On This Date: The Highwaymen’s Iconic Debut ‘Highwayman’ Record Was Topping The Country Albums Chart In 1985

The Highwaymen country music
The Highwaymen/Columbia Nashville

One of the most star-studded projects of all time.

On this date in 1985, The Highwaymen supergroup composed of Johnny CashWaylon JenningsWillie Nelson and Kris Kristofferson peaked at #1 on the Billboard Country albums chart with their first record Highwayman.

After pioneering the outlaw country sound, the four country legends combined to form a group that took the style to new heights, and this record easily became their most popular and successful album.

It was produced by Chips Moman, who produced an insane amount of albums for an insane number of artists, playing guitar on many, along with co-writing some popular songs, including Waylon Jennings’ “Luckenbach, Texas (Back to the Basics of Love)” and Aretha Franklin’s “Do Right Woman, Do Right Man”.

In his 2009 book Willie Nelson, biographer Joe Nick Patoski says the idea was basically to combine the star power of each of them to help rejuvenate excitement, in a sense, about their music and help get them back as mainstays on country radio.

At the time, Willie Nelson was by far the most “relevant” on radio, for lack of a better word, so they figured giving this a shot couldn’t hurt… and they were right:

“The strength-in-numbers collaboration aimed to bolster the careers of four giants old enough to be regarded as legends but who were no longer considered suitable for contemporary country radio.”

In his 1996 memoir Waylon: An Autobiography, Jennings said that they first got together in 1984 while working on an annual Christmas special in Switzerland, and after gathering in a hotel room after filming, they naturally started trading songs (to have been a fly on the wall for that, right).

The rest, as they say, was history:

“John had brought our four personalities together initially, in Montreaux, Switzerland, in 1984.

Every year, he had a television Christmas special, and that holiday season he wanted us all to come over…

We started trading songs in the hotel after we worked on the special, and someone said, like they always do, we oughta cut the album… Usually everyone goes their separate ways after that, but the idea took hold.”

Their debut record consisted of 10 tracks, most notably their #1 hit cover of the title track in Jimmy Webb’s “Highwayman,” in addition to a top 10 version of Guy Clark’s “Desperados Waiting for a Train.”

When you see four of the most recognized and respected icons the country genre has ever seen on one project together, it’s hard to imagine it won’t be a smashing success, and that was certainly the case here.

Highwayman has since been certified Platinum by the RIAA, and continues to be a fan-favorite and country classic to this very day.

One of my favorite things they did together, aside from this album, is their 1990 concert called American Outlaws: Live at Nassau Coliseum, where they joined forces to sing some of their biggest hits and most iconic songs.

They’ve since published tons of the performances for all of us to enjoy today, which we’ve shared many times before, including one of my all-time favorites in Kris Kristofferson’s classic “Help Me Make It Through the Night”:

Turn these up today, and here’s to four of the abolsute greatest that have ever done it, or will ever do it, in Waylon, Willie, Johnny and Kris…

“Against the Wind”

“Desperados Waiting for a Train”


A beer bottle on a dock



A beer bottle on a dock