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.
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Dem Vinyl Boyz EP 136 -The Highwaymen - Highwayman
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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.
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