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Highwayman
performed by Jimmy Webb, Glen Campbell, Finn Kalvik, but made popular by The Highwaymen (Willie Nelson, Kris Kristofferson, Waylon Jennings, Johnny Cash)
written by Jimmy Webb
released initially in May 1977 by Jimmy Webb
[Verse 1: Willie Nelson]
I was a highwayman
Along the coach roads I did ride
With sword and pistol by my side
Many a young maid lost her baubles to my trade
Many a soldier shed his lifeblood on my blade
The b*stards hung me in the spring of ’25
But I am still alive
[Verse 2: Kris Kristofferson]
I was a sailor
I was born upon the tide
And with the sea I did abide
I sailed a schooner around the Horn to Mexico
I went aloft and furled the mainsail in a blow
And when the yards broke off they said that I got killed
But I am living still
[Verse 3: Waylon Jennings]
I was a dam builder
Across a river deep and wide
Where steel and water did collide
A place called Boulder, on the wild Colorado
I slipped and fell into the wet concrete below
They buried me in that gray tomb that knows no sound
But I am still around
I’ll always be around
And around, and around, and around
And around, and around, and around…
[Verse 4: Johnny Cash]
I fly a starship
Across the Universe divide
And when I reach the other side
I’ll find a place to rest my spirit if I can
Perhaps I may become a highwayman again
Or I may simply be a single drop of rain
But I will remain
And I’ll be back again
And again, and again, and again
And again, and again…
____________________________
This weird country music songs is one of my all-time favorite songs. I don’t support the message obviously (young maids should not be robbed of their baubles) but the fact that four industry legends formed a supergroup, like they were a professional wrestling stable, was completely awesome to me. [Someone quick, go round up Travis Tritt, Alan Jackson, Clint Black, and Dwight Yoakam.]
This is how I imagine The Highwaymen came together as a group and I will not be persuaded otherwise:
It’s probably not obvious that this song is about one person being reincarnated over and over, though once I tell you that, it should seem obvious. To tell the background more fully, I direct you to the wiki article:
According to Webb, he wrote the song in London while he was finishing up work on his album El Mirage. After a late-night round of “professional drinking” with his friend Harry Nilsson, Webb went to sleep and had “an incredibly vivid dream”:
I had an old brace of pistols in my belt and I was riding, hell-bent for leather, down these country roads, with sweat pouring off of my body. I was terrified because I was being pursued by police, who were on the verge of shooting me. It was very real. I sat up in bed, sweating through my pajamas. Without even thinking about it, I stumbled out of bed to the piano and started playing “Highwayman”. Within a couple of hours, I had the first verse.
Webb included the phrasing in the line “Along the coach roads I did ride” to convey a kind of “antique way of speaking”. Not sure of where the song was leading him, Webb realized that the highwayman character does not die, but becomes reincarnated, and the three subsequent verses evolve from that idea. In the second verse he becomes a sailor, in the third verse a dam builder, and in the fourth verse Webb switches to future tense and the character becomes an astronaut who will someday “fly a starship across the universe divide”.
With a stable of superstars and a great backstory like that, how could this song not go on (eventually) to greatness?
Chart positions
| Chart (1985) | Peak position |
|---|---|
| US Hot Country Songs (Billboard) | 1 |
| Canadian RPM Country Tracks | 1 |
| Canadian RPM Adult Contemporary Tracks | 19 |
Awards
The Highwaymen’s version of the song earned songwriter Jimmy Webb a Grammy Award for 1985‘s “Best Country Song”.
Despite the big names, the supergroup never really proved to be “super” other than their namesake song. Their next biggest hit topped country charts in the #15 spot. The group existed from 1985 until about 1995, which means they were initially stymied by a Nashville that resisted Outlaw Country and then they were next stymied by a youth-led country music renaissance that really began in the late 80s and early 90s. However, the latter event opened the door for the members of the group to eventually have solo success again.
The official music video for this song is also epic. It was filmed in black and white and depicts the individual verses of the song, with the singers appearing in the sky in each scene.
♫Or I may simply be a single drop of rain
But I will remain
And I’ll be back again
And again, and again, and again
And again, and again…♫
Supergroups are subject to super egos sometimes. Other Supergroups; Cream, Traveling Wilbury’s , Prince and Tom Petty et all on While my Guitar Gently Weeps..
Still, always a treat for us fans.
Very true! At least in the case of these guys, I don’t remember there being a lot of public squabbling. I think they were squabbling enough with Nashville and record labels and it kind of brought them together. But I was more of a music listener than a person who followed the behind-the-scenes stuff.
I absolutely love this song. And like you I’m fascinated that the four of them teamed up to make music together.
Yeah, that song is one of my all-time favorites. I didn’t know until I wrote this post that Jimmy Webb wrote the song after a vivid alcohol fueled dream. That knowledge kind of makes me like it even more because it adds to the otherwordly mystique.
Yeah, that actually explains a lot about the lyrics but I think that sort of otherwordly mystique made it really unique for a country song.
Oh for sure. And I think the idea that the song was born out of an unconscious experience kind of makes it spookier even if it does explain it.
I think I’ve read that you’ve studied this, so you probably know more about it than I do, but there definitely used to be more ghost / spooky-stuff room in the genre than there is today. “Ghost Riders in the Sky,” “Long Black Veil,” “The Ride,” etc.
Yeah, I studied Country Music in university. In general, there was a lot more diversity with country music than we see today. And you’re right, there was more spooky related stuff back in the day. Especially before the late 90’s. I feel like once country became more mainstream it changed and the creativity sort of left mostly when it came to more popular songs made for radio.
Yeah. There has definitely been a push to make country music more “cross-genre friendly” over the last 25 years. The pendulum does seem to be swinging back in the other direction now, with Chris Stapleton, Morgan Wallen, etc., but there’s a long way to go.
Oh I absolutely love Chris Stapleton. He’s fantastic. True, it’s slowly changing but I feel like the mainstream songs still just talk about the same five things again and again. It’s frustrating.
The mainstream of country music is just so bland and formulaic. The weird thing is that all the attempts to create cross-over music led to an industry that became less and less relevant overall. I am 100% a conspiracy theorist on this issue, but I think there was an overt attempt to destroy the genre, even if that meant losing money to do it.
Yeah, honestly I’m not into conspiracy theories in general but I wouldn’t be surprised if that one was true. We actually learnt about how that happens to every popular genre. They destroy it for a while so another genre can take its place and make more money. It loses money short-term but makes more money longterm.
I love the song, but it is definitely strange!
Yeah. There used to be a kind of “Southern Gothic” strain in that genre (and literature, plays, etc.) but it has slowly faded away over time. I’m not sure this exactly fits in as “Southern Gothic” though.