
04/19/2025
🎵The Highwaymen – Highwayman
"Highwayman" is an iconic country ballad performed by the supergroup The Highwaymen, featuring four legends of country music: Johnny Cash, Willie Nelson, Waylon Jennings, and Kris Kristofferson. Released in 1985 as the title track of their debut album Highwayman, the song became a massive hit and is widely considered a classic in American country music.
Written by Jimmy Webb, the song is a poetic journey through reincarnation, with each verse sung by a different member of the group. Each character—a highwayman, a sailor, a dam builder, and a starship pilot—represents a different life and time, bound by the soul’s eternal passage through history. The haunting chorus “I’ll always be around, and around, and around…” echoes the theme of the soul's immortality.
Musically, “Highwayman” combines storytelling with rich, atmospheric country arrangements, each voice adding a unique tone and emotion to their verse. The track showcases the individual strengths of the four artists while uniting them into a powerful, cohesive whole.
“Highwayman” won a Grammy Award and solidified The Highwaymen’s place in music history, not just as a collaboration, but as a brotherhood of outlaw country pioneers. It remains a powerful anthem about identity, legacy, and the enduring spirit of the human soul.