The Highwaymen – Highwayman (American Outlaws: Live at Nassau Coliseum, 1990)

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The Highwaymen Ride Again: A Live Rendition of “Highwayman”
The powerful live rendition of “Highwayman” on “American Outlaws: Live at Nassau Coliseum, 1990” by The Highwaymen isn’t just a song, it’s a legendary collaboration coming alive on stage. To understand this performance, we need to delve into the history of the supergroup itself and the iconic ballad they’re delivering.

The Highwaymen formed in 1985, uniting country music titans Johnny Cash, Willie Nelson, Waylon Jennings, and Kris Kristofferson. Each member was already a heavyweight with a dedicated following. Cash, “The Man in Black,” brought his signature baritone and rebellious spirit. Nelson, with his unmistakable braids and outlaw persona, was known for his smooth vocals and introspective songwriting. Jennings, “The Honky Tonk Hero,” offered his raw, bluesy edge, and Kristofferson, the introspective songwriter, added a poetic touch.

“Highwayman,” the title track of their 1985 debut album, wasn’t written by any of them. Jimmy Webb, songwriter for artists like Glen Campbell and Richard Harris, penned this haunting ballad. The song tells the tragic tale of a romanticized outlaw, a recurring theme in country music. Webb masterfully weaves tales of daring escapes, lost love, and the inevitable capture, all delivered in a melancholic yet strangely beautiful way.

The song resonated with The Highwaymen. Their own careers were built on themes of rebellion and pushing boundaries within Nashville’s often rigid confines. Performing “Highwayman” live became an anthem of sorts, a chance for these country music outlaws to celebrate their shared spirit and legacy.

This 1990 Nassau Coliseum performance captures the magic of The Highwaymen in their prime. Their individual strengths come together, creating a powerful vocal tapestry. The crowd’s roar adds another layer, transforming the song from a ballad to a live declaration of their admiration for these country music giants. “Highwayman” on “American Outlaws” isn’t just a song; it’s a testament to the enduring power of collaboration, legendary artists, and the outlaw spirit that continues to inspire.

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