3 of the Best Live Performances Where Willie Nelson and Kris Kristofferson Played Side-By-Side

Friends, bandmates, and fellow songwriters are just a few of the names you can tag onto Willie Nelson and Kris Kristofferson’s tight-knit relationship. The two rose to fame together, their families grew up together, they grew old together, and their friendship is one that every human being strives for. That being so, their bond flourished when they were on stage, as one could tell their chemistry was never rehearsed or practiced. Rather, it’s their natural affinity for each other that did all the work for them.

Videos by American Songwriter

Following Kristofferson’s recent passing, it seems between Lukas Nelson’s comments and Willie’s long-time relationship with Kristofferson, that their family has been left devasted. Rightfully so, as the two shared something that transcended far beyond music. However, their performances together were something magnificent in and of themselves. So, here are three of the best live performances between the two great friends.

1. Their Duet of “Loving Her Was Easier(Than Anything I’ll Ever Do)”

When the two were members of The Highwaymen, they performed this song a plethora of times. Originally written and recorded by Kristofferson in 1971, when the country supergroup joined this became one of their staple hits. And it was all due to the chemistry between Kristofferson and Nelson.

Sung as a duet, Nelson and Kristofferson’s rendition of the song is a perfect balance between musical talent and lyrical profoundness. Nothing about Nelson’s guitar licks overshadows the subtextual nuance of the song and vice versa. That said, Nelson offers another layer of color to the song by bolstering Kristofferson’s witty yet melancholic lyrics, and as a result, provides listeners with a spellbinding song bound to leave one in a trance.

2. Nelson and Kris Kristofferson’s Version of “Me and Bobby McGee”

Performing at the Willie: Life & Songs of an American Outlaw, A Willie Nelson All-Star Concert Celebration in Nashville, Kristofferson, Nelson, and Eric Church busted out Kristofferson’s most famous song—”Me and Bobby McGee.” Performing in 2019, Kristofferson and Nelson were on the older side, to say the least. However, that is the beauty of this performance.

Yes, the two country music legends did play the song exquisitely. Although, what is so awe-inspiring about this performance is that one can see and read into the decades-long relationship between Nelson and Kristofferson. Despite being a bit older, the two seemingly weren’t even the slightest bit sick of performing this song for what was probably the 500th or so time. It goes to show that the two were more than just co-workers and they never were bored of each other’s company.

3. “Amazing Grace” With Jimmy Carter

Kris Kristofferson and Willie Nelson are the type of musicians almost everybody can get under. With that in mind, one person in particular who loved their music was none other than Jimmy Carter. Carter and his wife, Rosalyn, joined the two Texas natives on stage at Chastain Park to sing “Amazing Grace.” Now, there is nothing necessarily musically grand about this performance. But, the moment articulates the magnetism Kristofferson and Nelson’s relationship obtained throughout the United States.

In essence, the performance was as American as apple pie and baseball. However, it wouldn’t have been if it wasn’t for Kristofferson and Nelson’s on-stage presence. The performance reminded everybody of Nelson and Kristofferson’s value to American culture, and having Jimmy Carter on stage reinforced the notion that much more.

Photo by Rick Diamond/Getty Images for Essential Broadcast Media