was a rare time in country music history that so much talent amassed for a single song.  This song became the only song to reach #1 on the country chart by The Highwaymen supergroup reaching the top of the chart starting September 28, 2010.

The Highwaymen Band (Willie Nelson, Waylon Jennings, Johnny Cash, and Kris Kristofferson)

photo: Artist Social Media
Starting August 17, 1985, The Highwaymen’s version of the song went to #1 on the Hot Country Songs Billboard chart for a 20-week run.   The original Highwayman song was written and recorded by American singer-songwriter Jimmy Webb.  The Highwaymen version of the song earned Jimmy Webb a Grammy Award for Best Country Song in 1986. Columbia released the “Highwayman” album on May 2, 1985.

In the Highwaymen’s version of the song, each of the four verses was sung by a different performer: first Nelson as the highwayman, then Kristofferson as the sailor, then Jennings as the dam builder, and finally Cash as the starship captain.  The music video became the most popular of They Highwayman’s career with over 51 million views as of August of 2023.  Watch the music video for the song and see the lyrics and song details below.

The Highwayman Music Video

The “Highwayman” song is about a soul with incarnations in four different places in time and history: as a highwayman, a sailor, a construction worker on the Hoover Dam, and finally as a captain of a starship. The song was influenced by the real-life hanged highwayman Jonathan Wild. Webb’s version of the song was first released on the album El Mirage in May 1977.  Country star Glen Campbell also recorded a version of this song in 1978.

Check out the written lyrics below.

The Highwayman Lyrics

I was a highwayman
Along the coach roads I did ride
With sword and pistol by my side
Many a young girl lost her baubles to my trade
Many a soldier shed his lifeblood on my blade
They finally 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
Yes, I’ll always be around and 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 and again and again

Remember to “share: The Highwayman song with other Country Music fans!

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