Doing a Cool Move

My roommate ty asks an important question of each game he plays. The question first emerged, I believe, during hours-long sessions of mid- to heavy-weight board games (Oath, Twilight Imperium, the big crunchy League of Legends board game, several unusual David Sirlin titles), many of which were a struggle in one way or another. The question is this:

How hard is it to do a cool move in this game?”

Let’s consider this question in some common games:

  • In chess—a game I am not at all an expert in, but have spent a lot of time watching the chess hustlers play in Union Square—a cool move” is mostly about making your opponent miss a key observation. Chess players start to lose when they fail to notice an important play, often many moves in advance. They blunder a knight, accidentally land in check out of nowhere, or make suboptimal trades. Thus, a player’s cool move is to see this possibility in advance, slip past their opponent, and pounce on the weakness. Very cool.
  • In tag, a cool move is about physically moving. You duck or twist past your friend who’s it, you make a daring leap across the playground stucture, you make some mad sprint over long distance to escape. It’s cool because you’re physically doing it. Awesome.
  • In poker, a game I also don’t know very much about (but I have been reading Frank Lantz’s book, which often discusses poker), a cool move is always about bluffing. It’s about fooling and deceiving your opponents, one way or another, to get them to buy into your con. You read them, you hook them and reel them in, and then you take their money. So exciting and compelling there’s a whole James Bond climax that’s just Bond and Mads Mikkelsen playing poker, both of whom make some very cool moves.
  • In Titanfall 2, a cool move is about precise timing, reflexes, 3D spatial maneuvering, and understanding how to exploit a videogame’s character controller. You bunnyhop, wall-run into a double jump, achieve max speed, then whip around two-hundred-and-seventy degrees with the grappling hook and land a cross-map sniper rifle headshot, all in mere seconds. It’s difficult to master, but beginners start trying cool moves very quickly, and learn the good ones as they play.
  • In a Dark Souls speedrun, a cool move is about extreme manual dexterity and combat mastery intermixed with exploiting glitches and quirks in the game, plus a total understanding of the environments and levels design. Every speedrun gets strange quickly, but runners make bizarre and fascinating moves as they play. Jumping off a would-be lethal cliff to survive, glitch the camera at an impossible angle to convince the game you’re dead, and thus clip through boss gates? Very cool.

For a move in a game to be cool, it has to be unexpected or unpredictable in some way—surprise is an important element of a cool move. Whoa! Wild! Check it out! I exclaim to my group chat as I post the latest trickshot compilation. We love to be surprised and amazed by what we can do in a game.

A cool move is also powerful. A cool move demonstrates mastery, understanding, or talent, even on the small scale. A cool move to a total beginner is different than a cool move made by a highly experienced player—what starts as cool becomes normal, and the cool horizon expands further. When you start playing fighting games, a quarter-turn seems like some impossible task; for players climbing the ladder, the question stops being if you can do the move but rather when you deploy each of your many cool moves (including the humble quarter-turn).

Fresh and unexpected action combined with a high degree of skill together demand an open playing field, a relatively broad state space. For every cool move, there needs to be a larger field of uncool moves: regular moves, boring moves, average moves. Perhaps to a new player, every move of the experienced player might look cool, but for the experienced players there always needs to be that horizon to chase, new levels of unexpected prowess to seek.

Many games tighten this horizon in order to raise the floor. When I play, say, Assassin’s Creed, my basic attacks turn into long, flashily-animated combo chains as my dude rips through the mobs, all just by me pressing X, X, X over and over again. It looks cool, sure, but it doesn’t feel cool. I know anybody who plays Assassin’s Creed could make the same moves, since it takes next to no talent. That level of guaranteed cool” often reduces skill ceilings as well: it just doesn’t have much depth to its combat, movement, or stealth, because the systems aren’t very open-ended. The developers need players to hit a minimum threshold of cool” no matter what, so the field must be constrained.

When you play, say, Dark Souls—a videogame with superficially similar combat to Assassin’s Creed, but in truth far complex and more satisfying—you learn all the mistakes you make as you play. Same goes for Titanfall, or chess, or most other games with this freedom and depth. When you play the latest open-world action-adventure AAA map game, you learn primarily only how few mistakes are even possible. Cool moves demand the existence of uncool moves, and designers often seem eager to remove every possible uncool move.

Many crunchier systemic games fall into a related problem, which is having a single obvious move you should use every time, the optimal choice in every case. You run into this in roguelikes or certain deckbuilders: a flush deck in Balatro is a lot of fun the first few times, but it gets old quick. You can deliberately avoid flushes and still succeed, sure, but having such an obvious, easily-repeated, usually-optimal move gets stale quick.

Tabletop RPGs often run afoul of this issue. If I play a rogue, in say, Dungeons & Dragons 5e, I should try to land my bonus damage sneak attack every turn. Rogues don’t get any per-day abilities (an intriguing design choice that I support, for what it’s worth), so it’s just sneak attack, sneak attack, sneak attack. This gets old fast, and Wizards of the Coast knows it—one of the (good!) changes made in 5.5e was to, at high levels, give rogues alternative options for sneak attack: they reduce the damage total, but allow tripping attacks, blinding attacks, and so on. This helps rogues stay less bored, in theory, because now they have more to do.

You can see this philosophy pushed to its outer limits in something like Pathfinder. Pathfinder has innumerable options available to its players—ancestry, background, class, spells, pets, feats of a hundred varieties, dozens of weapon tags, and so on. More options, more choices, more cool moves, right? Surely, Pathfinder players must always feel like they’re doing more cool moves than their less-optionful compatriots at other tables, right? More, more, more?

In a word: no. This blind maximalism seems obviously wrong to me.

From my perspective, there are two basic ways to do a cool move in a tabletop RPG, and the difference hinges on Markus Montola’s third rule of roleplaying, the Character Rule. To recap, Montola describes roleplaying as following three rules: the World Rule, the Power Rule, and the Character Rule. They state, respectively:

  1. Role-playing is an interactive process of defining and re-defining the state, properties and contents of an imaginary game world.

  2. The power to define the game world is allocated to participants of the game. The participants recognize the existence of this power hierarchy.

  3. Player-participants define the game world through personified character constructs, conforming to the state, properties and contents of the game world.

In brief, roleplaying is the act of imagining a world and how it changes, together with your friends, through only the characters you play in that world. World, power, character.

If you read the histories (Playing at the World and Shared Fantasy, mainly) most of the early wargamers that played early RPGs and proto-RPGs followed these rules to a greater or lesser extent. Most tables had one or more referees in charge of the world, and players had one character they controlled; outside of their characters, players couldn’t affect the world. Classic D&D.

This is still the model for most RPG tables, and many (most?) rulebooks simply assume it to be the case. By Montola’s three rules, much of what these players do at the table is roleplaying—except for, of course, the jokes, Cheetos, rules arguments, chatting, and so on. But when they play, these players define a world, together, through their characters.

But! at many tables and according to many rulesets, you often break this third rule, the Character Rule. That is, players regularly define the world outside their characters. In Blades in the Dark, this looks like a player (rather than a character) spending Stress points to declare a flashback—that there’s a gun under the table, or that the window was left unlocked, or even that the night watchman and the gentleman’s valet are secretly in love and having an affair. That particular diegetic Blades scoundrel didn’t do anything to trigger that Stress spend: it occurs purely at the player level.

In Wanderhome, this gets pushed further, with players writing all of the world. Wanderhome players often take inspiration and suggestion from their characters, but are never confined in their ability to affect the imaginary world by what their character can do. These rulesets often lean towards a more storytelling” sort of model, at the far end of which lie collaborative writing exercises (which range from Hey, let’s dream up a new short story collection together” to something like Microscope)—and improv.

By Montola’s definitions, improv is not roleplaying because improv actors often define the world outside the limits of what their characters can do. If we’re doing a scene and I say Boy, it’s cold in here,” and you say What did you expect, living at McMurdo Research Station?” now we, as characters, are in Antarctica. By contrast, if we’re playing Mothership and I say Boy, it’s cold in here,” and you mention McMurdo, the Warden would very likely say No, actually, it’s because you’re on the deserted ice moon Galicon-9-3, inhabited by heatsucking slugs.” Improv actors define their world through dialogue, the words the actors say, but the characters themselves are not diegetically changing the world.

Collaborative writing likewise does not qualify as roleplaying for much the same reason. Authors possess tremendous ability to alter the world outside the characters they write, and do so more or less constantly.

Despite Montola’s definitions (if you can imagine), many RPG books and tables embrace these methods. Accordingly, many people who claim to be playing a tabletop roleplaying game are, in fact, doing some other activity, at least some of the time. You can imagine this as a simple little scale: Microscope defaults to being out-of-character and dips into scenes only on occasion (mostly not roleplaying), while Blades usually follows the Character Rule and only steps out of the characters for a few beats at a time, like when you spend Stress (mostly roleplaying).

At all tables, much of what constitutes a session” is not roleplaying. Those Cheetos, jokes, scheduling arguments, rules arguments, safety tool invocations, smoke breaks, and so on—all are not roleplaying. Even just when your GM asks you Hey, you’re from the Novan Empire, right? Do you think your family has land in the Western Themes?” and you say Yeah, probably, my background says I’m from Skiathos, so I think that makes sense”—in that moment, as you step outside your character to change the world, you stop roleplaying.

Thus, we return to doing a cool move. In these more collaborative, writers’ room”-style games, a cool move is rarely something that your character does. Declaring your guy in Masks to be the most awesome forcefield-invincibility-triple-multiclass badass doesn’t mean very much because someone else can just say Yeah, Dr. Deltron’s laser fries you anyway, and your armor begins to peel away, revealing your old childhood scars.” That ability to override the imaginary world via authorial fiat makes powers and features mostly useless from a goal-achievement perspective. Nearly all RPG rulesets about collaborative storytelling thus are not about solving problems in the world, and so the cool move must change.

Because the goal in these collaborative storytelling games is not To win” (slay the dragon, solve the mystery, etc.) but rather To tell an engaging and meaningful story, together,” a cool move is much more about how it contributes to the story, or the world, or whatever else you care to write about together. The cool move in Microscope might well be to say Oh, wait, what if each of the psionic cyborgs had like, an astral umbilical cord situation, and sometimes those cords got cut and the cyborgs were severed from the Hive Mind and became independent? But it was like, an existential crisis each time?”—a move that solves no problems for the characters in its redefinition (indeed, it probably only creates more), only redefines the world in an exciting way.

Does this meet our former criteria of a cool move—that is, to be unexpected and effective? Yes, I think. If your goal as a table is to tell an engaging story, dreaming up exciting and dramatic narrative elements is both unexpected and effective. If other players guess what you’re about to say, well, that’s much less cool; likewise, if it’s just kind of some long diatribe that doesn’t add anything, that too is rather less than cool. It’s easy to spot a cool move in a collaborative story because we, as humans who consume media, regularly see so many uncool stories.

But let’s consider the other route—the second way to do a cool move in an RPG. In collaborative storytelling, it’s cool to have exciting ideas. In what we might call strict” Montolan roleplaying, exciting ideas are filtered through a very specific lens: the lens of character. If my idea can’t be enacted through my character, it’s maybe fun to consider but worthless for the purpose of the question at hand. It’s fun to imagine, say, What if goblins had hot air balloons?” but that idea alone doesn’t solve the problem of your characters needing to climb a tall cliff. In these kinds of strict roleplaying games, the cool move often revolves around coming up with an exciting or clever solution to a problem within the narrow scope of what’s possible for your characters to do.

A cool move in a post-OSR game looks like, say, using the engine block from your party vehicle to run electricity through the toxic oil seeping out of the facility, thus shocking all the techno-goblins inside. Or surveiling the vice president’s wayward child for scandalous kompromat to use as leverage in gaining access to a CIA field base. Or even just jamming a pair of sabers through the handles of a door to hold off the Imperial soldiers trying to break in. Whatever. The point is, a cool move involves using the in-world resources and options available to the characters in an unexpected, powerful way. The options available to characters and the options available to the players are, for the most part, one and the same.

This brings us to the question of rules. Earlier, I mentioned state spaces, the field of possible game states within a rules system. Are these various cool moves in the rules?” On paper, no: most OSR and post-OSR rulesets are quite spare and lightweight, with only a few (if any) powers, abilities, or features available to player characters. But in practice, these moves do fall in the rules, because, well, it’s not like using a car battery to electrocute goblins is cheating. These odd sort of rules-outside-the-rules are a result of the different frames of play in an RPG. Old-school-ish play usually relies far more heavily on the rules of the diegetic frame—the rules of the imaginary world—rather than endogenous rules of the written ruleset. Car batteries, the conductivity of toxic oil, techno-goblins dying from excessive electricity: none of those exist in the endogenous written rules, but all clearly exist in the diegetic.

By emphasizing the diegetic rules over the endogenous, OSR and post-OSR play can get away with minimalism in their written endogenous rulesets, because they just don’t matter that much. (By contrast, this kind of play gets tremendous use out of detailed adventures, especially ones that do the legwork of fleshing out an imaginary world in detail.) The cool moves in a post-OSR game are about exploiting some unexpected—often only implied—element of the imaginary world to achieve a character’s goals. The open-endedness necessary for surprise comes from the near-endless breadth and depth of the simulated world, rather than the vast complexity of the written ruleset. (This is sometimes referred to as tactical infinity”, but it holds true even outside of tactics.) In these kinds of simulation-heavy games, I do a cool move by employing the features of the imaginary world in clever ways.

Okay, so, two basic kinds of RPGs, two basic kinds of cool moves. Collaborative storytelling games, where cool moves are about enhancing and building the story and world, and world-simulation games, where cool moves are about wielding the contents of that world. Very different kinds of play, very different kinds of cool moves, but we can see a path forward in each.

What about RPGs without many cool moves? I get how to do a cool move in A Land Once Magic or The Vanilla Game, what kind of games make it hard to do a cool move? There are two common answers I see: constrained rulesets and confused rulesets.

Let’s start with the latter. Imagine you’re playing an RPG that, on its face, is about problem-solving—slaying dragons, political scheming, mystery-solving, and so on. You find a secret chest hidden in a wall and crack it open, excited to see what secrets lie within. But then, the rules say something like Now you decide: what lies within the chest?” and whatever you say, it becomes true. Where we were previously all happily following the Character Rule, suddenly some rule inserts itself and asks you to break it, to step out of character.

As a player, this confuses me. If I’m trying my hardest to win using all the tools available to me—like I would in a post-OSR kind of campaign, or, you know, most other kinds of games—then I should obviously say The chest contains a +3 sword of dragonslaying!” or The chest contains signed documents proving the Vice President sold cocaine!” If we’re trying to win, I want to win. But, there’s a strong cultural tendency to avoid such blatantly favorable world-defining. It’s seen as crass, brutish, powergaming; it’s seen as exploitative, somehow.

I’m sure you’ve seen the opposite, too: you’re having fun playing out a collaborative soap opera of melodrama and big emotions, but then suddenly some rules-switch flips, and you step into grid combat. Where before making self-sabotaging decisions was part of the fun, now play becomes all about damage optimization and number-crunching, with poor tactical decisions being heavily penalized. That, too, is confusing.

When I play an RPG (or RPG-like game), I want to know upfront: is this a storytelling kind of game, or a problem-solving kind of game? The rulesets that try to blend both often feel like they pick up the worst of both worlds, demanding players switch between two very different sorts of minds or risk spoiling the whole affair. These overlapping rulesets make it very hard for me to do a cool move: I can no longer trust that my melodramatic self-sabotage won’t shaft us later, nor can I trust that my clever rope-beartrap-soap trap won’t be undone by the suddenly rules conjuring an unexpected downside, hidden cost, or heavy price” into existence. It’s confusing! Why do we keep releasing these kinds of rulesets? I can’t tell what kind of game we’re trying to play, and that makes it hard to do cool moves!

These kinds of half-storytelling RPGs are but the first kind of RPG I see that makes it hard to do a cool move. The second is what we might call the overly-constrained RPG ruleset. These are the rulesets that insist on every action falling into their written rules system—that the only state space that matters is the state space explicitly defined by the rules. If it isn’t in the endogenous rules, it isn’t allowed.

This was super common in the 90s and 00s (and still fairly popular today), where you saw ever-larger lists of skills, items, and options to try to cover every possibility of the imaginary space (an impossible task), like the endless glut of 3.5e splatbooks. These rulesets become a dictionary” of possible moves: anything outside that dictionary doesn’t exist. I don’t think its coincidental that many of these overly-constrained RPGs emphasize tactical grid combat—far easier to say this is what you can do” when space is so neatly and rigidly defined.

These constrained rulesets make it difficult to do a cool move because every option must be designed by the book’s writers. Videogames get away with this because they can do far more math in the background, running physics engines and procedural generators and so on—on paper, Diablo and D&D have similar basic rules, but the sheer quantity of math being done to keep Diablo running far outstrips anything a human could do. Things can happen in a videogame that the player doesn’t quite understand and it’s fine; in an RPG, if the players don’t understand how a class feature or spell works, the game screeches to a halt. Practically zero videogames explain the full extent of their internal mechanisms because those mechanisms are so complicated they’d just confuse players.

RPG writers can’t afford to create rules of such complexity. Without players, RPGs do nothing, so an RPG ruleset must be simple to understand. But, all this rules simplicity creates a problem: how do you do a cool moves if the state space of play is very constrained? If the designer must write out every possible move, and the players must be able to read and understand every possible move, where do we get cool moves?

The typical answer for these kinds of traditional rulesets is breadth. They bloat so quickly because in order to maintain momentum, there always need to be new options available to players. If I show up to the table with an official splatbook in hand, ready to play some harebrained new class, for a few sessions, the fact that no other player knows what my character can do makes it seem cool. It’s hard to grapple and comprehend with vast quantities of options, so even simple-but-unknown actions can maintain some of that cool factor.

Eventually, though, this breadth runs out. If feeling cool relies on research, your players will hunt down every option and combination and use it to build ever-more-optimized characters. As a game designer, you must constantly supply new options to stay ahead of the diehard fanatics—who, unfortunately, are also your main market. At the table, this kind of emphasis on character-building transforms play into essentially score-tallying: how well did you build your character? Did you maximize every value, optimize every choice? Did you spend enough time doing research? Sure, you might occasionally stumble upon a cool synergy in your build, but a cool character build does not make for a cool move in play, live, at the table together.

I see both of these—the ruleset that demands all actions stay within the predefined endogenous bounds, and the ruleset that constantly breaks the Character Rule while asking players to problem-solve—all the time. They account for the vast majority of unfun sessions I’ve played, sessions where it felt like I was either being pulled in two directions at once or else utterly locked into a grind. I want to feel cool playing an RPG, and to do that, I need clarity of purpose, and I need freedom. Without these, play loses its spark.

I described two main methods for doing cool moves in an RPG (or RPG-like game): collaboratively storytelling and redefining the world for extra creative drama, and wielding an ironclad imaginary world in clever exploits. Critically, neither a videogame nor a board game can recreate these—both are too constrained, too closed of systems. And yet, because so much of RPG design culture cribs from these other, more popular mediums, I keep seeing designers trying to imitate the closed systems, and it always fails eventually.

So, the next time I sit down to play your game, I’m going to ask you: how hard is it to do a cool move in this game?



Date
March 19, 2025