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 four distinct incarnations: a highwayman, a sailor, a dam builder, and a starship pilot. Each verse delves into the life and demise of these characters, exploring themes of adventure, ambition, and the transcendence of the human spirit.
Webb penned “Highwayman” during a stay in London while completing his album El Mirage. After an intense evening with his friend Harry Nilsson, Webb experienced a vivid dream that inspired the song’s creation. He recounted waking up, still gripped by the dream’s intensity, and composing the first verse almost instinctively. This initial inspiration evolved into a narrative exploring reincarnation and the persistence of the soul across different lifetimes.
The song was first released on Webb’s El Mirage album in May 1977. Glen Campbell, captivated by the song’s narrative, recorded his rendition in 1978, releasing it on his 1979 album Highwayman. Despite Campbell’s enthusiasm, his version did not achieve significant commercial success.
The song gained widespread acclaim when it was recorded by the country supergroup The Highwaymen, consisting of Johnny Cash, Willie Nelson, Waylon Jennings, and Kris Kristofferson. Their rendition, released in 1985, became the title track of their debut album and soared to number one on the Billboard Hot Country Songs chart. This version also earned Jimmy Webb a Grammy Award for Best Country Song in 1986.
The Highwaymen’s live performances of “Highwayman” further solidified the song’s legendary status. A notable rendition was captured during their concert at Nassau Coliseum in Uniondale, New York, on March 14, 1990. This performance was later included in the 2016 release The Highwaymen Live – American Outlaws, a comprehensive collection showcasing the group’s dynamic stage presence and the song’s enduring appeal.
“Highwayman” stands as a testament to the storytelling prowess of Jimmy Webb and the collaborative synergy of The Highwaymen. Its exploration of timeless themes and its journey from a songwriter’s dream to a country music classic underscore its significance in the annals of American music history.