On This Day in 1985, The Highwaymen Take the Stage for the First Time at Willie Nelson’s Fourth of July Picnic

On this day (July 4) in 1985, The Highwaymen made their first appearance onstage. Willie Nelson, Kris Kristofferson, Waylon Jennings, and Johnny Cash took the stage at Nelson’s annual Fourth of July Picnic in Austin, Texas.

Nelson, Jennings, Cash, and Kristofferson were all cornerstones of the Outlaw Country movement. During the ‘70s, they all blazed their own trails, stuck to their guns, and made some of the best and most influential country music of the 20th century. Their mutual friendship and almost compulsive need to continue creating led them to gather on the stage during Nelson’s annual picnic in 1985.

[RELATED: The Mount Rushmore of Outlaw Country: The Story Behind “Highwayman” by The Highwaymen]

The Unlikely Origins of The Highwaymen

The Highwaymen started after the four musicians flew to Switzerland to record Johnny Cash’s Christmas special. While in a hotel room, playing music and hanging out, they decided to put an album together. The group enlisted Chips Moman to produce.

According to PBS, Marty Stuart, a member of Cash’s backing band at the time, showed the group a song called “The Highwayman” by Jimmy Webb. The song’s four distinct parts made it a perfect fit for the group. It became the first single and title track from the group’s first release.

Interestingly, the group didn’t take on the name The Highwaymen until their third and final studio album The Road Goes on Forever (1995), their final album before Jennings passed away in 2002. Until then, they credited themselves as Nelson, Jennings, Cash, and Kristofferson.

The group would go on to release four compilation albums and a live album.

A Look Back at The Highwaymen’s Chart Success

The group’s first two albums—Highwayman and Highwayman 2—were both produced by Moman for Columbia Records. They reached No. 1 and No. 4 on the Billboard Top Country Albums chart respectively. Additionally, they both made the publication’s all-genre Top 200 album chart. The first peaked at No. 92 and the second reached No. 79. Dan Was produced their third studio album for Liberty Records. The Road Goes on Forever peaked at No. 42 on the Country Albums chart and didn’t land on the all-genre survey.

Their debut single “Highwayman” went to No. 1 on the Billboard Hot Country Songs chart. However, their future singles didn’t fare as well. The other two singles from their debut album—“Desperados Waiting for a Train” and “Silver Stallion”—peaked at No. 15 and No. 25 respectively. The four subsequent singles from their other studio albums failed to chart.

Chart success aside, country fans around the world remember The Highwaymen as the genre’s greatest supergroup.

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