I'm A Banana
Potassium-Rich
IIRC you are an advocate for classes customized to the campaign / campaign setting, right? So your perspective entirely makes sense. At the same time it assumes you have a group of players who are:
(A) Willing to invest minimal of energy to grasp the feel of the setting before play (for Planescape it is cynical worldliness), and able to incorporate that into their character creation and roleplaying.
Yeah, and there's sort of two aspects of this. First, I don't think this needs to be especially hard -- just as the playtest characters have traits/flaws/bonds/racial info/backgrounds/etc. that link them specifically to FR, the same can exist for PS. If a player is wiling to invest some minimal energy in grasping what an Acolyte of Oghma or a Sun Elf is, then they should be able to invest some minimal energy in grasping what a Godsman or a Bariaur is. The carrot extended to encourage this is that it plays into your character abilities -- the cool things your character can do key into the race and faction. In the example, if you grab Second Wind from the Fated, this ties you into the setting explicitly: someone taught you how to do this, because it reflects a belief that they share with your character. But even backgrounds are part of this.
The second aspect is that players who aren't willing to invest any real energy in incorporating a different setting into their character aren't necessarily a great fit for a different setting. The presumption for a group sitting down to play Planescape (or any other setting) has to be "You WANT to try this." If they don't want to try it, that's fine, but there's no way any set of setting rules is going to sell an experience you don't want, and by trying to be "everything to everyone," it just waters down the setting. It doesn't matter how delicious that bacon is, a vegetarian just ain't really interested. And tofu bacon is not the same thing, we can all agree.
(B) Interested in going outside classic fantasy tropes of "drunk dwarf" or "kleptomaniac halfling thief." The classics are classic for a reason, even if not particularly imaginative.
Yeah, I don't have a major problem with saying that people who are only interested in the classic fantasy tropes probably won't be interested in Planescape. PS isn't about those classic fantasy tropes, at least not without tweaking and mutating and examining them, just like how Dark Sun isn't about happy farming peasants and Ravenloft isn't about saving the day.
PS has its own tropes, of course -- the outcast Tiefling with a chip on her shoulder, the freedom-loving Bariaur, the adventuresome Sensate, the scholarly Guvner, etc. It has its own style and atmosphere that can drive character hooks. They serve the same function of shunting various personality traits into your RP directly. But like I pointed out above, someone who only wants generic fantasy probably isn't someone who is going to groove on Planescape, and there's no point in making a watered-down substitute to appeal to them. It's OK -- not everyone HAS to groove on PS. But I wouldn't want a PS that felt like it had to cater to people who weren't really interested in it anyway.
It might sound like I'm being hard on players, but the fact of the matter is there are DMs who just don't understand Planescape either. I think the difference in our perspectives might be you see Planescape as another setting just like Ravenloft or Dark Sun, whereas I see it as something radically different in that it can bridge multiple worlds. Even in the original box there were options for getting a party of prime PCs to the planes and, in Planewalkers Handbook, for running mixed prime/planar campaign.
I don't think bridging worlds is all that unique, though. You can smash Eberron into the Forgotten Realms (as D&D has done), or let a thri-kreen pop up in Ravenloft or whatever if you want. You don't need PS for that, just a DM who wants to make a bit of a mess.

The thing that PS does that is unique and special is its setting-specific stuff, the stuff that it doesn't share with any other world, the stuff that lets a thri-kreen and a warforged pop up and both be defined by something more than their home settings. It gives a context for that world-smashing that is bigger than the sum of two parts.
Characters from other worlds have a place in PS, but their role as Planescape characters should trump their role in their original world. What faction does the thri-kreen join? What does the warforged believe about free will? Does a Tinker Gnome on Mechanus defy its ordered nature? And these characters should still be rarer than the planar characters. Just like running a campaign of all fighters omits a lot of diversity in the game, running a PS campaign made up entirely of prime characters ignores a lot of what makes the game interesting.
We both agree that Planescape (much like other settings) needs to be experienced thru play; actually I would say especially Planescape! Because of its strangeness. Even players who come in with well conceived PCs still are finding their character's identity/voice/beliefs during those first few levels. Does it really matter if they're prime, planar, or even excepional petitioners? For me Planescape's themes are found in the adventures which I would argue are where emphasis should be placed. Personally "Umbra" (Dungeon 55) is one of the best PS adventures written and I could see that largely working for any sort of PCs.
The moment you're asking the drunken dwarf to define their beliefs and question their assumptions, you're turning them into a PS character -- a planar adventurer. That drunken dwarf is going to belong to a faction (maybe the Sensates?) and is going to know some good pubs in Sigil, and is going to know what they say about the Lady of Pain and is going to know why he's won't be happy in dwarven paradise where there are rivers of ale better than the finest dwarven ale and is going to not be that impressed with the bacchae.
Might as well plug that into the character creation so I don't have to go through the ritual of running some "You fell down a well and wound up in the Oceanus, guys!" excuse-to-actually-play-PLANESCAPE quest.
Btw I enjoyed your thoughts on interpreting Second Wind thru the faction lens!
Thanks! I think that's the kind of thing that makes it easy to pick up the new tropes and archetypes present in PS (and is likely applicable to many settings). If every proficiency your character has or ability your character possesses comes from *somewhere* in the setting (as opposed to just happening spontaneously within a character who simply gains a level), it forms a pretty tight connection between that ability and what setting elements relate to that ability.
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