Iarmid, owner and proprietor of The Other Place, is a fantastic NPC for introducing new players to the Planescape setting. Throw them into Baator in the To Baator and Back adventure from Well of Worlds, then have Kylie or another tout bring them to The Other Place when they stumble into the Great Bazaar covered head-to-toe in dust and dried blood. From there, Iarmid and his assistants can answer all their questions about the planes they stumbled into and this strange city they find themselves stranded in.
Kylie the Tout is featured in Uncaged: Faces of Sigil, as well as Doors to the Unknown and some other Planescape adventures. I’ve used her extensively in my own games as an easy way to indicate to players when a message/invitation/etc. is really important: if the message is delivered by some no-name tout or factioneer, sure they’ll read it but they may save it for later. If whomever sent the message went to the trouble and expense of having Kylie deliver it, they’d better believe it’s important!
In the Abyss was the second full adventure published for Planescape, and firmly established the Doomguard faction as one of the bad guys. While the Sinkers were a part of The Eternal Boundary, they were as much a victim of circumstances as all of the other factions involved. In the Abyss put the Doomguard’s alliance with the tanar’ri front-and-centre in the form of the Ship of Chaos. It also for the first time put the player characters square in the middle of the eternal conflict between the tanar’ri and the baatezu, and forced them to make a major choice: honour their contract with the baatezu to turn the Ship of Chaos over to them, or disable the ship to keep it out of all fiendish hands. Of course, if they’re not quick enough, they might end up lucky to escape with their lives!
Updated 31 May 2015: Added The Fourth Door: A Reality Beyond
Yet another adventure anthology, Doors to the Unknown involves the players in the politics of Sigil more than most other adventures. There’s a nice strong link between each chapter as well as a rough timeline that allows the GM to put other adventures in between each chapter. There are some weaknesses in the adventure (for example, there’s no indication that the players need to take the Rod of Mercury from the gearwork golem in the Thuldanin junkyard) but they’re nothing a good GM can’t work around.
A Pathfinder Planescape update of Saure from Uncaged: Faces of Sigil.
Omott, the naïve linqua from Uncaged: Faces of Sigil, updated for Pathfinder Planescape.
Updated 9 Jun 2015: Added Chapter VII: Recruiters
The first of several adventure anthologies published for Planescape, Well of Worlds is a collection of nine short, un-releated adventures of varying quality. Some of the adventures set the seeds for later encounters and adventures, and the seventh adventure “Recruiters” includes a brief call-back to Green Marvent and the Illuminated from The Eternal Boundary.
The first Planescape adventure, The Eternal Boundary help set the tone for the later adventures and the setting in general. There are a few inconsistencies and some rough patches (many players have difficulty jumping from investigating deaths in the Hive to sneaking into the Mortuary) but overall it’s a good start to any Planescape campaign.
Addle-pated, cook at the Cold Bowl soup kitchen, and Factol Lhar.