Introduction
“Highwayman” is a song written by American singer-songwriter Jimmy Webb, first recorded in 1977. The song narrates the journey of a soul through various incarnations: a highwayman, a sailor, a dam builder, and a starship pilot. Each verse explores the life and death of these characters, reflecting on themes of adventure, mortality, and rebirth.
Webb’s inspiration for “Highwayman” came from a vivid dream he experienced after a night of “professional drinking” with his friend Harry Nilsson in London. In this dream, Webb found himself as an outlaw being pursued, which led him to write the first verse about the highwayman. The subsequent verses evolved to depict different lives, culminating in a futuristic starship pilot, symbolizing the soul’s eternal journey.
Initially, “Highwayman” was recorded by Webb for his 1977 album “El Mirage.” Glen Campbell later covered the song in 1979 on his album “Highwayman.” However, it wasn’t until 1985 that the song gained significant acclaim when it was recorded by the country supergroup The Highwaymen, consisting of Johnny Cash, Willie Nelson, Waylon Jennings, and Kris Kristofferson. Each member took a verse, bringing their unique vocal styles to the narrative. Their rendition became a number one hit on the Billboard Hot Country Songs chart and earned Webb a Grammy Award for Best Country Song in 1986.
The Highwaymen’s version of “Highwayman” not only showcased the talents of its members but also solidified the song’s place in country music history. Its exploration of timeless themes and the collaboration of legendary artists have made it a classic, resonating with audiences across generations.