About the song
“Highwayman” is a country song written by Jimmy Webb. It was first recorded by Jennings in 1975 for his album “Dreaming My Dreams.” However, it was the version by Cash, Nelson, Kristofferson, and Jennings that became the most well-known, released in 1985 as a single from their collaborative album “Highwayman.” The song is a ballad about four outlaws who are on the run from the law. The song is full of vivid imagery and Webb’s lyrics are both poetic and suspenseful.
“Highwayman” as a collaborative effort
The song “Highwayman” was a collaborative effort between four of the most iconic figures in American country music: Johnny Cash, Willie Nelson, Kris Kristofferson, and Waylon Jennings. Each of these singers brought their own unique talents to the song. Cash’s deep, resonant voice provides a sense of authority and gravitas. Nelson’s smooth, mellow voice adds a touch of warmth and soul. Kristofferson’s rugged good looks and poetic lyrics add a touch of danger and excitement. And Jennings’ outlaw image and rebellious spirit give the song an edge.
Legacy
“Highwayman” is a classic country song that has been covered by many artists. However, the version by Johnny Cash, Willie Nelson, Kris Kristofferson, and Waylon Jennings is the definitive one. Their performance is a masterclass in country music and a testament to their talent as singers and songwriters. “Highwayman” was also a commercial success, reaching number one on the Billboard Hot Country Singles chart in 1985. The song has been certified platinum by the RIAA and has sold over two million copies.
“Highwayman” in popular culture
“Highwayman” has been used in several films and television shows, including “Thelma and Louise,” “The Big Lebowski,” and “Sons of Anarchy.” The song has also been used in commercials for products such as Dodge trucks and Budweiser beer.
- The song was inspired by Webb’s reading of a poem about a highwayman.
- The song was originally intended to be a duet between Cash and Jennings.
- The song’s music video was directed by Kristofferson.
- The song has been covered by many other artists, including Alan Jackson, Trace Adkins, and Brad Paisley.
- The song was inducted into the Grammy Hall of Fame in 2019.