The Highwaymen’s Surprisingly Saccharin Tour Rider

You all know about The Highwaymen, arguably the greatest supergroup in country music history, and one of the greatest supergroups of any genre ever. Willie Nelson, Waylon Jennings, Kris Kristofferson, and Johnny Cash. We think of these guys as the pinnacle of country music badassery.
They were The Outlaws of country music. Well, Johnny Cash wasn’t technically an “Outlaw,” but he drove a star ship, and that was good enough. They were the Overlords of country music let’s just say. The Mount Rushmore of country music. And they had decided to pair up and ride together to save country music in their day.
Well it turns out that maybe The Highwaymen weren’t as rough and tumble as the leathery reputation they presented to the public would portray them to be. Active for a decade, The Highwaymen launched their reign with a #1 album and #1 song that bore the “Highwayman” name. They also toured together after forming in 1985, and from time to time thereafter.
Recently, well-known Jeopardy game show champion turned Jeopardy host Ken Jennings got his hands on the tour rider for The Highwaymen. It’s unclear how he obtained the rider, but seeing how it’s Ken’s job to deal with certitudes, it’s hard to argue it’s not authentic.
Perhaps you would expect requests for ample beer and whiskey to be on hand on The Highwaymen rider, or perhaps some unusual requests that commonly show up on these things, like Van Halen’s request for all brown M&Ms to be removed.
Nope. While graced with the privilege to be able to request just about anything in the world to be awaiting them back stage when they arrived at a venue, the demand of choice from The Highwaymen was Caffeine Free Diet Cokes, spring water, and fruit.
Perhaps the most hilarious request is made by Waylon for some skim milk, while stipulating of course that it’s for his coffee, lest you think Waylon took it with his Special K. Willie Nelson arguably has the most risque rider, taking his Coca-Cola’s leaded as opposed to the diet, caffeine free version on Waylon’s and Johnny’s request.
Some have surmised that maybe the diet options were for wives or crew. That might be the case, but in truth, since The Highwaymen were older dudes in in their day, they were worried about their health and needed to watch their weight. After he got sober, Waylon suffered from diabetes from eating so much, for example.
In 1988, Waylon Jennings was admitted to the hospital for triple bypass surgery. While in the hospital, Johnny Cash came to visit him, started not feeling well himself, got checked out, and soon he was undergoing coronary bypass surgery too. They had rooms right next to each other in the hospital.
So even though the tour rider for The Highwaymen looks comparatively docile to some of the more lengthy and wild ones we’ve seen from other celebrities, it speaks to where these four men were in their lives and their careers. It also seems to allude that they weren’t divas. They were just regular dudes trying to lose the spare tire … except for Willie, who’s been svelte most of his life.
In the real world, The Highwaymen were more like you and me—regular guys and maybe even a little bit humble. And in some respects, that makes them even more badass than we thought of them before.
Highwaymen Tour Rider:
Johnny Cash
6 Caffeine Free Diet Cokes
6 Coca-Cola Classics
Spring Water
Coffee
Hot Tea w/ Honey & Lemon
Fruit
Fruit Juice
Waylon Jennings
6 Caffeine Free Diet Cokes
6 Coca-Cola Classics
Spring Water
Coffee
Skim Milk (for coffee)
Fruit
Willie Nelson
6 Coca-Cola on Ice
6 7-Up on Ice
Spring Water
Coffee
Fruit
Kris Kristofferson
12 Diet Coca-Cola on Ice
Fruit Juice
Spring Water
Iced Coffee
Fruit

March 12, 2023 @ 8:40 am
Wow. I wonder what that would have looked like for those guys a decade before….
March 12, 2023 @ 8:54 am
Thats a lot of soda. From one vice to the next.
March 12, 2023 @ 9:58 am
Let’s remember this is the late 80s. In the late 80s, you had two choices for non alcoholic beverages: soda and tap water. Bottled water was considered hoity-toity, and a luxury of the rich like Perrier. If you had tea, it was made up in 5-gallon coolers and came in powder form. Orange juice was a frozen slug you added water to and mixed in a Tupperware pitcher. I don’t think folks appreciate just how far beverage choice has come in the last 40 years where now you can get coconut water at every corner store. Among other things, this rider is a sign of the times.
March 18, 2023 @ 4:49 pm
Can’t say I’m surprised. These guys put their time in and changed up their ways. Kudos to them. Their combined tour riders look like half of what the average pop star tour rider has on it, too. I could also see these guys giving away anything unopened and not eaten to their crew and/or venue staff instead of telling them to just throw it away.
March 12, 2023 @ 8:58 am
Skim milk is blue water. Straight garbage. Finally discovered something uncool about Waylon goddamn Jennings.
March 12, 2023 @ 6:21 pm
Sorry RyanPD,
Waylon Jennings can make skim milk cool. What a great line-up, these four bastions of music.
March 12, 2023 @ 8:38 pm
“There’s only one thing I hate more than lying, skim milk. Which is water that’s lying about being milk.“ — Ron Swanson
March 12, 2023 @ 9:15 am
They were old. They had long since given up their rough and rowdy ways.
Waylon had several songs that alluded to just that.
And they were also committed to each other to be healthy enough to appear for all the shows. If any one of them were too sick to appear, that would have called off the show. (OK, maybe if Kris was unable to appear, they could have called Billy Joe or Guy Clark to fill in.
March 12, 2023 @ 9:38 am
Glen Campbell pitched in as the 4th highwayman when Kristofferson had to leave early at the first farm aid.
March 12, 2023 @ 4:22 pm
@glendel–I didn’t know that, but I still think the two that I mentioned fit the whole zeitgeist of the Highwaymen group–which was somewhat raw and rough around the edges. Plus, the Highwaymen performed Shaver and Guy Clark songs. Campbell was more clean and pristine–at least in his stage persona, if not his actual personal life. The only connection Campbell might have had to the group was that he was actually the first to record the song “Highwaymen”–but it had not been released as a single for Campbell and most fans thought it was an original song for the group.
March 12, 2023 @ 9:41 am
I still remember the pic of Johnny eating cake on the ground. It’s not quite as famous as his pic giving the ol’ Bronx Cheer. Both pics have been turned into memes.
Never knew Willie dunk Coke. That is pretty interesting.
March 12, 2023 @ 11:21 am
Fruit? Hmm . . . Ahh, yes! Here it is! Morphine is derived from the FRUIT of the opium poppy. Coincidence?
March 12, 2023 @ 11:27 am
Fruit? For all of them? Well, one thing’s for damned certain, which is these aren’t the same kind of fruits that Elton John requests to be sent to his dressing room.
March 12, 2023 @ 12:22 pm
Seriously?
Come on.
March 12, 2023 @ 5:08 pm
Dude, it’s Oscar’s night, the Super Bowl for gays, and Rocketman was years ago. Make a gay joke about Elvis if you want to be relevant!
March 12, 2023 @ 5:39 pm
No more comments on this thread please. Let’s be adults please.
March 12, 2023 @ 5:42 pm
Trig,
I’m gay myself, I was joking. There’s MUCH worse on these comment sections imho.
March 12, 2023 @ 11:50 am
I am no fan at all of the Rolling Stones, but I do recall a “tour rider” of theirs that I once read that had a request that I subsequently found that I agree with. The rider requested that cheese be available in the dressing rooms, but specified, “no Kraft plastic.” “Kraft plastic” was about the only kind of cheese found in my hometown when I was growing up, but when I got out on my own I discovered the huge differences between “Kraft plastic” and REAL cheese.
March 12, 2023 @ 12:42 pm
If you’re going to bring up my favorite rock n roll band Trigger, make sure you get the facts right. Van Halen did NOT want brown M&M’s. They had to be removed from the bowls. You wrote that they only wanted brown ones. Just making sure you get it right.
March 12, 2023 @ 12:58 pm
I saw the Highwaymen in concert, Wellington, New Zealand back in 1991. Great concert.
March 12, 2023 @ 1:24 pm
Fun fact: the brown M&Ms thing for Van Halen was actually a test to see who read all the paperwork. They took that thing about removing the brown M&Ms in an easy to miss part of the documentation, I am part of the documentation with how to assemble all the stage equipment safely And correctly. So they use the M&Ms to decide if the people putting on the event had gone over all their paperwork thoroughly, and then they knew whether or not they needed to check some of their hardware out to make sure everything was assembled correctly.
March 12, 2023 @ 5:50 pm
In a part of…*
I hate the buttons on my new phone so I use voice to text
March 12, 2023 @ 1:32 pm
Just for the record, Kristofferson has been jacked for a long time, I’ve never seen him looking remotely overweight at all.
March 12, 2023 @ 6:50 pm
Kinda unrelated, but having seen Kris in his later years, he reminds me of Rodney Crowell. Eternal, boyish youth. Not to mention great songwriting.
March 12, 2023 @ 3:37 pm
i am a little surprised no smokes or rolling papers in the rider
Kristofferson was an Oxford boxer and Army Ranger. very physically fit man. look at that wee sexy bastard on the poster for Convoy. he always looked like that
March 12, 2023 @ 3:41 pm
Cocaine Blues ain’t got nothing on the caffeine free Diet Coke ennui.
March 12, 2023 @ 4:35 pm
Merle Haggard escaped or ran away from 17 youth facilities and jail. He is the only one of those aforementioned that spent time in a prison (San Quentin). And he went and did a concert at the jail Johnny paycheck was housed in in Ohio after paycheck shot a guy in a ballroom brawl, just because johnny was his friend. If that is not an outlaw then I’ll kiss your ass!
March 12, 2023 @ 8:05 pm
Haggard said that he was ‘housed” in San Quentin when Johnny Cash performed there.
That would have been a performance that occurred years before Cash appeared there in 1969 and recorded his “Live at San Quentin” album–from which his biggest-ever single, “A Boy Named Sue,” was derived–as Merle was already a country music star by that time.
March 12, 2023 @ 10:34 pm
Johnny played San Quentin January 1, 1958.
March 13, 2023 @ 2:47 am
“In the real world, The Highwaymen were more like you and me—regular guys and maybe even a little bit humble.”
Exactly the impression I got from them whether performing together or solo… and whenever I heard them interviewed…
And I would surmise Cash’s request for hot tea with honey and lemon was to sooth aching vocal chords…
March 13, 2023 @ 4:28 am
Their rough and rowdy days behind them, all they wanted to do in the end was make music. I’m now two years older than Cash was when they did this, and I totally get it.
March 13, 2023 @ 8:24 am
But how come no coffee (for the skim milk?)
March 13, 2023 @ 6:22 pm
Good catch!
March 13, 2023 @ 8:28 am
A lot has been made of the “brown M&M” thing. From the research I’ve done, that wasn’t to be divas or anything like that. Bands not only have hospitality riders, most-especially “big” acts-have technical riders also-PA requirements, that sort of thing. The M&M’s were a test-if a promoter/venue/etc cared enough to remove all the brown M&M’s, chances were good that they cared enough to fulfill the sound requirements.
March 13, 2023 @ 1:32 pm
More likely, one of the guys wrote it in as a goof or a joke.
It hardly seems like a grand strategic move, as anybody who read it was likely to just ignore it as being unintelligible.
March 13, 2023 @ 1:42 pm
Yes, I’ve had people pointing this out to me ever since I posted the article. The reason I cited that instance is because it’s one of the more famous rider requests. That one may have had a deeper motive, but for sure musicians have been requesting strange things over the years that make The Highwaymen’s rider look comparatively tame.
March 13, 2023 @ 2:15 pm
Corn bread and ice tea took the place of pills and 90 proof…..
March 13, 2023 @ 6:24 pm
I had to google svelte.
Top 10 post ever because it makes me happy. I’ve been listening to these men for so long. They feel like distant relatives.
March 13, 2023 @ 11:34 pm
Svelte is a Swedish rye bread.
March 16, 2023 @ 7:35 pm
I wrote the rider, with input from the boys. This only shows the dressing rooms, yes we did have requests for stage, meals etc. The most controversial thing was food for the 6 buses at the end of the night. (Pizza, chicken or sandwiches.) There was no alcohol at all. Jay Dauro, Production Manager, The Highwaymen
March 17, 2023 @ 5:47 pm
Had the privilege to be backstage at one of the Highwaymen shows. Pretty laid-back & mellow situation. No drama. Spent some time chatting with June Carter during the show. A very sweet lady.
One of the most memorable concerts I’ve ever seen. Not so much for the performances which were pretty much standard and what you’d expect from each singer. But when they traded verses on some songs and to see them all sharing the same stage – now THAT was something.
March 18, 2023 @ 2:22 am
According to Waylon’s Autobiography, just prior to 1985 is when Waylon got off the pills and coke for good after Jesse’s intervention and his run ins with the feds. So during their Highwaymen run, I imagine they were more conscious on lifestyle changes that had to he made minus Willie whom I’m now convinced is an alien.