Introduction

Outlaw Legends Unite: The Highwaymen – A Boy Named Sue (American Outlaws: Live at Nassau Coliseum, 1990)

When four of country music’s most iconic voices—Johnny Cash, Willie Nelson, Waylon Jennings, and Kris Kristofferson—came together as The Highwaymen, it wasn’t just a supergroup; it was living history in motion. Among their most memorable moments is the 1990 performance of “A Boy Named Sue” during American Outlaws: Live at Nassau Coliseum. Though forever tied to Johnny Cash, the song takes on a whole new energy when delivered in the presence of fellow outlaws, each bringing his own grit and character to the stage.

Originally made famous by Cash in 1969, “A Boy Named Sue” is part storytelling, part comedy, and part raw truth. Written by Shel Silverstein, the song’s tale of a boy burdened with an unusual name who grows up tough and confronts his absentee father resonated deeply with audiences. Its mix of humor and hard-edged reality made it one of Cash’s signature numbers. Hearing it again in 1990, surrounded by the camaraderie of The Highwaymen, adds layers of meaning: it isn’t just a story of one man’s fight, but a reflection of the rough, unpolished honesty that defined outlaw country itself.

At Nassau Coliseum, the performance captured the chemistry and brotherhood between these four legends. Cash’s booming delivery carried the weight of the song, while Nelson’s sly grin, Jennings’ baritone presence, and Kristofferson’s poetic aura framed the moment with reverence and mischief. The audience wasn’t just watching a concert; they were witnessing a conversation among giants who had lived the very spirit of the songs they sang.

What makes this particular rendition stand out is how it symbolizes the endurance of outlaw country’s rebellious streak. Even decades after its debut, “A Boy Named Sue” still carried the same punch, laughter, and raw honesty that first made it a cultural phenomenon. In the hands of The Highwaymen, it became more than a hit—it became a celebration of storytelling, resilience, and the unfiltered truth that only country music can deliver.

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