With both singers getting their start during the 1950s, Willie Nelson and Kris Kristofferson appeared to fashion identical careers that saw them dominate the airwaves and silver screen. Outside of leaving their mark on the music industry, Nelson and Kristofferson also appeared in several hit films. Embracing the entertainment industry, the singers also joined forces to create the country supergroup called The Highwayman. Besides Nelson and Kristofferson, the band consisted of other greats like Johnny Cash and Waylon Jennings. Looking back over their successful career, Nelson and Kristofferson once took the stage to perform the classic hit “Loving Her Was Easier.”

Back in 1992, Nelson and Kristofferson walked on stage in Aberdeen, Scotland. Already legendary singers in America, the pair decided to travel overseas to share their love for country music. And with fans packing the arena, the pair produced a flawless duet of “Loving Her Was Easier.”