Kris Kristofferson – Loving Her Was Easier (Than Anything I’ll Ever Do Again)

When Kris Kristofferson wrote Loving Her Was Easier (Than Anything I’ll Ever Do Again) in 1971, he was already making his mark as one of country music’s most literate and poetic songwriters. Released on his second album, The Silver Tongued Devil and I, the ballad quickly became one of his signature works, showcasing his ability to blend intimacy with plainspoken truth.

The song paints a picture of love as something natural and effortless. Unlike Kristofferson’s more rugged outlaw narratives, this lyric leans on tenderness—waking beside someone, the quiet comfort of touch, the peace of being fully understood. Its refrain, “Loving her was easier than anything I’ll ever do again,” became one of the most quoted lines in his catalogue, simple yet profound in its finality.

Commercially, the track was one of Kristofferson’s bigger crossovers. His recording reached the Billboard Hot 100 and Adult Contemporary charts in 1971, exposing him to audiences beyond the country world. At the same time, it was embraced by peers: Roger Miller, Tompall & the Glaser Brothers, and even Willie Nelson would later perform or record their own versions. Its universal theme meant it lived comfortably both in honky-tonks and on pop radio.

For Kristofferson, the song reinforced his reputation as more than just a writer of gritty narratives like Sunday Mornin’ Comin’ Down. He could also be tender, reflective, and direct. In a career that balanced music with acting and activism, Loving Her Was Easier stood out as one of his most personal songs, a timeless ballad about love stripped of complication.

Quick Facts & Trivia

• Written and recorded by Kris Kristofferson in 1971 for The Silver Tongued Devil and I.
• Charted on the Billboard Hot 100 (peaking at No. 26) and the Adult Contemporary chart.
• Roger Miller also released it in 1971; Tompall & the Glaser Brothers scored a hit with their version in 1981.
• Kristofferson was once quoted as saying the song reflected the gentler side of his songwriting, contrasting with his “outlaw” image.
• At the time of its release, he was also gaining fame as a writer for others—Janis Joplin had posthumously taken his Me and Bobby McGee to No. 1 just months earlier.
• The title, long and reflective, became a bit of trivia itself—often cited as one of the longest hit song titles in country music.

Music video by Kris Kristofferson performing Loving Her Was Easier (Than Anything I’ll Ever Do Again). (C) 2007 Sony Pictures Television, Inc.