This tune was written, composed, first recorded, and first released by Kris Kristofferson.
Kristofferson is an interesting personality. He earned a Rhodes Scholarship to Oxford University and graduated with a Bachelor of Philosophy in English literature. Raised in a military family, and under no small amount of pressure from his folks, he joined the U.S. Army, was commissioned as a second lieutenant and attained the rank of captain. He became a helicopter pilot and also completed Ranger School. In the early portion of the the 1960s he was stationed in West Germany with the 8th Infantry Division.
In 1965, after his tour in Germany ended, Kristofferson was given an assignment to teach English literature at West Point. Nevertheless, having nurtured a love of music he left the Army to pursue songwriting.
His family disowned him because of his career decision.
He swept floors for a job at Columbia Recording Studios in Nashville where he became acquainted with June Carter. He used that relationship to unsuccessfully pitch recorded tapes of his to Johnny Cash.
He also worked as a commercial helicopter pilot for south Louisiana oil company where he flew helos from oil platforms in the Gulf. He split his time between flying and pitching songs in Nashville with little to show for his efforts. It was sitting on an oil platform that he found inspiration to compose Help Me Make It Through The Night and Bobby McGee.
Finally in desperation Kristofferson landed a helicopter in Cash's front yard to get his attention. After Cash heard Sunday Mornin' Comin' Down - Cash recorded it and in 1970 Kristofferson won Songwriter of the Year for the song at the Country Music Association Awards. The rest was history.
This song was recorded in 1971 and while it was not promoted on country music radio it did climb to number 26 on the Billboard Hot 100.
The Highwaymen performing Loving Her Was Easier (Than Anything I'll Ever Do Again) from American Outlaws: Live at Nassau Coliseum, 1990.....
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