The Highwaymen’s Epic Clapback: Turning an Insult Into an Iconic Moment!

Imagine sitting in a room with Kris Kristofferson, Willie Nelson, Johnny Cash, and Waylon Jennings—legends in their own right, but together known as The Highwaymen. Though they’re celebrated as a group, their individual legacies in country music are nothing short of extraordinary. These four towering figures have shaped the genre in ways that few others ever could, making them not just icons, but some of the greatest to ever grace the stage.

So there you are, sitting in a room with four of the greatest country legends of all time, and you kick things off with an insult? Bold move, Cotton…

In 1991, Paul Holmes, a well-known New Zealand broadcaster, had the rare opportunity to interview The Highwaymen just before their tour. Instead of easing into the conversation, he asked whether they were touring together because they couldn’t sell tickets on their own—or at least, that’s what “critics” were saying.

“Why are you teaming up? At least one critic—probably more—has suggested that none of you can fill concert halls on your own anymore, and that it takes the four of you together. How do you respond to that?”

Kris Kristofferson, with a chuckle, was the first to respond:

“Well, how kind of you to point that out.”

The rest of the group joined in with laughter, and Waylon Jennings, never one to miss a beat, added his take:

“Well, looks like it’s about time to leave…”

Though the comment could have been taken as a serious insult to these country legends, the group handled it with humor and grace. Despite the insinuation, which was pretty bold given their iconic status—arguably the Mount Rushmore of outlaw country—the Highwaymen kept things light. Kris Kristofferson led the way, putting the speculation to rest with their easygoing response.

Kris Kristofferson jumped in with a light-hearted response: “We’ve got plenty of reasons to be on stage together, considering we’ve all been called ‘wild men’ at some point in our lives.”

But it was the calm, collected Man in Black, Johnny Cash, who set the record straight for the critics:

“There’s not a single person in this group who can’t fill any hall on his own. That’s simply not true. I haven’t had a show this year, performing with my wife and the Carter family, that wasn’t a sellout. I know Willie sells out every place he plays, and the same goes for Waylon and Kris. It’s just not true that we can’t make it on our own.”

Johnny Cash responded calmly but firmly, adding, “In fact, we have a hard time fitting Highwaymen shows into our schedules. We have to plan a year in advance just to make it happen. It took a year of planning to pull off this tour.”

Then, in true Waylon Jennings fashion, he followed Johnny’s poised response with a line that perfectly captured his outlaw spirit:

“I tell ya, one more question like that, and we’ll burn your home down.”

Whoa…

Even though Waylon delivered it with a grin, it wouldn’t be the first time he was involved in such mischief. If you recall, back in the day, Waylon allegedly blew up a venue with dynamite after the owner refused to pay them for a gig. So, when Waylon says it, you can’t help but wonder if there’s a hint of truth behind the joke!

Not to mention, Waylon was always known for his sharp wit. If you know anything about him, that response probably didn’t surprise you. His casual threat had the whole group laughing, though tempting the often fiery Waylon might not have been the best idea.

Thankfully, the rest of the interview went a lot smoother. In Paul Holmes’ defense, it seemed like he was hoping the guys would address the unfair criticism being thrown their way.

Holmes followed up with a more personal question:

“You’ve all been described as survivors—survivors of a collective twelve marriages, more than 115 years on the road, and untold bottles of whiskey and pills… what’s that about?”

It was clear he was fishing for a memorable quote, but you can’t deny the history these four legends shared. Willie, with his quick humor, chimed in:

“That’s just Kris he’s talkin’ about!”

Waylon, never missing a beat, added:

“Yeah, what about the rest of us?”

As for the critics’ speculation about their “lack of individual sales,” the group remained largely unfazed, brushing it off with the confidence of men who knew their worth.

It’s safe to say that this cool, unbothered attitude comes with the territory of being an outlaw—or maybe it’s just what happens when you’ve collectively sold nearly 200 million albums.

So I think the lesson is… if you’re going to be a critic, at least do your homework first..