The Highwaymen’s Final Years: Breakups, Legacies, and the Lasting Bond Between Nelson, Kristofferson, Cash, and Jennings

The legendary supergroup The Highwaymen—comprising Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson—had an unforgettable impact on the country music world. However, as the 1990s progressed, the group’s touring days began to wind down due to the declining health of Jennings and Cash. While the band was still performing into the late 1990s, their ability to maintain a full touring schedule became increasingly difficult, with both men facing serious health issues.

Despite the physical setbacks, the members of The Highwaymen continued to create music, with each of them maintaining their individual careers. Waylon Jennings briefly joined another country supergroup, Old Dogs, but his health continued to decline, and he passed away in 2002. Johnny Cash followed a year later, passing away in 2003. With the deaths of two of the four original members, the dynamic of The Highwaymen changed forever.

Following the passing of their friends, Willie Nelson and Kris Kristofferson continued their careers and even collaborated on several projects. However, these collaborations were not credited as The Highwaymen, as they did not formally reunite the group.

 One notable example occurred in November 2003, when Nelson and Kristofferson came together for a performance of “Big River,” one of Cash’s songs that he had re-recorded in 1985 with The Highwaymen. The performance took place at a Grand Ole Opry-sponsored memorial concert for Johnny Cash at the Ryman Auditorium in Nashville, Tennessee. It was a poignant moment, filled with emotion, as the surviving members of the group paid tribute to their fallen friends.

While the music industry lost two of its most iconic figures in Jennings and Cash, the legacy of The Highwaymen continued to inspire fans, as the collaboration between Nelson and Kristofferson kept the spirit of the group alive. These occasional reunions, though not as The Highwaymen, served as a reminder of the enduring bond and camaraderie shared by these country music legends. Though the group never fully reunited after the deaths of Jennings and Cash, their music, their collaborations, and the impact they left on country music remain timeless. The Highwaymen’s legacy will forever live on in the hearts of their fans and in the music they created together.