On This Day: The Highwaymen Take the Stage for the First Time in 1985

by Clayton Edwards

In America, we celebrate our country’s birth on the Fourth of July. We light fireworks, fire up the grill, and gather to celebrate the freedoms we have. However, country music fans have even more to celebrate. Today marks the first live appearance of the greatest supergroup in the genre’s history. On this day in 1985, the Highwaymen took the stage for the first time.

After performing at the poorly-advertised Dripping Springs Reunion in 1972, Willie Nelson decided to hold his own summer party. The next year, he held his first Fourth of July Picnic. Since then, the annual fundraising event has become one of the cornerstones of summer for country fans in the Lone Star State and beyond. 37 years ago today, the Highwaymen took the stage for the first time during Willie’s picnic, according to Kris Kristofferson Fans.

The Highwaymen Didn’t Have a Name in 1985

Willie Nelson, Kris Kristofferson, Waylon Jennings, and Johnny Cash took the stage together at Nelson’s Fourth of July Picnic. At that time, however, they weren’t calling their group The Highwaymen. Instead, they were listed by their individual names.

Whether they called themselves the Highwaymen or just went by their names, there’s no denying the power of the supergroup. Willie Nelson, Kris Kristofferson, Waylon Jennings, and Johnny Cash are legends. Between them, they’ve written, recorded, and released some of the most enduring country music in the genre’s history. At the same time, they were all friends. As a result, they had just as much chemistry as talent while playing together.

A Brief Timeline of the Supergroup

The group that would come to be known as The Highwaymen took the stage for the first time on this day in 1985. However, it was far from the first time they had worked together. Waylon and Willie were longtime collaborators as were Johnny and Kris. More than that though, the foursome had already been in the studio together before their appearance on that hot July day. The group’s debut album Highwayman dropped in May of 1985.

Their debut record spawned two singles. The Jimmy Webb-penned title track topped the country chart. Later, the group’s cover of Guy Clark’s “Desperados Waiting for a Train” reached number 20 on the country songs chart.

In 1990, the group released Highwayman 2. This album cracked the top five on the Billboard Country Albums chart. Additionally, the group’s sophomore release brought them a Grammy nomination for Best Country Vocal Collaboration.

It wasn’t until 1995, with the group’s third and final record, The Road Goes on Forever, that they finally took the name The Highwaymen.

While The Highwaymen didn’t release any more albums, they continued to tour into the late nineties. By that time, both Waylon Jennings and Johnny Cash were slipping into poor health. Waylon passed away in 2002 followed by Johnny in 2003.