Every #1 Country Single of the Eighties: The Highwaymen, “Highwayman”


The Highwaymen

Written by Kix Brooks and Dan Tyler


#1 (1 week)

August 17, 1985

Jimmy Webb wrote “Highwayman” after an incredibly vivid dream, and he was well into the songwriting process when he realized that he was writing about the same man being reincarnated.

That’s easy to lose in translation as the song is transformed into a four part collaboration by legends Willie Nelson, Kris Kristofferson, Waylon Jennings, and Johnny Cash.  The sheer star power alone is awe-inspiring, and because they’re each such distinctive vocalists – yes, even Kris Kristofferson – I am sure there are listeners who never picked up on this being the same highwayman visiting earth again and again.

But it’s all the more powerful when you realize it because it captures something about the human spirit.  There are some people who love to explore new frontiers, and it makes sense that the same drive that would lead you to a life of robbery in the Wild West could also find you captaining an exploratory ship, building a dam in wild Colorado, and even exploring space as an astronaut.

With two of the artists on this record already gone, there’s a poignancy to imagining where there own spirits may have been reborn. “Highwayman” gives us a little taste of immortality, and some solace in the idea that our earthly physical forms may wither and die, but we’ll “always be around and around and around and around.”

An absolute masterpiece that was somehow improved upon a few decades later.

Grade: A  

Every No. 1 Single of the Eighties

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  1. Great song. After I found out it was written by Jimmy Webb, I had to go find out if Glen Campbell ever recorded it; he actually did, and released it on the album of the same name six years before the Highwaymen made it immortal.

    I have to admit it made me feel pretty smart to know what the line ”a place called Boulder on the wild Colorado” was referring to. Some time ago I saw some dude on Reddit say something to the effect that the line was inaccurate because there was no town called Boulder anywhere on the Colorado River. I was like, ”yyyyeah, that wasn’t a town.” Heh.

  2. “. . . I am sure there are listeners who never picked up on this being the same highwayman visiting earth again and again.”

    Wow, I’m embarrassed to admit such listeners included me. This perhaps explains why I’ve always been indifferent to this long-familiar recording, as I’ve never understood it. Through this feature, the song now makes sense to me, and I can finally appreciate its brilliance.

  3. I listened to the Highwomen’s take on this song, and while it quite interesting and well performed I think saying that they improved upon the original is a huge overstatement.

    I must confess that I had forgotten about Glen Campbells version of the song from his 1979 HIGHWAY MAN album. Glen’s version is effective if a bit over-orchestrated. I do not believe that it was released as a single although WHOO and WSUN played it a few times.

    Glen Campbell is undoubtedly a better singer than Cash, Jennings, Nelson or Kristofferson; however, his voice lacks the depth of character (or gravitas, if you will) that made this song such a success for the quartet

  4. The number of classic collaborations Willie Nelson was part of this decade alone is shocking.

    “Pancho and Lefty,” “Seven Spanish Angels,” “To All the Girls I’ve Loved Before”, and now the “Highwaymen.”

    To hear all these icons singing together brought the same excitement to a an 11-year-old boy as when my favourite super heroes teamed up on an episode of the the Super Friends or
    when I had a sleepover with my favourite friends.

    Lyrically and vocally this song is a time-warping and dizzying event. It is a sonic puzzle that is simultaneously in pieces and fully completed.

    Other then Nelson, Kristofferson, Jennings, and Cash were at artistic low points in their careers when this hit.

    A classic through and through.

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