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.”

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Gaining over six million views since uploaded, fans filled the comment section with love and support for both singers. Looking at the comments, they included, “Willie Nelson’s guitar playing is coarse, untrained, rough, and more brilliant than the work of anyone with a PhD in music or the most accomplished trained performers. It is a force of nature made even more wonderful played on that antique nylon string guitar. It is perfect.” Another person added, “This is the only concert I ever attended alone. I had two tickets, nobody else wanted to go with me. You can’t imagine how many people regretted that….”

If you’ve ever been in love, this song (and performance) is bound to strike a chord with you. Emotions have always beautifully seeped through Nelson and Kristofferson’s pen and vocals. However, this performance might take the cake. “Take a moment and listen. “If you have ever loved a woman you will realize this is one of the greatest songs ever written,”  one fan perfectly noted. Another listener added “The most beautiful song of all time. [Kris] may have written it but Willie refined it.”

Willie Nelson Remembers Kris Kristofferson as a “Great Songwriter”

While his legacy continues on, Kristofferson sadly passed away back in September 2024 at 88 years old. Speaking with USA Today about his friend passing away, Nelson admitted, “Kris was a great friend of mine. And, you know, we just kind of had a lot of fun together and made a lot of music together — videos, movies. I hated to lose him. That was a sad time.”

Always taking a moment to shower his fellow country singers and friends with praise, Nelson crowned Kristofferson a “great songwriter.” He continued, “He left a lot of fantastic songs around for the rest of us to sing, for as long as we’re here.”