What do you get when you put four enormously famous country and folk musicians, all of whom are best buds, in a band together? Well, you get The Highwaymen! This group was probably the best country music supergroup of all time. While that’s a bold statement, it’s important to note that this supergroup was made up of the likes of Johnny Cash, Willie Nelson, Kris Kristofferson, and Waylon Jennings. How the band didn’t implode from all that talent, I just don’t know.
The Highwaymen were active between 1985 and 1996, and they put together just a handful of incredible albums. The first of those albums was the simply-titled Highwayman, released in May of 1985. And by August 17, 1985, the album had made it to the very top of the country charts.
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The Enduring Power and Quality of ‘Highwayman’
Highwayman peaked at No. 1 on the Billboard US Top Country Albums chart, and only slipped to No. 20 by the end of 1985. The album also made it to No. 92 on the Billboard 200. It also did fairly well on the Australian charts. It’s considered Certified Platinum today, and while their two follow-up albums did well, Highwayman was the group’s biggest and most successful piece of work.
These four artists were known for their association with the “outlaw country” musical movement. This subgenre of country music came to be back in the 1960s, and had more of a focus on non-traditional country stylings that didn’t really involve pandering to the popularity of trends in Nashville. The music was often about outlaws and cowboys, but the musicians themselves were outlaws in their own right.
Naturally, putting four of the biggest names in outlaw country into one band would garner some attention from fans of the subgenre. And, considering the group was made up of genuine friends, the collaborative process of putting the album together was likely both a breeze and an incredible, boundless pool of creativity. The results of this collaboration certainly prove that.
Highwayman is what happens when four talented musicians who all love each other’s work come together to make something amazing. When one thinks of progressive country, one thinks of this album. Each member traded off vocals, and the whole of the record just sounds like it was meant to be. And even the artists who put this record together were proud of it.
“You wouldn’t think our four uneven voices would blend,” Willie Nelson once said. “But they did. They fit together like a jigsaw puzzle.”
I highly recommend listening to this 10-track album in full.
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