In the history of country music, few moments carry the weight and magic of seeing Johnny Cash, Willie Nelson, Waylon Jennings, and Kris Kristofferson standing shoulder to shoulder as The Highwaymen. Each man was already a towering figure in American music, but together they became something even more powerful — a living embodiment of the outlaw spirit.
One performance that continues to echo with fans decades later is their live rendition of “Loving Her Was Easier (Than Anything I’ll Ever Do Again)” from American Outlaws: Live at Nassau Coliseum, 1990. Written by Kristofferson in the early 1970s, the song was already a quiet masterpiece. In the hands of The Highwaymen, it became something timeless.
Kristofferson first recorded “Loving Her Was Easier” in 1971, offering a tender meditation on love’s simplicity and grace. At a time when many country songs leaned heavily on heartbreak or bravado, this ballad stood apart. Its power came not from drama, but from honesty — love portrayed as something effortless, natural, and deeply human.
When The Highwaymen brought the song into their live set, it became more than a tribute to Kristofferson’s songwriting. It was an opportunity for four master storytellers to share a single emotional space. Each voice added its own shade: Cash’s deep authority, Nelson’s unmistakable phrasing, Jennings’ rugged warmth, and Kristofferson’s raw sincerity.
The Nassau Coliseum concert in 1990 was a landmark moment. Thousands packed the arena to witness four legends sharing one stage. Between roaring outlaw anthems and familiar crowd favorites, “Loving Her Was Easier” arrived as a moment of stillness — an invitation to listen closely.
Rather than turning the song into a solo spotlight, The Highwaymen passed verses and harmonies among themselves, allowing the performance to unfold as a true collaboration. Willie’s guitar gave the song its gentle current, Waylon’s baritone wrapped it in warmth, Cash’s bass voice grounded it, and Kris — the poet at the center — carried the heart of the original.
The result was both intimate and expansive. American Outlaws: Live at Nassau Coliseum remains one of the most celebrated live albums in country music history, capturing The Highwaymen at their peak. Among its many highlights, “Loving Her Was Easier” stands out for its vulnerability — a moment when four icons set aside their outlaw edge and leaned fully into feeling.
It’s rare for a live performance to feel both personal and monumental. That night in 1990, one man’s song became a shared confession, transformed into a collective masterpiece by four voices that defined an era.