Introduction
“Highwayman” is a seminal song that not only showcases the storytelling prowess of its writer, Jimmy Webb, but also stands as a testament to the collaborative spirit of country music legends. First appearing on Webb’s 1977 album “El Mirage,” the song narrates the journey of a soul through various incarnations—a highwayman, a sailor, a dam builder, and a starship pilot—each meeting their end only to be reborn, symbolizing resilience and the enduring human spirit.
The song gained significant attention when Glen Campbell recorded it for his 1979 album, also titled “Highwayman.” It was Campbell who introduced the song to Johnny Cash, planting the seed for what would become a historic collaboration.
In December 1984, during a television special in Switzerland, Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson—each a towering figure in the outlaw country movement—contemplated a joint project. Marty Stuart, a member of Cash’s band, reminded them of “Highwayman,” suggesting that its four distinct narratives could be perfectly divided among the quartet.
Embracing the concept, the four artists recorded “Highwayman” at Nashville’s Moman Studios, with each taking a verse: Nelson as the highwayman, Kristofferson as the sailor, Jennings as the dam builder, and Cash as the starship pilot. This rendition not only topped the Billboard Hot Country Songs chart but also earned Webb a Grammy Award for Best Country Song in 1986.
The success of the single led to the formation of the supergroup The Highwaymen, named after the song. They released their debut album, also titled “Highwayman,” in 1985, followed by two more albums over the next decade. Their collaboration brought renewed attention to the outlaw country genre and solidified their legacy as pioneers who challenged the conventions of Nashville’s mainstream country scene.
The song’s influence extended beyond its initial release. In 2019, a new supergroup named The Highwomen—comprising Brandi Carlile, Maren Morris, Amanda Shires, and Natalie Hemby—reimagined “Highwayman” to reflect women’s perspectives throughout history. With Webb’s blessing, they crafted verses about a healer accused of witchcraft, a freedom rider, and other female figures, highlighting the struggles and resilience of women across time.
“Highwayman” remains a poignant exploration of life’s cyclical nature and the enduring spirit of humanity, resonating across generations and inspiring artists to reinterpret its themes in new contexts.