In the rich tapestry of country music history, few images are as iconic—or as powerful—as Johnny Cash, Willie Nelson, Waylon Jennings, and Kris Kristofferson standing side by side as The Highwaymen. Already legends in their own right, these four men brought decades of storytelling, grit, and soul to the stage. But together, they became something more—a true force of American music.
Among their many unforgettable performances, one stands out for its grace and quiet power: “Loving Her Was Easier (Than Anything I’ll Ever Do Again)”, performed live at the Nassau Coliseum in 1990.
A Song from the Heart
Originally written and recorded by Kris Kristofferson in 1971, “Loving Her Was Easier” stood apart from the honky-tonk heartbreak of the era. It wasn’t a song about pain or loss—it was a song about peace. A song about love so natural and effortless, it felt like breathing.
Kristofferson’s lyrics painted a picture of emotional simplicity, framed in poetic honesty. When he first recorded it, the song resonated deeply. But when The Highwaymen performed it live nearly two decades later, it became something timeless.
A Historic Night at Nassau
The 1990 Nassau Coliseum concert—later released as part of American Outlaws: Live—was a landmark moment. Thousands of fans packed the arena, drawn to the rare sight of four country giants sharing one stage.
Between outlaw anthems and roaring crowd-pleasers, “Loving Her Was Easier” offered a pause—an emotional exhale. It was a moment of deep reflection that contrasted the group’s usual rugged bravado.
Each member brought something uniquely theirs to the performance:
- Willie Nelson‘s smooth guitar work and gentle phrasing gave the song its natural flow.
- Waylon Jennings added warmth and richness with his signature baritone.
- Johnny Cash, ever the anchor, grounded the performance with his deep, resonant voice.
- And Kris Kristofferson, the song’s creator, delivered it with raw, poetic sincerity.
Rather than one man taking the spotlight, the performance was a shared moment. The verses passed between them, harmonies rose and fell, and four voices became one. The chemistry was undeniable.
A Legacy of Vulnerability
What makes American Outlaws: Live at Nassau Coliseum so special isn’t just the music—it’s the vulnerability. It’s rare for a supergroup to step back from ego and let emotion lead. Yet that’s what The Highwaymen did.
“Loving Her Was Easier” wasn’t just a song in their setlist—it was a statement. A reminder that behind the legends, the grit, and the outlaw image, there were men who knew love, loss, and tenderness.
That night in 1990, they didn’t just perform—they connected. With each other, with the song, and with every heart in the audience.
A Timeless Moment
More than 30 years later, this performance still resonates. It’s a masterclass in restraint and soul, proving that true greatness often lies in simplicity.
If you’ve never seen it, do yourself a favor: Watch The Highwaymen’s “Loving Her Was Easier” (Live at Nassau Coliseum, 1990). It’s not just a concert moment—it’s a piece of music history. And if you’ve already seen it? Watch it again. Some things only get better with time.
