Introduction
“Highwayman” is a narrative song penned by American singer-songwriter Jimmy Webb, first appearing on his 1977 album El Mirage. The composition weaves the tale of a soul’s journey through four distinct incarnations: a highwayman, a sailor, a dam builder, and an astronaut. Each verse delves into the life and demise of these characters, culminating in the spirit’s continual rebirth, symbolizing resilience and the enduring human spirit.
Glen Campbell recognized the song’s profound narrative and recorded it for his 1979 album, also titled Highwayman. His rendition laid the groundwork for the song’s subsequent prominence.
The song’s most renowned version emerged in 1985 when country music luminaries Willie Nelson, Waylon Jennings, Johnny Cash, and Kris Kristofferson—collectively known as The Highwaymen—came together to record it. Each artist embodied a verse, bringing unique gravitas to their respective characters: Nelson as the highwayman, Kristofferson as the sailor, Jennings as the dam builder, and Cash as the astronaut. This collaboration not only propelled the song to the top of the Billboard Hot Country Songs chart but also solidified The Highwaymen’s legacy as a supergroup.
In a heartfelt homage to their legendary grandfathers, Whey Jennings and Thomas Gabriel—grandsons of Waylon Jennings and Johnny Cash, respectively—joined forces to perform “Highwayman.” Their rendition serves as a bridge connecting past and present, honoring the rich legacy of their forebears while introducing the timeless narrative to newer audiences. Their performance has been lauded for its authenticity and reverence, resonating deeply with fans of traditional country music.
The enduring appeal of “Highwayman” lies in its exploration of themes such as adventure, sacrifice, and the cyclical nature of existence. The song’s ability to transcend time is further evidenced by its reinterpretation by The Highwomen—a female supergroup comprising Brandi Carlile, Natalie Hemby, Maren Morris, and Amanda Shires—in 2019. Their version, “Highwomen,” reimagines the narrative from the perspectives of women throughout history, underscoring the song’s versatility and profound impact.
Through its rich storytelling and evocative melodies, “Highwayman” continues to captivate audiences, serving as a testament to the enduring power of music to convey universal human experiences across generations.