"Highwayman" is a song written by American singer-songwriter Jimmy Webb, 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. The dam builder verse alludes to the deaths of over one hundred men during the construction of Hoover Dam near Boulder City, Nevada.
Webb first recorded the song on his album El Mirage, released in May 1977. The following year, Glen Campbell recorded his version, which was released on his 1979 album Highwayman. In 1985, the song became the inspiration for the naming of the supergroup The Highwaymen, which featured Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson.
Their first album, Highwayman, became a number one platinum-selling album, and their version of the song went to number one on the Hot Country Songs Billboard chart in a twenty-week run.
Their version earned Webb a Grammy Award for Best Country Song in 1986. The song has since been recorded by other artists. Webb himself included a different version on his 1996 album Ten Easy Pieces, a live version on his 2007 album Live and at Large, and a duet version with Mark Knopfler on 2010 album Just Across the River.
According to Jimmy Webb, he wrote the song in London while he was finishing up work on his album El Mirage. After a late-night round of "professional drinking" with his friend Harry Nilsson, Webb 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 included the phrasing in the line, "Along the coach roads I did ride" to convey a kind of "antique way of speaking".
Not sure of where the song was leading him, Webb realized that the highwayman character does not die, but becomes reincarnated, and the three subsequent verses evolve from that idea.
In the second verse he becomes a sailor, in the third verse a dam builder, and in the fourth verse Webb switches to future tense and the character becomes an astronaut who will someday "fly a starship across the universe divide".