I think that art is always an act of experimentation. Every novel written, every painting painted, every song written, recorded, and mixed, and every movie made by the staggering number of people who contribute to the project, is an attempt to see if some idea, technique, or premise works. What "working" means can be measured in different ways. I've always rejected the idea that, for example, some movies are art while others are not. Even if you're making the most hackneyed, profit-focused movie, it's still art. It can be bad art. But it's still art.
D&D is a weird proposition. In some ways it is a product - created by Wizards of the Coast and sold to us in the form of books and online services like D&D Beyond. But it's also a medium in which DMs craft worlds and stories, and in which players craft characters and collaborate in the creation of those stories.
I think that the world of art criticism has struggled to wrap their heads around games as art. To members of my generation (that would be the older side of Millennials) I think most intellectually-minded folks would consider games to obviously be a medium of art. I remember when beloved film critic - and one who in particular had a lack of pretension when it came to movies that were "low art" - Roger Ebert objected to video games being art on the grounds that the player interacted with it, thus potentially changing the form of the presented work. I think that's a roundabout and retroactive argument to be made to justify what was likely a sense of generational anxiety toward a medium that has outstripped film at least in terms of monetary intake. After all, this would also seem to deny the "art"-ness of high-minded performance art pieces that require audience participation. And I think that it's a blurrier line than perhaps Ebert thought of it - going into a museum installation, for example, you decide the pace of exploration (much like a game, frankly.) Perhaps, as someone attuned in particular to the medium of film - a medium in which the auteur (usually director) has profound control over everything the audience sees and hears - his view was shaped more by his chosen art medium than any objective position.
I have a fairly broad definition of art that I even think might be too restrictive - essentially, I think it's any object, performance, or experience that is created to evoke an emotional response. And yes, that means that advertisements and fast food and political propaganda stand under that wide umbrella. Art isn't a matter of quality or pureness of intent.
So, we come back to D&D.
I've been thinking about the challenge of being a DM. Once a week, I have a group of 4-7 friends who log into Roll20 and Discord and I guide them through my take of Ravnica as we continue an ongoing story. I have a series of nested goals: I want the campaign overall to be satisfying, with arcs and developments that make the players feel like they were part of a thrilling and, perhaps, meaningful story. I also want this session to feel memorable and substantive. And then, I want this moment, right now, to feel meaningful and worthwhile.
I think a lot - maybe all - DMs have this little mental check-in after they run a session. The glow of the excitement of running the game, and the fatigue of being the primary talker for four hours, gives way to a post-session analysis: did that work? Are the players having fun? Am I giving them enough agency? Am I giving them enough content?
I have a serious perfectionist streak. And it's not a very helpful one - more often than not it cripples my creativity, making me doubt my ideas before anything get onto the page. When I picked up the core D&D rulebooks in 2015, I set out not just to be a DM - I wanted to be a damned good DM. And when I have players tell me that they've enjoyed the games I run, it makes me feel amazing. But there's a little voice in my head that is always talking about how it could have been better.
"Sure, these monsters were cool, but couldn't you have had some environmental wrinkle to make the fight more complex?" "That session was just kind of wall-to-wall combat. Aren't you worried your players are going to get fatigued with all this battle?" Or, conversely "Oh man, we didn't roll initiative at all this session - aren't you worried your players are annoyed they didn't get to show off all their cool abilities?"
Last session was basically just one long combat encounter. I've found that tier 3 characters (especially with a pretty generous flow of magic items) have been pretty hard to challenge (well, to be fair, I think it's specifically that this party probably has an average AC of 19 or 20, so the low-level "minion" monsters barely ever hit any of them - when it's mass saving throws, things are a little scarier) so I built an encounter around saving as many people as the party could - a sudden attack by the Golgari Swarm saw infectious zombies spreading their corruption to various civilians, and so the party had to try to corral a bunch of commoners who, themselves, would become zombies if taken down by the monsters. I think they wound up saving roughly a third of them - which was honestly not that bad considering that they didn't know the mission when initiative was rolled.
It actually turned out really well - the players had fun (and some seemed to get almost as excited as I am about the way dynamic lighting shifted the gameplay - the Fighter/Paladin has a Sunblade and the Cleric cast Dawn on himself, so illumination wasn't as much of an issue as line of sight.)
But I think I also started thinking about my goals as DM and the sessions I run differently. They don't need to be these perfect, epic experiences. Instead, they're all experiments. I'm going to try something, and if it works, great. And if it fails, that's also great, because we learn more about the game and how to build it.
DMing is an art, not a science, after all.
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