The Highwaymen – “Loving Her Was Easier (Than Anything I’ll Ever Do Again)”

The Story Behind the Song

Some songs capture not just a love story, but the very essence of love itself—the joy, the peace, the bittersweet ache of remembering what once was. “Loving Her Was Easier (Than Anything I’ll Ever Do Again)” is one of those rare songs. Written by Kris Kristofferson and later carried into eternity by The Highwaymen—Johnny Cash, Willie Nelson, Waylon Jennings, and Kristofferson himself—it became more than a ballad. It became a meditation on love’s simplicity and its irreplaceable power.

The roots of the song reach back to Kris Kristofferson’s poetic soul. Known for his rugged voice and even more rugged honesty, Kris had a way of writing lyrics that felt like pages torn from a diary. In the late 1960s and early ’70s, he was living the restless life of a songwriter and dreamer, often reflecting on fleeting romances and the kind of tender connections that linger long after they’re gone. “Loving Her Was Easier” was his way of bottling that feeling—the quiet beauty of being completely at peace with someone, if only for a while.

When The Highwaymen came together in the 1980s, blending four of country music’s most iconic voices, the song took on a new meaning. No longer just one man’s reflection, it became a shared testimony—four men who had lived through fame, heartbreak, triumph, and regret, now singing together about the one thing they all knew: the memory of true love never fades.

For older listeners, the song carries a special weight. By the time we’ve lived a few decades, we all carry our own version of “her.” She might be a first love, a lost love, or a partner who walked with us for years before life took her away. The Highwaymen’s version reminds us that no matter how much the world changes, that memory—the ease, the peace, the completeness of loving someone truly—remains unmatched by anything else we will ever do again.

The arrangement itself is simple, almost hymn-like. No theatrics, no gloss—just voices seasoned with age and experience, weaving together to deliver the truth. Willie’s gentle phrasing, Johnny’s deep resonance, Waylon’s rugged baritone, and Kris’s weathered honesty combined to create a performance that felt less like a song and more like a prayer.

When fans heard it live, the effect was profound. The crowd didn’t cheer wildly; they listened. Couples leaned closer. Older fans wiped their eyes. And many walked away reminded of someone they had loved and lost, carrying that bittersweet ache in their hearts once more.

That’s why “Loving Her Was Easier (Than Anything I’ll Ever Do Again)” endures. It isn’t about youth or fantasy—it’s about memory, truth, and the quiet recognition that some loves cannot be replaced. For The Highwaymen, it was a song of wisdom; for the rest of us, it remains a mirror of our own most tender memories.

Because the truth is simple: in a lifetime full of work, struggle, and change, loving her—whoever she was—will always stand as the easiest, most beautiful thing we ever did.