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