1985 – THE FORMATION: WHEN FOUR ROADS CROSSED. The Highwaymen came together almost by accident, when Johnny Cash, Willie Nelson, Waylon Jennings, and Kris Kristofferson gathered to record the song “Highwayman.” There was no intention to create a “supergroup.” No grand announcement. They simply stood together for one song—and history decided the rest. The album Highwayman (1985) reflects that spirit. It isn’t polished or flashy. It moves slowly, deliberately, carrying the weight of men who had already lived long enough to stop proving anything. The performances feel calm and settled, as if each voice understands exactly when to step forward—and when to fall back and let the song speak on its own.
The birth of The Highwaymen didn’t come from ambition or strategy. It came from timing. From four lives that had…