The Highwayman Song
Country music legend Johnny Cash, right, performs with the Highwaymen in October 1985 with Willie Nelson, left, Kris Kristofferson, second from left, and Waylon Jennings, second from right, in Nashville, Tenn. Cash, known as "The Man in Black" and famous for songs like "I Walk the Line," "Ring of Fire" and "A Boy Named Sue," died Friday, Sept. 12, 2003 from complications from diabetes in Nashville. (AP Photo/Mark Humphrey)

Story Behind the Song: The Highwaymen's Signature Hit, 'Highwayman'

Like the starship captain in its last verse, songwriter Jimmy Webb's "The Highwayman" soared beyond the stratosphere in 1985 when it became associated with The Highwaymen. The supergroup of Kris Kristofferson, Johnny Cash, Waylon Jennings and Willie Nelson took turns portraying the different lives of a reincarnated soul on what became a No. 1 hit and Grammy award winner (Best Country Song, 1986).

Before that, "The Highwayman" (sometimes titled "Highwayman") got a few chances to woo the record-buying public, but not even a star as bright as Glen Campbell interfered with the Highwaymen's seemingly predestined role as the right act to share Webb's mystic tale with the masses.

For Webb, it all began with a dream about the Old West.

"I was in London, finishing an album, El Mirage, with [Beatles producer] George Martin," Webb told Performing Songwriter. "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."

After considering what happened to the restless soul of his highwayman, Webb wrote verses about a sailor, a worker on the Hoover Dam and a space traveler. You could say Webb's lead character goes from Roy Rogers (had he robbed stage coaches) to Buck Rogers in just a few lines.

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"The Highwayman" debuted in 1977 on El Mirage, a strong statement of Webb's singer-songwriter greatness but hardly a launching pad for hit Billboard singles. Two years later, the song became the title track of a Campbell album. Although Campbell still played a hot hand for Capitol Records, he failed to duplicate past success found with Webb-penned songs ("By the Time I Get to Phoenix," "Galveston," "Wichita Lineman").

"After I recorded it, the song languished for years," Webb told Performing Songwriter. "This is encouragement for young writers with great songs and nothing happens to them. You can't sit around and brood about it. You move on and write more. Eventually, Glen Campbell did 'The Highwayman.' He actually left Capitol Records, because they wouldn't put the song out. So the song not only didn't get recorded—the only guy who recorded it couldn't even get his label to release it."

For the Highwaymen's debut album, the foursome cut memorable versions of Guy Clark's "Desperados Waiting for a Train" and Bob Seger's "Against the Wind." Yet it's the song that provided the country supergroup with its name that stands out as Kristofferson, Cash, Jennings, Nelson and producer Chips Moman's greatest shared contribution to country music.

Shortly after the Highwaymen concept took shape while all four members worked together on a TV special in Switzerland, longtime Cash bandmate and future Hall of Fame inductee Marty Stuart suggested Webb's song as an ideal four-part duet.

More recently, the Highwomen paid homage to their supergroup predecessors with "Highwoman," a socio-political re-write that finds a similar rebellious spirit in Freedom Riders and other women throughout history.

"The Highwayman" Lyrics

I was a highwayman
Along the coach roads I did ride
With sword and pistol by my side
Many a young maid lost her baubles to my trade
Many a soldier shed his lifeblood on my blade
The bastards 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
I'll always be 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

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