The Highwaymen

The Highwaymen were a country supergroup uniting four of the genre's biggest names: Johnny Cash, Waylon Jennings, Kris Kristofferson and Willie Nelson. Active from 1985 to 1995, the collaboration produced three studio albums, bringing together four already-legendary solo careers, songwriting voices and personas into a single, larger-than-life outlaw-country project.

Their signature song, «Highwayman», a Jimmy Webb composition, became the group's biggest hit and gave the project its name and mythic framing — four men reincarnated across centuries as a highwayman, sailor, dam builder and starship captain. Beyond that title track, the group's catalogue, including songs like «Silver Stallion», «Desperados Waiting for a Train» and «Live Forever», leaned into themes of mortality, freedom and the American frontier, delivered through the weathered, distinctive voices of each member.

As a supergroup rather than a full-time band, The Highwaymen represented the outlaw country movement at its most iconic, each member already having reshaped the genre individually before joining forces. Their recordings remain a touchstone of country music's outlaw era and a rare example of four major solo stars sustaining a collaborative project across a full decade.