A Revealing Look at Music's Highwaymen

The men themselves would have scoffed at such a title, but when Johnny Cash, Waylon Jennings, Kris Kristofferson and Willie Nelson recorded and toured together as the Highwaymen, what better example of a supergroup? Tonight at 8 pm/ET, CMT premieres American Revolutions: The Highwaymen, filmed by music producer Don Was, a revealing insider's look at the four complex individuals as they recorded what turned out to be their final album, The Road Goes on Forever, in 1994. (Jennings died in February of 2002; Cash in September 2003). TVGuide.com found Kristofferson in Nashville, where he confirmed that Cash's 1984 Christmas on the Road holiday special served as the group's germination.

Kris Kristofferson: We'd known each other, but [Christmas on the Road] was the first time we all worked together, and it was really the beginning of the Highwaymen there, kind of by accident. John had called Willie and said, "I think you've done a duet album with everybody in the world except me." And Willie thought I ought to be there to pitch them some songs. Waylon was there, too, and [producer] Chips Moman decided to have us do "The Highwaymen," that song by Jimmy Webb, and that's how it all got started. It went well, so we did a couple more and the next thing you knew, we had an album.

TVGuide.com: There's a segment in American Revolutions about a certain apprehension that existed when you all pitched songs to each other. Was it a difficult situation when a song was turned down?
Kristofferson: No, we had enough material with all of us to come up with stuff that we all liked. There was no point in doing any that somebody didn't [like]. I think it's kind of odd that [disagreements] didn't happen more, because all four of us were pretty individualistic — we each went our own ways and were used to having to fight to get to do things that some people didn't want us to do.

TVGuide.com: And that's what drew you together?
Kristofferson: Yeah.... Well, I don't know. Those guys all were my heroes before I ever even came to town. I was John's janitor for a couple of years over at the Columbia recording studios.

TVGuide.com: And then, the legendary helicopter incident.
Kristofferson: Yeah, well, that's returned to haunt me. [Laughs] I had known John for a couple of years before I ever did that. I pitched him every song I ever wrote when I was working at Columbia as a studio setup man. At one point I found out I was going to be a father again and I'd be needing some more money, so I joined the National Guard as a helicopter pilot for a while. I decided I'd fly in a tape and get John's attention.... Almost landed on his roof.

TVGuide.com: That tape was "Sunday Morning Coming Down" [which Cash recorded and subsequently won CMA Song of the Year in 1970].
Kristofferson: Well, that's the way John remembered it [along with pilot Kris having "a beer in one hand and a cigarette in the other"]; that's not the way I do. [Laughs] But he did me so much of a favor so many times, I'm willing to go with any story he came up with.

TVGuide.com: Talking about those pitch sessions, you say, "Artists aren't necessarily the most confident people in the world."
Kristofferson: I think that's true. There's a tension about being up in front of people. When your work comes from deep inside of you, that's a very vulnerable position to be putting yourself into, [there] in front of a live audience. And I'm sure that's why at least three of us up there anesthetized ourselves to it. [Laughs] I think Willie's pretty confident; I've never seen him nervous about being in front of anybody. But I know Waylon and John and I were all scared when we'd go out there — not in a bad way, but just because you want to be so good so badly. [Laughs]

TVGuide.com: How often are you in touch with Willie?
Kristofferson: Pretty often. We haven't been working together, but he's got a place out here [in Nashville] — I live in Hawaii — and we get together every now and then, hit a golf ball around. I'm really glad they're coming out with this [documentary]. I really miss those guys.