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.
After a late-night round of "professional drinking" with his friend Harry Nilsson, Webb went to sleep and had "an incredibly vivid dream":[1] 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.
[1]Webb included the phrasing in the line "Along the coach roads I did ride" to convey a kind of "antique way of speaking".
[1] 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 1984, Campbell played the song "Highwayman" for Johnny Cash, who was making a quartet album with Willie Nelson, Waylon Jennings, and Kris Kristofferson.
[4] 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.
[citation needed] A black-and-white music video was released, which used actors to re-enact the song's lyrics, including the deaths of the first three characters.
[12] When Brandi Carlile, Natalie Hemby, Maren Morris, and Amanda Shires formed the female supergroup The Highwomen in homage to the Nelson–Jennings–Cash–Kristofferson supergroup, they opened their eponymous 2019 debut album with Shires and Carlile adapting Webb's lyrics (with his blessing and assistance) as a response song reflecting how women throughout history often sacrifice themselves for a greater good, illustrating this with a Honduran immigrant who dies getting her children over the border (sung by Carlile), a healer executed for witchcraft (Shires), a freedom rider (guest vocals from Yola), and a preacher (Hemby).