Introduction
“Highwayman” is a seminal track that not only showcases the collaborative genius of four country music legends—Johnny Cash, Willie Nelson, Waylon Jennings, and Kris Kristofferson—but also tells a compelling narrative of reincarnation across different eras. Written by Jimmy Webb in 1977, the song’s journey to prominence is as captivating as its lyrics.
The inception of “Highwayman” occurred during a vivid dream Webb experienced after a night of “professional drinking” with his friend Harry Nilsson in London. In this dream, Webb found himself as a highwayman fleeing from the authorities, which inspired the song’s first verse. Recognizing the potential of a soul’s journey through time, he expanded the narrative to include subsequent incarnations as a sailor, a dam builder, and finally, a starship pilot, each meeting a tragic end yet persisting into the next life.
Initially, Webb recorded “Highwayman” for his 1977 album El Mirage. Glen Campbell, intrigued by the song’s depth, covered it in 1979 and even titled his album after it. Despite these efforts, the song didn’t achieve significant commercial success until it reached the hands of the four country icons.
The formation of the supergroup that would become known as The Highwaymen was serendipitous. In 1984, Cash, Nelson, Jennings, and Kristofferson were in Switzerland for a television special. During this time, Marty Stuart suggested “Highwayman” as a perfect fit for the quartet, given its four distinct verses. Embracing the idea, they recorded the song with each artist delivering a verse: Nelson as the highwayman, Kristofferson as the sailor, Jennings as the dam builder, and Cash as the starship pilot. This collaboration not only led to the song’s resurgence but also inspired the group’s name and the title of their debut album, Highwayman.
Released in 1985, The Highwaymen’s rendition of “Highwayman” soared to No. 1 on Billboard’s Hot Country Songs chart, marking a pinnacle in each artist’s career. The song’s success was further cemented when it earned Jimmy Webb a Grammy Award for Best Country Song in 1986. The accompanying black-and-white music video featured dramatic reenactments of each character’s story, concluding with the quartet’s faces etched into a Mount Rushmore-like monument, symbolizing their monumental impact on country music.
“Highwayman” stands as a testament to the storytelling prowess of country music and the unique synergy achieved when four legendary artists unite. Its exploration of themes like mortality, resilience, and transcendence continues to resonate, solidifying its place as a timeless classic in the annals of music history.