Thirty-two years ago today (March 3, 1990) was an unforgettable day for four of country music’s leading men. It was on that date that Willie Nelson, Kris Kristofferson, Waylon Jennings and Johnny Cash performed at the Houston Livestock Show and Rodeo, kicking off their first concert tour as the Highwaymen.
Cash, Jennings, Kristofferson and Nelson had recorded their self-titled debut album together five years earlier, in 1985, before they were officially a group. That record spawned the No. 1 single “Highwayman,” a cover of the Jimmy Webb classic, which gave the quartet its name. But it wasn’t until Highwayman 2 was released that the foursome hit the road together.
This Highwaymen’s 1990 tour also included a stop in Austin, Texas, at the Fourth of July Picnic at Zilker Park, where they were joined by Shelby Lynne and Asleep at the Wheel. Two years later, in 1992, the four stars hit the road together again, this time overseas; the Highwaymen launched their European tour in Turku, Finland.
The Highwaymen released one more record, The Road Goes on Forever, in 1995, but it did not have any singles that made the charts. Their freshman record was the only one certified platinum, for sales of one million units.
Cash, Jennings, Kristofferson and Nelson each had their own successful careers to maintain while they were touring as a quartet: In 1990, Nelson released Born for Trouble, Kristofferson debuted Third World Warrior, Jennings put out The Eagle, and Cash released Boom Chicka Boom.
The Highwaymen officially disbanded in 2002, after Jennings’ death.
This story was originally written by Gayle Thompson, and revised by Annie Zaleski.
Willie Nelson + More Country Stars Who Have Served in the Military:
WATCH: Unforgettable Johnny Cash Moments