Planescape is D&D's most expansive setting - you could argue that it actually encapsulates all other D&D settings, as the whole premise of it is the traversal of the many planes of the D&D multiverse - which would include the 17 Outer Planes (including The Outlands, which are the hub of the Great Wheel,) the Astral Plane, the Elemental Planes (the four big ones and then the various hybrid planes, also, at least in 2nd Edition cosmology, including the positive and negative energy planes, which then creates hybrids with the other elemental planes) as well as the more recently codified Feywild and Shadowfell... not to mention the Prime Material Plane where most D&D takes place.
These planes can be used in more down-to-earth campaigns, of course - the influence of the planes and the gods and outsiders that inhabit them can often be a fixture of a D&D campaign set in one of the prime material worlds - if you have a campaign about some demon lord's attempt to destroy your world, you might have demons popping up for your party to fight and maybe even have some chapter of the campaign see you braving the terrors of the Abyss to cut off the assault from its source.
In such a case, the experience of traveling to one of these planes is a high-stakes, highly dangerous phase of the story that should hopefully resolve with the players escaping and returning to their home world.
Planescape, though, imagines these places as ones that persist even when there is not some crisis that has to be resolved. It imagines the planes as places where people live their whole lives, not only as an afterlife, but as a place where one might live out a natural mortal lifetime, even though one is amidst all manner of supernatural beings in a landscape that is shaped by thought and philosophy.
The 90s saw a bunch of D&D-based computer RPGs, such as Baldur's Gate, Neverwinter Nights, and, most relevant here, Planescape: Torment.
The latter reflected in many ways the philosophical underpinnings of Planescape as a setting - the story here is not about stopping some demon lord or archlich. Instead, it's about the individual protagonist, a man who awakens in a morgue covered with scars, trying to figure out who he is, within the city of Sigil, and the stakes of the story are really more about whether the Nameless One can make amends for the things he's done and ultimately change his fate.
Planescape's philosophical focus was paired with a distinctive look. Artist Tony DiTerlizzi provided all the illustrations for the 2nd Edition Planescape line - this was back when TSR was publishing a lot more books for their various settings, in contrast to the 5th Edition strategy of generally doing one product per setting other than the Forgotten Realms (though I suppose Exandria and Ravenloft have gotten two). DiTerlizzi's gorgeous, sketchy style gave the whole setting a very different feel - sure, there were demons and devils (renamed in response to the Satanic Panic as Tanar'ri and Baatezu, respectively) but they looked a lot funkier - a bit more like they were from a fairy tale or a Jim Henson movie.
Key to the setting, as well, was the city of Sigil (brief aside: old-school players insist that it has a hard "g" sound, to rhyme with "wiggle" despite the actual word sigil using a soft g. I suspect it's that a lot of people simply didn't know how that word was pronounced, and that they are claiming this as canon to cover for their mispronunciation. But perhaps we'll get official word if we get an official publication).
As a relative D&D neophyte (though I guess with 7 years under my belt, that might be less accurate a descriptor,) Sigil can seem a little odd - Planescape has all these planes to explore, but it seems like most of the source material is really focused on this one city. To be fair, it's a super cool city - Sigil floats above an infinitely tall spire that rises out of The Outlands (we're in planes of thought and concept, so that's not impossible) on the inside of a toroid (donut-shape,) such that if you're anywhere in the city, you can look up and see more city.
Sigil has a lot going on - it's ruled by the Lady of Pain, an enigmatic figure who is apparently omnipotent within the city, but if you value not being shredded in an explosion of gore, do not worship her as a god. Indeed, Sigil is a god-free zone, and the last god who tried to enter it was annihilated by the Lady, along with every last one of his worshippers.
Sigil is also home to the Factions - these are groups of philosophically like-minded individuals who help run the city but also follow their own very strict codes, and their worldviews are often quite strange.
So, already, putting this setting together for 5th Edition is a bit daunting.
Practically speaking, the way I see it is that there are two key elements of lore that we would want to cover:
First is the Planes themselves. In several earlier editions, there was a "Manual of the Planes" book - not under the Planescape title, but simply as a guide to the various outer, inner, and transitory planes.
In 5th Edition, we have a bit in the DMG that covers the planes, but most are not terribly detailed. The Nine Hells and the Abyss, the two planes most likely to be the home of your campaign villains, get a bit of explanation with descriptions of various layers - from the homes of various demon lords in the Abyss to the nine layers of the Hells and their reigning archdevils. But, for example, Carceri gets like three sentences.
I'd love to see a detailed sourcebook for 5th Edition (or, potentially 6th or whatever the 2024 releases are called) that just gives us the nitty-gritty of the planes, perhaps with a bestiary that includes native inhabitants of each of those planes - tell me, for example, how the denizens of Bytopia differ from those in Arcadia, or what makes the fiends of Carceri different from those in Pandemonium.
Then, I think, we could have a truly Planescape-focused release that would give us the modern version of all those Planescape specifics.
We've seen in the recent Unearthed Arcana, Wonders of the Multiverse, that backgrounds like Planar Philosopher could allow one to play as a member of one of Sigil's factions (I should note that these factions are not limited to Sigil - they have holdings across the planes).
2nd Edition had a lot of fiddly rules about what sort of magic worked in various places, and I don't know if that fits in with the 5th Edition design philosophies, but I'd love to touch on new races, subclasses, spells, and items that would fit within a Planescape game.
I also think expanding on the effects of the planes and how one's philosophy and alignment could affect someone traveling the planes could be interesting. Van Richten's optional rules for fear and stress might be an example of the kind of things you could play with here.
5th Edition has deemphasized alignment as a core part of your character - indeed, I have friends who come up with alternate alignments like "helpful good" or "hedonistic neutral," which are fun, but I think Planescape could make alignment pretty important, given that it's the underlying structure of the planes.
Moreover, something I'd like to see is a bit more experimentation in the aesthetic - 5th Edition has had a very consistent art style for the most part. I think it's important for Planescape to feel strange and otherworldly - all fantasy worlds are somewhat otherworldly, but I think Planescape needs to feel particularly odd. Tony DiTerlizzi's art did a great deal to establish the feel of Planescape, and I'd want it to retain that surreal, 90s "new weird" look and feel.
This extends to gameplay - I don't think Planescape needs to be totally combat-free, but I think any sourcebook should offer some guidance on how to build fun challenges that don't revolve around violence, and, more importantly, ones that will give characters of every class something to do.
One thing I loved about Van Richten's Guide to Ravenloft was that, in addition to the lore surrounding the various domains and their Darklords, there was also a section in each domain chapter that provided tools for making adventures that take place in that specific domain - like how to run a plague lockdown in Richemulot or the ways to gain renown with the warring factions of Kalakeri. Taking this approach when detailing the various planes, or the various factions, could be very useful.
Now, as someone who is 2+ years into a Ravnica campaign, naturally the notion of philosophical factions that run a giant city is a little well-worn ground for me at this point, so I'll confess I'm less interested in the Factions, but I think the way that Guildmaster's Guide to Ravnica is laid out could also be useful for structuring an exploration of Sigil.
We're still a couple weeks away from the Spelljammer box set coming out. I'm curious to see how well that works out (I'm still a little skeptical of the short lengths of the books in it - even with all three, that still only adds up to 192 pages, which is pretty short for a sourcebook). I do think that Planescape is so expansive that it might not fit within a single book. At the very least, I'd hope for a big tome like Van Richten's, but if I had my druthers, we'd get numerous releases.
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