Dem Vinyl Boyz EP 136 -The Highwaymen - Highwayman

In this legendary episode of Dem Vinyl Boyz, we saddle up with four of country music’s most iconic outlaws—Johnny Cash, Willie Nelson, Waylon Jennings, and Kris Kristofferson—as we spin their unforgettable 1985 debut as The Highwaymen. Aptly titled Highwayman, this album wasn’t just a collaboration—it was a supergroup moment that brought together decades of grit, wisdom, and storytelling into one timeless record.

The title track, "Highwayman," became an instant classic, featuring each artist taking a verse as a reincarnated soul traveling through time and history. From the haunting delivery to the poetic lyrics, it set the tone for an album that explores the American spirit, redemption, rebellion, and brotherhood. Other standout tracks like "Desperados Waiting for a Train" and "The Twentieth Century Is Almost Over" offer equal parts reflection and rowdiness, with that unmistakable outlaw flair.

In this episode, we break down the formation of the group, the chemistry between these four legends, and how Highwayman became a defining moment not just for them—but for country music as a whole. It’s an album that honors tradition while forging its own trail across the dusty highways of Americana.

Join Dem Vinyl Boyz as we celebrate Highwayman, an album where four rebel hearts came together and reminded the world what real country sounds like—raw, honest, and unforgettable.

For decades, people who enjoyed music on vinyl records instead of CDs or MP3s were considered dinosaurs. While we like moving at 33 RPM, the rest of the world rushed and went to digital. Not only did vinyl refuse to die but demand is at its highest since at least 1991. It's a good thing Dem Vinyl Boyz saved all their records from back in the day. Because, now we have the biggest collection of 12-inch records on the radio.  Dem Vinyl Boyz love the joy of sliding a classic album out of its cover; the crackle of a needle just dropped into a groove; the careful way to pick up and flip a record when a side ends. On the podcast each week we feature a different piece of music history on vinyl record. Dem Vinyl Boyz experience the album front and back, giving you commentary and music facts along the way. Put your ear buds in and let us take you on a musically journey listening to the greatest music of all time and the history of how it became legendary. Dem Vinyl Boyz! Respect The Technique