“There’s not one of us who hasn’t come face to face with his own mortality, and many’s the time we’ve gone through our struggles and survivals together. There’s a blues song that talks about the ‘key to the highway.’ That’s our friendship, unlocking any door that stands between us, and it keeps four very different individuals together.”
— Waylon Jennings on The Highwaymen
This month we’re getting a mighty commemoration of The Highwaymen, a country music “supergroup” composed of Waylon Jennings, Kris Kristofferson, Johnny Cash and Willie Nelson. PBS is broadcasting a segment of its “American Masters” series titled The Highwaymen: Friends Till the End, premiering nationwide Friday, May 27, at 9/8c on PBS. I have to wait till June 4 for it to hit Oregon Public Broadcasting.
The Highwaymen Live – American Outlaws has already hit the street. It’s a deluxe new 3CD/1DVD (or 3CD/1 Blu-ray) box set of concert performances–including a previously unreleased complete concert on CD and DVD (or Blu-ray).
…the documentary features vintage performances, rare, behind-the-scenes footage of life on the road and in the studio with producer Don Was, and new interviews with Nelson; Kristofferson; family members Jessi Colter (country singer and Jennings’ wife), Annie Nelson, Lisa Kristofferson, and John Carter Cash; band members Reggie Young (guitarist) of The Memphis Boys, Mickey Raphael (harmonica player) and Robby Turner (pedal steel guitarist); and managers Mark Rothbaum and Lou Robin. Artists influenced by The Highwaymen, including John Mellencamp, Toby Keith, Marty Stuart, and Ray Benson of Asleep at the Wheel, are also interviewed. Jennings and Cash add their perspective via archival interviews.
As an excellent Rolling Stone piece notes, The Highwaymen wasn’t a marketing gimmick. This was four good friends — brothers, really — coming together to make music they all loved. All four were men of towering and independent personality. Their take-no-shit attitude applied to each other as well as to the world at large. None of them was the least bit hesitant to speak their mind. They could bump heads and bicker. Waylon did not like Kris using the bully pulpit to preach political sermons. He didn’t share Kris’ lefty politics and in any case didn’t think an artist should use the platform of a concert to proselytize. But respect for the artist and love for the brother trumped any hassles and bridged any divide. There’s an example there.
The Rolling Stone article notes that Jimmy Webb’s “Highwayman” may have been their signature song, but the one they truly embodied was Guy Clark’s “Desperadoes Waiting For A Train.” RS is right on that, and it’s especially poignant to ponder on it with Guy’s death earlier this week. Guy’s gone — so is Cash and so is Waylon.
Emmylou Harris says, “They need to be up there on the big rock with the presidents.” Truer words were never spoken.



Matthew says
I always thought “The Highwayman” was an odd song for a group of country artists to do with it’s themes of reincarnation and space travel. Not that I did not like it. In fact I think they did a very good job with alternating who was singing.
JimC says
Yeah, it is an odd song — but strangely affecting. I can’t tell you the number of folks who “didn’t like country music” that loved that song — and finally “got” my Waylon Jennings obsession.
Matthew says
I know a lot of people who did not listen to country music before Johnny Cash’s come back. I was one of them. Even today people who say they hate country will say they love Cash.
The Highwaymen were basically the four greatest country singers of all time together.
deuce says
Damn, I wish I’d made time/money to see those boys when I could’ve. Loved ’em then, but I love ’em more now. We NEED them more now.