No friendship is always sunshine and rainbows, and a friendship where you work together will likely hit a few more bumps along the road. No group knew how to hash it out and still hug each other after disagreeing more than the famed country supergroup, The Highwaymen.
Over the weekend, Kris Kristofferson passed away peacefully at 88, making Willie Nelson the group’s only surviving member. The sad news is making country music fans take a walk down memory lane, reveling in Kristofferson’s success, including his time as a member of The Highwaymen.
The Highwaymen are unquestionably most notable country super group to ever come along. Composed of Waylon Jennings, Willie Nelson, Johnny Cash, and Kris Kristofferson, the friendship these men had off stage shined through on the stage.
The son of Johnny Cash and June Carter Cash, John Carter Cash, once spoke to Rolling Stone about how friendship made them stand out among other groups:
“Yes, they are THE country supergroup, but it was founded by friendship. And it’s the honesty and the purity of that friendship that made the Highwaymen stand out. Individually, these gentlemen had their own style, their own thoughts, their own feelings, their own emotion. But they came together as friends, and that’s the unifying power of the Highwaymen.”
And while fans felt the magic of that friendship wholly when the men were on stage, that did not always mean they saw things the same way. Waylon Jennings and Kristofferson often butted heads as they did not view using their platform to speak on specific topics the same way. Waylon was an outlaw through and through, and Kristofferson (while he still partook in some outlaw antics) was more of an activist.
“Kris was very much into politics. Waylon never believed that you should use that platform of entertainment (for that), so that really chafed him, but he understood Kris, and Kris understood him.”
In that same interview, Jessi Colter spoke on Jennings and Kristofferson’s relationship:
“Kris was always crazy about Waylon. Waylon was knocked to his knees when he first heard Kris’s songs. They were hanging out in L.A. . . . and then Kris comes to Nashville, and we’re all hanging out on 19th Avenue, driving up and down the streets at night, playing pinball at Bobby Bare’s.
It was a loving thing when Kris and Waylon got together, but onstage, when Kris would talk politics, Waylon wouldn’t agree.”
Because Kristofferson was not afraid to voice his opinion on stage, it often led to disagreements. It’s hard to have four very individualistic men on stage and have one speak about sensitive topics as if they all had the same viewpoint. Even if they had the same perspective, Jennings always believed that the stage was not the right location to preach that message.
“We came very close a couple of times to punching it out. I didn’t say he was all wrong. The main thing I was saying is that he shouldn’t have been doing it on stage, especially with three other people on there who didn’t share all of his thoughts.”
Jennings said during an interview for Kris Kristofferson: The Counter-Culture Hero documentary. While Jennings talked about how he and Kristofferson disagreed for the documentary, Shooter Jennings recalled that it was not just his father and Kristofferson getting into disagreements.
“My dad and Cash would get in a fight and not talk, or they’d get mad at Willie cause Willie had one more song than everybody else. They were like brothers up there, bickering with each other.”
Looking back on those times of disagreement, though, it only strengthened their bond. Although they might have fought with each other often, it wasn’t because they didn’t care about each other or the group’s future. The root of the arguments was more about how to make themselves better and more successful.
I hope Kris Kristofferson has reunited with Waylon Jennings and Johnny Cash up above and are looking back on those squabbles with a grin.
Absolute legends… RIP Kris.
