<P> "Highwayman" is a song written by American singer - songwriter Jimmy Webb, about a soul with incarnations in four different places in time and history: as a highwayman, a sailor, a construction worker on the Hoover Dam, and finally as a captain of a starship . The song was influenced by the real - life hanged highwayman Jonathan Wild . The dam builder verse alludes to the deaths of over one hundred men during the construction of Hoover Dam near Boulder City, Nevada . Webb first recorded the song on his album El Mirage, released in May 1977 . The following year, Glen Campbell recorded his version, which was released on his 1979 album Highwayman . In 1985, the song became the inspiration for the naming of the supergroup The Highwaymen, which featured Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson . Their first album, Highwayman, became a number one platinum - selling album, and their version of the song went to number one on the Hot Country Songs Billboard chart in a twenty - week run . Their version earned Webb a Grammy Award for Best Country Song in 1986 . The song has since been recorded by other artists . Webb himself included a different version on his 1996 album Ten Easy Pieces, a live version on his 2007 album Live and at Large, and a duet version with Mark Knopfler on 2010 album Just Across the River . </P> <P> According to Jimmy Webb, he wrote the song in London while he was finishing up work on his album El Mirage, which was produced by George Martin . After a late - night round of "professional drinking" with his friend Harry Nilsson, Webb went to sleep and had "an incredibly vivid dream": </P>

What is the meaning of the highwayman song
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