“Highwayman” is a song that American singer-songwriter Jimmy Webb created. The lyrics share the story of incarnations. In four different places in time and history, the soul reincarnates as a highwayman, a sailor, a construction worker on the Hoover Dam, and as a captain of a starship. Webb’s inspiration to the track came from a man named Jonathan Wild, the real-life hanged highwayman.
The first artist that Webb talked to was Waylon Jennings. Jimmy brought the song to him. However, when Jennings heard the Campbell version, he said that he just could not see it then. Sometime in 1984, Glen Campbell played the song “Highwayman” for Johnny Cash. At that time, Cash was making a quartet album with Willie Nelson, Waylon Jennings, and Kris Kristofferson. The four were all together in Switzerland doing a television special and decided that they should do a project together.
How “Highwayman” Came to Life
While the four were recording their first album, Marty Stuart played the song for Cash again. He said that it would be perfect for them—four verses, four souls, and four of them. Campbell played the song all over again, but this time to the four of them. From there, the quartet had the name for their new supergroup—The Highwaymen. Eventually, the four signers used Highwayman as the name of their first album and single. The four thought it was a perfect name for them because they were always on the road. In addition, it matched with all four of them having the image of being outlaws in country music.
The Highwaymen’s version of the song had different performers for each of the four verses. The first verse was Nelson’s as the highwayman. Kristofferson as the sailor sang the second verse. The third was Jennings’ part as the dam builder. Finally, Cash took the part of the starship captain. In an interview with Webb, he later observed that he had no idea how the four decided which verse one would take. He added that having Johnny Cash last was like having God singing one’s song. Rosanne Cash shared that her father did not realize the song was about reincarnation until she explained it to him.
The Music Video
In the black-and-white music video released, the director used actors reenacting the song’s lyrics.
They included the deaths of the first three characters. Up in the sky, we can see each of the performers singing a few lines for a short time as their segment of the song concludes.
highwayman, The Highwaymen