Despite the tribalism of their respective fans, OSR games and modern storygames have a lot in common. They both arose as responses to the same problem: the bloated, railroaded, rules-heavy, metaplot-infested RPGs of the later 1990s and early 2000s, which promised such vistas of wonder through their rules and settings, but delivered such disappointing experiences in actual play. As a result, they share an emphasis on clawing back genuine agency for their players, and on ensuring that 'story' is something that gets generated live at the table, instead of being written down in advance by some frustrated novelist turned GM. But they approach this objective in different ways: and while most storygames aim to simulate fictional genres, OSR games aim to simulate fictional worlds.
For as long as D&D has existed, there have always been players who have pushed back against its world-simulating tendencies. 'A game of D&D is supposed to be like a fantasy epic, right?', they say. 'So how come my heroic paladin can get killed by a stray arrow fired by some random goblin? Isn't it awfully anti-climactic to get all the way down to the big boss and then lose because of some bad dice rolls? And why do the rules punish me for fighting fair and charging bravely into battle, even though that's exactly the kind of thing that epic fantasy heroes do all the time?' In the early days, such players either played D&D with lots of house rules and fudged dice rolls, or else wrote their own fantasy heartbreakers which did a better job of reflecting how they felt the game 'should' work. These days, many have gravitated instead to games which are built from the ground up on the premise of emulating genres rather than settings: games in which the fact that heroic protagonists will never be killed by nameless henchmen, and that epic confrontations will always ultimately save the day (although often not without cost), are actually written into the rules.
There's a lot of clever design floating around in contemporary storygames. The crude ones simply mandate that this is the way things will work; the more subtle ones provide notional freedom, but weight their rules in such a way that, over time, genre-appropriate outcomes become increasingly unavoidable. If you want a game in which a heist is more-or-less guaranteed to play out like an actual heist movie, or one in which a magical quest is almost certain to play out like a fantasy epic, or whatever, then they're great. Even the later editions of D&D work towards this to some extent by giving PCs 'death saves', 'healing surges', and so on, thus reducing the likelihood of 'undramatic' events such as major characters dying at the hands of random minions. Fans of such games sometimes express confusion as to why anyone would prefer to use systems, such as B/X D&D, which do so little to guarantee genre-appropriate story outcomes. Why not use a game which ensures that every campaign will actually resemble the kind of fantasy narratives on which D&D is notionally based?
Now, there are a bunch of potential answers to this question. The three most common ones are probably a preference for games which test the skill of the players rather than those of the characters, an interest in exploring settings as if they were just as real as the PCs rather than mere backdrops for their adventures, and a commitment to truly open and emergent play within which any attempt to determine the direction of a story in advance would be viewed as tantamount to cheating. I have a lot of sympathy for all three, but recently I've been wondering whether the 'raggedness' of OSR play - by which I mean the way that it often maps very imperfectly onto the conventions of the genres it supposedly models - might also be potentially valuable in and of itself.
A genre is, by necessity, a system of simplifications. There's only so many pages in a book, only so many minutes in a movie, so foregrounding one kind of material inevitably means leaving out others: and one of the key reasons for using the trappings of genre is to advertise to potential audiences which kinds of content are likely to get foregrounded, and which ones are likely to get left out. But the constraints of RPGs are very different: an RPG campaign can easily run for dozens or hundreds of hours, and while films and genre novels usually have to hold themselves to a very tight narrative schedule, RPGs can (and often have to) incorporate substantial ebbs and flows as people arrive, leave, get tired, get inspired, get bored of things, have new ideas, and so on. If you view the objective of RPGs as genre emulation, then you probably view all that as a problem to be managed, in the name of keeping the game on-track and in-genre: this is one reason why storygames often lend themselves to very short campaigns. But if you see the objective as world-emulation, then you can embrace them. You can take advantage of the fact that RPGs make it not just possible but easy to tell the kind of weird, rich, ragged, unconventional stories that are normally found only in the realms of self-consciously experimental fiction.
An OSR D&D game will sometimes be one in which brave heroes slay wicked monsters in dark places and retrieve fantastical treasures. But it will often also be one in which whole expeditions grind to a halt because no-one remembered to bring enough iron spikes, or where the fighter ends up spending the whole evening gambling with bored watchmen in the local pub because he's a few coins short of being able to afford a new suit of armour, or where the Dark Lord of Disaster can leap out of his tomb, trip over a rope trap left by the party, and promptly fall to his doom down a bottomless pit. I love that. It's real. It's human. It's kind of sad and kind of funny and quite a lot like real life. It's less about 'realism' in the sense of modelling physics or biology, and more about just conveying a sense that the world is strange and complicated and unpredictable and often slightly absurd. I can never really believe in Mighty Heroes Slaying Evil, but I can totally believe in a wicked high priest getting randomly crushed to death after a couple of wily villagers dropped a boat on him.
Now, maybe the limitless complexity of human life is the last thing you want to model when you sit down for an RPG session. Maybe, for you, the whole point is to create a shared fictional universe in which the genre-appropriate thing always happens at the genre-appropriate time, precisely because it almost never happens that way in reality. But what I hope I've articulated here is that it's entirely possible to view the free-flowing randomness of the average RPG session, and the 'raggedness' of the narrative outcomes generated by 'old-school' RPG systems, as a feature rather than as a bug. If I just want to experience a story about epic fantasy heroics, I can watch a film, or read a novel, or play a computer game, or even play one of those D&D board games I wrote about a couple of weeks ago. But stories in which the vivid strangeness of fantasy is used to highlight the oddness and resilience of ordinary life, rather than just to heighten yet another operatic grand narrative, are very much rarer: and for those purposes, for me at least, there's still nothing quite like OSR D&D.