Imagine sitting down in a room with Kris Kristofferson, Willie Nelson, Johnny Cash and Waylon Jennings.
Known collectively as The Highwaymen, but respected far more for their individual accomplishments, they’re unquestionably four of the best to every play country music.
You can ask them anything you please, and you lead off with an insult? Bold strategy Cotton…
Back in 1991, Paul Holmes, a popular New Zealand broadcaster, sat down with this incredible crew for an interview just prior to their tour.
And he asked if the reason for the tour was that they couldn’t sell any tickets by themselves, or… at least that’s what “critics” were saying:
“Why they’re teaming up together? At least one critic, probably more critics, have suggested it’s because none of you can now fill the holes on your own, it takes four of you.
How do you answer a critic like that?”
Kris Kristofferson jumped in with a chuckle:
“How kind of you to point that out.”
As the rest of the gang joined him in laughing, Waylon joined in:
“Well it’s about time to leave, looks like…”
The four didn’t seem to take too much offense to the comment, and kept it very light, but the insinuation behind the question was pretty insulting to the arguable Mount Rushmore of outlaw country singers.
They quickly put the speculation to rest with Kris Kristofferson starting off the group’s response:
“We have a lot of business being up on stage together because we all have been referred to as ‘wild men’ at one time or other in our life.”
But ultimately, it was the calm and collected Man In Black who corrected these “critics”:
“There’s not a one in this group that can’t fill any hall he plays on his own, that’s not a true statement that you made there.
I haven’t had a show this year, with myself, my wife, and the Carter family that hasn’t been a sellout, and I know Willie sells out every place he plays. So does Waylon, so does Kris. It’s not true that we can’t make it on our own.
As a matter of fact, we have trouble working into our schedule, the shows for The Highwaymen… we do it a year in advance. We’ve taken a year of planning to make this tour happen.”
Waylon followed up Johnny’s poised response with one that is very telling of his own cast-out style:
“I tell ya, one more point too… that if you ask another question like that we’ll burn your home.”
I mean, I know Waylon said that with a grin, but it wouldn’t be the first time he burned down a building. If you remember back in the day, Waylon actually blew up a venue (allegedly) with dynamite after the owner refused to pay them for a gig they just played.
Not to mention, the man has always had a quick wit. If you’re familiar with your Waylon Jennings, this answer won’t come as a surprise to you.
His nonchalant threat had the entire group breaking out in laughter, but realistically I wouldn’t tempt the often-hot-tempered Waylon.
Needless to say, the rest of the interview went more smoothly, and in Paul Holmes’ defense, I think he wanted the guys to clear up the travesty behind the critical statements being made.
His follow up question got into some of the less than glamourous personal details about the four:
“You’ve all been described as survivors, survivors of a collective twelve marriages, more than a hundred and fifteen years on the road, and untold bottles of whiskey and pills… what is he talking about?”
Once again, he seems to be looking for a good quote, but at the same time, you can’t deny the history of these four.
Nevertheless, the two were cornerstones of the outlaw country movement, whether ol’ Waylon liked it or not.
I was going through some of these Mike Judge Tales from the Tour Bus videos, and found this gem of a story, that perfectly depicts how much of an outlaw Waylon was.
In the late ’70s, Jennings transitioned from this clean cut and clean shaven country singer, to the black hat, long haired and bearded country boy outlaw, which many of his friends say was induced by his increasing struggles with substance abuse with cocaine in particular, and his growing weariness of the people in Nashville.
Around that time, fellow country artist Billy Joe Shaver recalled a story about how Waylon always kept some dynamite in the back of the tour bus, just incase it was ever needed.
One night, they were playing a show in this barn, where Shaver said it was packed to the brim, and people were hanging from rafters just to get a good look at arguably the greatest country singer of the time.
Everything was going as planned, until after the show when they were all waiting to get paid.
However, as time rolled on, nobody came out of the barn to pay them, and sure enough they realized they were the last people on the site.
“So we waited and waited and waited, Waylon’s having a fit. Then all of a sudden everybody started leaving… And everybody left. Wasn’t nobody in the place. It was just empty.
And Waylon said, ‘You know, we’ve waited long enough.’ So we get back in the bus…”
Needless to say, Waylon was getting fed up, and he disappeared for a minute and came back, and they all just decided to take off.
Sure enough, as they were leaving, the back half of the barn exploded, more than likely from the dynamite Waylon was keeping in the back of the bus.
“All of a sudden that whole ass end of that club blew up.”