Introducing, The Highwaymen

Did you know that metrics show that Tuesdays and Thursdays are the optimal days to release a newsletter? What a fool I was to publish the first one on a Saturday! At least we're all on the same page now.

For today's post, I want to reflect a bit on some design work I've been doing. A few weeks ago, I started tooling around with a one-page RPG. A little while later, I realized my work had lined up perfectly with the window for the always exciting One Page RPG Jam. So, this past Sunday (lots of days of the week in this post), I released The Highwaymen, a country music RPG for a dealer, a deck of 52 cards, and 1-4 players.

In The Highwaymen, you play as the Highwaymen, an elite team of outlaw operatives who are actually all reincarnations of the same eternal being. To some, it may be obvious, but the game is inspired to say the least by the country music supergroup The Highwaymen and their quintessential track, "Highwayman." Written and first recorded by Jimmy Webb in 1977 and later covered by Glenn Campbell in 1979, the song's 1985 rendition by Willie Nelson, Kris Kristofferson, Waylon Jennings, and Johnny Cash remains the most famous and most acclaimed, winning the 1985 Grammy for Best Country Song.

The ballad is as high concept as it is simple in execution. Once there was a bloodthirsty highway robber. Hanged, he was reincarnated as a sailor who was lost at sea, a dam builder who was interred in concrete after a tragic tumble, and eventually a starship captain making his way from one end of the universe to the other. "Perhaps I may become a highwayman again," Cash croons. "Or I may simple be a single drop of rain. Unlike many other outlaw ballads, there's a de-escalation of violence and misery that animates the narrative. Across his lives, the Highwayman grows more contemplative and inquisitive.

Now, if one wanted to translate that story into an RPG, the most mature approach might end up looking like Tim Hutching's excellent solo journaling game, Thousand Year Old Vampire. But while the stories to tell there might be interesting—and I'm keeping some mechanical ideas for that sort of thing on the back burner for now—I think the song itself already accomplishes that melancholy tone. For my money, adaptations are always more interesting when they strike a distinct and different chord than the work from which they're derived, which already exists in its own form. Kubrick's The Shining is made more singular because it paints a similar picture using very different colors than King's book.

So I went for silly instead of somber, and I packed the game full of jokes and references, like titling one scenario, after Kris Kristofferson's own ballad, "Help Me Make It Through the Night... Of the Living Dead!" Who doesn't love a genre scramble? Especially if the session is set on—here the game's dealer draws another card—a space station.

The game was also a fun experiment for me in designing an RPG without dice. I'm not totally sure the blackjack-inspired action resolution mechanics hang together—and I've got some new ideas for an expanded system if I ever decide to expand the one-pager into a zine-length game—but it felt so thematic (as Western RPGs from Dust Devils to Deadlands have shown before), I couldn't help but try. If you have the chance to play, do let me know what you think!

Still, while I consider myself a country music fan, the real reason I wanted to make an RPG about the song "Highwayman" is because I've always personally felt the song had a strong connection to playing games. My introduction to the track didn't come from a radio station, but from YouTube, and not from the official music video, either.

When I was a kid (and I promise all of these posts won't be about my Gaming Childhood—although that might make for an interesting feature, down the line) I was hugely into World of Warcraft (which, I should mention, is nowadays owned by Microsoft, whose complicity in and technological support of the ongoing occupation and oppression of Gaza has led the Boycott, Divestment and Sanctions organization to call for a boycott of their products)

Back then, I, Patrick, was that 10 year-old in your Ventrilo server. Not the one who threw slurs around, but the pleasant one, who only occasionally got huffed when a /need roll for purple loot didn't go his way. And just like kids today, I'm told, with their Roblox streams and Fortnite parodies, I was really into what was back then called machinima, a mouthful of a word for something so ubiquitous today it hardly justifies definition. My introduction to "Highwayman" was therefore this video by filmmaker Cranius, now so vintage that its widescreen re-upload to YouTube is old enough to drive a car.

Beneath the video you'll find the usual kind of comments that accompany something like this: meditations on the passage of time (some of them now as old as the video was for the commenter when the post was made), tributes to friends long gone, bitter condemnations of the present state of the world... of Warcraft.

The video itself holds up pretty well, too. It's an artful, if fairly straightforward and literal, representation of what the yarn the song spins might look like if it had taken place in Azeroth. The roads the highwayman prowls meander through the plains of Westfall, while the construction project from which the builder falls is Stonewrought Dam in Loch Modan. Or it used to be. Since the Cataclysm expansion was released in 2010, the dam itself has been a wreck of rubble.

Today, the whole thing reminds me of that special creative energy that once surrounded WoW, something so totally distinct from today's hustle for virality that it's hard to believe stuff like "Highwayman"—or, another old favorite, a video for "Weird Al" Yankovic's "Hardware Store" by Harribo (aka Slegg, level 60 Rogue) and Dav3 (aka Maere, level 60 Mage)—were simply made by enthusiasts, for enthusiasts, unmarketed and unmarketable, with little hope for serious revenue, but out of love for the game, its world, and its community. People should absolutely profit from their labor but, I dunno, sometimes I think the vibes used to be better!

In any case, the "Highwayman" video was released sometime near enough to the release of Batman: Arkham Asylum, that when I rented that game from Blockbuster and played it through one weekend, the song, stuck in my head ever since watching, was as much a companion to my version of Batman as Oracle or Alfred. I remember imagining Bruce's suit coming equipped with speakers, blasting the ballad as he beat goons into miraculously un-bloodied pulp.

To this day it's impossible for me to separate the song from the video, and thereby from the game that inspired it and inspired me to find it. The WoW-"Highwayman" connection, suffice it to say, left a lasting impression on my brain. So when I finally realized that an RPG would be just the thing to scratch that age old itch, I went for it! The Highwaymen (Fiorilli, 2025) is the result. Which will you choose?

Data also shows that you should end newsletters with a call to action or question for engagement. So consider subscribing, if you haven't, so that your Tuesdays (or Thursdays?) will be that much better for it, and let me know: do you have any strong associations tying a game to an otherwise unrelated song?

POF