About the Song
“Lovin’ Her Was Easier (Than Anything I’ll Ever Do Again)” is one of the most tender and poetic songs ever recorded by Waylon Jennings, and it stands as a luminous example of his ability to bring emotional vulnerability into the rugged world of outlaw country. Originally written and first recorded by Kris Kristofferson in 1971, Waylon’s version—released in 1971 on his album The Taker/Tulsa—carries the raw honesty of Kristofferson’s lyricism, filtered through Jennings’ smooth baritone and subtle defiance. The result is a performance that’s both intimate and world-weary, full of quiet power.
This song is a reflection, not a lament. It’s the voice of a man who’s experienced love that was so natural, so effortless, that nothing else in life has quite matched its grace. There’s no bitterness here—just reverence, nostalgia, and a deep sense of loss for something that was once simple and pure. Waylon delivers the lyrics with a kind of mellow resignation, never overplaying the sentiment, yet imbuing every line with a lived-in authenticity that only he could summon.
Musically, the arrangement is soft and understated. Gentle acoustic guitar, light rhythm, and steel accents provide a warm bed for the vocal. The tempo moves like a slow walk through memory—unhurried, but emotionally rich. Unlike the rowdy energy of many of Waylon’s outlaw anthems, this track embraces stillness, and it’s in that stillness that the emotion blooms.
One of the most remarkable aspects of Jennings’ interpretation is how intimate it feels. You don’t get the sense that he’s performing the song—you feel like he’s quietly telling it to himself, or to someone he once loved, in the still of night. It’s a song about remembering a love that came without effort, and in its absence, recognizing just how rare that kind of love is.
Though not a chart-topping hit, “Lovin’ Her Was Easier” has remained a fan favorite and a staple of Waylon’s more contemplative catalog. It showcases a side of him that is often overshadowed by the outlaw image: the philosopher, the romantic, the man who understood that strength sometimes lies in gentleness.
In the end, Waylon Jennings’ version of this Kristofferson classic is a masterclass in restraint and emotional honesty. It’s not just a song—it’s a memory, beautifully preserved in melody and voice, reminding us that the simplest things in love are often the hardest to find again.