We Are The Highwaymen: A County Supergroup

Who are the Highwaymen?

An American county supergroup made up of the four biggest stars of the outlaw country subgenre, Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson. Their career together may have only lasted 10 years, 1985-1995, but the four men worked together before and after as well as reuniting on several different occasions. They released three albums two on Columbia, Highwayman (1985) and Highwayman 2 (1990), and one with Liberty Records, The Road Goes On Forever (1995).

Their influence can be felt throughout the music industry even inspiring an all-female country supergroup named The Highwaywomen. Brandi Carlile, Natalie Hemby, Maren Morris, and Amanda Shires perform a re-written version of the groups’ hit song Highwayman, which you can listen to below.

The Man In Black: Johnny Cash

Johnny Cash

The Man In Black feels like the anchor of the group, with his rich baritone voice and calming influence, Johnny Cash is probably the most recognizable of the four.

Born J. R. Cash on 26th February 1932, in Kingsland, Arkansas, he would go on to be one of the biggest and most well know country stars of the last century. His music and style has inspired a whole generation of artist and musicians amongst people from every walk of life. A man of the people, a rebel, and a god-fearing man, he was a man of many contradictions, but he was always himself.

On stage, he was a rebellious free thinking unapologetic man with a calm bass-baritone voice while his demeanor was that of a somber and humble man. He performed free prison concerts, advocated for Native American rights, and wore an all-black stage outfit earning him the nickname of The Man In Black. He passed away on 12th September 2003.

The Prolific Songwriter: Kris Kristofferson

Kris Kristofferson

A songwriter to his core there are many songs you’ve probably heard that you didn’t know were written by the almighty powerhouse that is Kris Kristofferson.

Kristofferson was born on 22nd June 1936 in Brownsville, Texas as Kristoffer Kristofferson. What a name from the man whose grandparents emigrated from Sweden. He retired in 2021 and was a singer, songwriter, and actor. Kris attended Oxford University on a scholarship and spent the years between 1958 to 1960 there gaining a degree in English literature.

His writing credentials are long and varied with some of his biggest hits being sun by other artists such as Sunday Mornin’ Comin’ Down and Help Me Make It Through the Night. Kristofferson briefly dated Janis Joplin who recorded his song Me and Bobby McGee. When it comes to acting Kristofferson is best known for his role in the 1976 version of A Star Is Born. in 2004 he was inducted into the Country Music Hall of Fame.

The Outlaw: Waylon Jennings

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Waylon Jennings went from playing in a backing band for Buddy Holly to one of the most successful country artists of all time.

Jennings was born Waylon Arnold Jennings on 15th June 1937 in Littlefield, Texas becoming a pioneer of the Outlaw country music movement. by the age of eight he had started playing guitar and left school at 16 and by 21 had completed his first recording session and began playing bass for Buddy Holly. His career spanned over 40 years and allowed him to get to know his fellow Highwaymen in various ways, living with Cash, being involved in the outlaw scene with Willie Nelson, and running in the same circles as Kristofferson. Jennings also composed and sung the theme song for the television show The Dukes of Hazzard and provided the narration for the show.

In 2001 he was inducted into the Country Music Hall of Fame. Waylon Jennings passed away on 13th February 2002.

The Aging Hippie: Willie Nelson

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Willie Nelson, be still my heart and let me explain why he is one of my favorite country artists of all time.

He was one of the main figures of outlaw country, a subgenre of country music that developed in the late 1960s as a reaction to the conservative restrictions of the Nashville sound. Nelson is also very involved in activism including for the use of biofuels and the legalization of marijuana. Willie also helped organize Farm Aid in 1985 to help raise money to benefit American farmers, this is still held annually with Nelson appearing at everyone. He’s a pretty cool cat in my opinion.

He was born Willie Hugh Nelson on 29th April 1933 in Abbot, Texas, and was born during the Great Depression which would greatly influence him politicly and in his song-writing, which he began at the age of seven. Nelson was raised by his grandparents, which again is something I identify with as I myself am very close to mine.

He would begin finding success as a country artist in 50s and 60s but it wouldn’t be until the 70s where his career would really take off. His 1975 album Red Headed Stranger is his most critically acclaimed album while the 1980s would see him release his hit songs On the Road Again and To All the Girls I’ve Loved Before. In 1993 he was inducted into the Country Music Hall of Fame.

We Are The Highwaymen: My Favorite Songs from the American Outlaws

Let’s talk about some of my favorite songs from the group. First up is Highwayman, released in 1985, it is a song written by Jimmy Webb and is about reincarnation. This song was also the inspiration for naming the supergroup of Cash, Kristofferson, Jennings, and Nelson. Since my Grandpa passed it has taken on a deeper meaning to me, especially the last verse sung by Johnny Cash. In the last few years of his life, my Grandpa would occasionally quote to me an old Birdseye advert, normally while we were doing the washing up together.

I’ll 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

(Ghost) Riders in the Sky is my next pick and I originally heard it by Johnny Cash. Written by Stan Jones in 1948 it was originally titled (Ghost) Riders in the Sky: A Cowboy Legend and is a cowboy-styled country and western song. It is considered one of the greatest western songs of all time and I fully agree with this.

It has an ominous feel to it and despite it actually being about ghostly cattle being chased by a cowboy, for me, it evokes visions of the biblical four horsemen of the apocalypse. The Highwaymen version is sung by both Willie Nelson and Johnny Cash, two of my favorite country artists, with their dueling styles and tones bringing something else to the song and creating one of the best versions to date.

A bolt of fear went through him
As they thundered through the sky
For he saw the riders coming hard
And he heard their mournful cry

American Remains, released in 1990 and written by Rivers Rutherford, feels like a spiritual brother to Highwayman. While their first release was about reincarnation this song focuses on the many different men and people of America that have shaped the nation. We start off with a shotgun rider, sung by Cash, which flows nicely into the story of a river gambler, retold by Jennings. After the chorus we get Nelson, singing an impassioned story of a mid-west farmer, which is something he has raised money for with Farm Aid.

I am a mid-west farmer, I make a livin’ off the land,
I ride a John Deere tractor, I’m a liberated man.
But the rain it hasn’t fallen, since the middle of July,
And if it don’t come soon my crops will die.
The bank man says he likes me, but there’s nothin’ he can do.
He tells me that he’s comin’ but the clouds are comin’ too.
He ain’t my friend:
And I’ll ride again.

The last verse talks of a man who is Cherokee, sung by Kristofferson, it explains what this land means to them and how over the years they have seen it destroyed by the people who came from Europe. This verse is so beautiful but I do wish it was sung by Jennings instead. The reason for this is because of his ethnicity, for those who don’t know Waylon is actually descended from Black-Dutch on his father’s side and both Cherokee and Comanche on his mother’s side.

Other songs to listen to are Born and Raised in Black and White, Desperados Waiting for a Train, and Big River.

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