Written and first recorded by Kris Kristofferson (US #26/MOR #4/CAN #21 1971).
Other hit versions by Roger Miller (C&W #28 1971), Tompall & The Glaser Brothers (C&W #2 1981).
From the wiki: “Lovin’ Her Was Easier (Than Anything I’ll Ever Do Again)” is a song written and recorded by Kris Kristofferson for his 1971 album The Silver Tongued Devil and I. Released as a promotional single, Kristofferson’s recording did not chart as a country single, but did crossover to the Hot 100 (#28) and Adult Contemporary (#4) charts.
“The song was also released in 1971 by Roger Miller, who included it on his album The Best of Roger Miller and using ‘Lovin’ Her Was Easier (Than Anything I’ll Ever Do Again)’ as a promotional single in July 1971, charting in the Country Top-30.
“Ten years later, it was recorded by Tompall & the Glaser Brothers for the album Lovin’ Her Was Easier. Their single charted Top 5 on the C&W Singles chart. In 1990, Hank Snow asked the brothers to perform at his tribute show so they reunited for this one night. It was the first time they had performed together as a group in over five years and the last time they would ever again appear on stage together.”
Roger Miller, “Lovin’ Her Was Easier (Than Anything I’ll Ever Do Again)” (1971):
Tompall & The Glaser Brothers, “Lovin’ Her Was Easier (Than Anything I’ll Ever Do Again)” (1981):
Tompall & The Glaser Brothers, “Lovin’ Her Was Easier (Than Anything I’ll Ever Do Again)” live performance (1990):