The Origin of The Highwaymen

Under any context outside of the music industry, the name “The Highwaymen” would evoke images of the Wild West and outlaw bandits. And, we guess, that is the goal when it comes to the supergroup consisting of Johnny Cash, Willie Nelson, Waylon Jennings, and Kris Kristofferson as well.

Though they weren’t robbing people with a six-shooter, a semblance of the same outcast mentality is found within the band. Each of the individual members has challenged the conventions of country music in one way or another.

Cash proliferated a sense of anti-establishment in the genre. Nelson wears his stoner badge proudly. Jennings was a desperado through and through. Kristofferson tells it like it is.

Without the contributions of these artists, country music would still be subscribed to keeping the peace and quaintly singing about love.

But, how did this supergroup come to be? Find out, below.

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The Origin of The Highwaymen

Each of the members had experienced a successful solo career by the time they decided to join forces in the mid-80s.

According to Rosanne Cash, The Highwaymen were born out of “pure friendship. There was no marketing guy who came and said, ‘This will be a good idea.’”

The idea for the group came from a Cash Christmas Television Special in Switzerland, featuring all four members. In the downtime between filming, the musicians did what musicians do and started jamming together.

The jam session turned into something more with the foursome deciding to make a formal album in 1985. The group earned its moniker through the release of that debut album, Highwayman, which was titled after the Jimmy Webb song of the same name.

The title track became a No. 1 hit on Billboard‘s Hot Country Songs Chart. Other notable tracks include their rendition of Guy Clark’s “Desperados Waiting for a Train.”

From there, the group went on to release two more studio albums: Highwayman 2 and The Road Goes On Forever – all of which have gone down as singular and vital pieces of country music magic.

Their solo careers were so iconic that only their combined star power could even hope to outshine them. But, according to those closest to the foursome, the group was only it because of the admiration and love they had for one another.

“It’s the honesty and the purity of that friendship that made the Highwaymen stand out,” John Carter Cash told Rolling Stone. “Individually, these gentlemen had their own style, their own thoughts, their own feelings, their own emotion. But they came together as friends, and that’s the unifying power of the Highwaymen.”

Shooter Jennings added, “Those guys really loved each other. Because they all came from the same ilk and knew each other and made a career together, they were all close friends. That’s where the magic was. It wasn’t an awkward pairing or like working with someone they didn’t know.”

The Highwomen

In 2016, a group of female artists – Amanda Shires, Brandi Carlile, Natalie Hemby, and Maren Morris – decided to join forces in the same spirit as The Highwaymen. The group decided to name themselves The Highwomen as an homage to the supergroup.

“When we were talking about The Highwomen as a band, one of the first things we tasked ourselves with – was writing that to tell the stories of women and the progress and the regress, I guess, at times,” Shires once shared with NPR. “Brandi started it, and then I swung it back to her, and then she swirled it back to me. And we kept going back and forth until we had it to perfect.”

In the same way that The Highwaymen sang about the plight of the wayfaring man, The Highwomen put women’s issues at the front and center.

Though The Highwomen have quite a ways to go before they amass the same legacy as their namesake, their formation speaks to what The Highwaymen made very clear: there is strength in numbers.

(Photo by Rob Verhorst/Redferns)