Introduction
“Loving Her Was Easier (Than Anything I’ll Ever Do Again)” is a song that carries significant weight in the world of country and folk music, primarily due to its deep lyrics and the talents associated with its various renditions. Written by Kris Kristofferson, the song was first released by him in 1971 on his album The Silver Tongued Devil and I. Kristofferson, a prolific songwriter and performer, crafted the song with his characteristic poetic style, combining reflections on love with a melancholic undertone that resonated with listeners across different genres. The song’s success was further cemented when it was covered by The Highwaymen, a country supergroup comprising Kris Kristofferson, Johnny Cash, Waylon Jennings, and Willie Nelson.
The Highwaymen’s version of “Loving Her Was Easier” appeared on their 1990 album Highwayman 2, their second album together. The group, known for its blending of outlaw country style with traditional country and folk elements, brought a unique dynamic to the song. With each member’s voice offering a distinct quality, their rendition highlighted the song’s themes of love, loss, and the enduring nature of heartfelt memories. The arrangement in the Highwaymen’s version emphasized the harmony among the four legendary voices, bringing a different depth to the song while keeping the original emotional essence intact.
Kristofferson’s lyrics reflect the bittersweet beauty of a past love, capturing the ease and naturalness of the relationship. The song discusses the joy found in loving someone and the realization that it was a rare, perhaps even unattainable, kind of experience. It resonates with themes of longing and nostalgia, which were particularly well-suited to the voices of the Highwaymen, who often dealt with themes of life’s hardships and the road’s rugged path in their music.
The Highwaymen’s take on “Loving Her Was Easier” not only pays homage to Kristofferson’s songwriting but also encapsulates the spirit of the group’s collaboration. Their version is a testament to the chemistry among the members and the way they could bring classic songs to life in new ways. The song stands out as a highlight in the Highwaymen’s catalog, serving as a reminder of their ability to transform deeply personal songs into shared musical experiences.