Lyric discussion by Outpour 

This song is actually group song by Waylon Jennings, Willie Nelson, Johnny Cash, and Kris Kristofferson. They got together in 1985 and formed the “Super-group” known as the Highwaymen, which recorded three albums before Waylon and Johnny passed away.

This was the first track on their first album. Each stanza (each persona) was sung by a different man. What does it mean? I think it represents the continuity of man. Our resilience to death, to eradication, to continued existence. But what does the last part of the last stanza mean?

"Perhaps I may become a highwayman again Or I may simply be a single drop of rain "

Perhaps we shouldn't forget what we once were? In the midst of life don't forget simple things that can bring relief.

No, actually the song was written in 1977 by Jimmy Webb and was included in his 'El Mirage' album. Apparently 'The HighwayMEN' liked the song enough to base the name of their new (in 1985) group on it.

Always give credit where REAL credit is due, even if it requires a minute or so to check your facts. *¬◊

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