Waylon Jennings, Willie Nelson, Johnny Cash, Kris Kristofferson – Highwayman

Highwayman (1985) is a landmark collaboration between country music legends Waylon Jennings, Willie Nelson, Johnny Cash, and Kris Kristofferson — the supergroup known as The Highwaymen. Produced by Chips Moman, the album captures four distinct voices united by mutual respect and timeless storytelling. The opening title track, written by Jimmy Webb, became a number-one country hit and set the tone for the project: rugged, reflective, and steeped in myth. Across songs like “Desperados Waiting for a Train,” “Silver Stallion,” and “Deportee,” the record celebrates resilience and brotherhood through classic American songwriting.

What makes Highwayman remarkable is its honesty — a meeting of giants who bring their own histories and heart to each song without ego. The production is warm and understated, allowing their voices to carry the weight of experience. The album stands as both a testament to country’s outlaw spirit and a moving reflection on friendship, legacy, and time.

Reviews

“The rest of the record lives up to the leadoff hit — timeless songs delivered with grit and grace.” – AllMusic

“A rare supergroup that worked because it was built on friendship and authenticity.” – American Songwriter

“A heartfelt collaboration that captures the enduring spirit of country’s great storytellers.” – Rolling Stone