Here's an old picking pockets table I appreciate

 

I came across these tables from a little while ago from the AD&D Forgotten Realms City System, and it intrigued me enough to hang on to it even though I can probably count the number of times I've used it on one hand. Supposedly, there was a longer version that had much more detail (I'm imagining a classic AD&D nested-tables-within-nested-tables type of thing), but this one seems like it would have much more value during a session. 

Tables like this one—lightweight, don't require much pre-planning, meant for the players to roll on during the game and not the GM outside of the session—are like candy for old school players. They're fun and enjoyable despite not offering much substance, but too many of them could bog your game down and potentially ruin your supper. Or not, I don't know, I just assume that you can have too many and eventually they'd slow your game down.

That being said, if your players are going to spend a significant amount of time in a city, I feel like tables like this can be as important if not more than any table or method you used to actually generate the actual city itself.

It's good to have all that foundational stuff for a city figured out, but when it comes to actually playing the game players are going to have more contact with the city through activities like pickpocketing than they would if you explain to them which district is which and why they should care. That's probably why tables for carousing and searching bodies and stuff were so popular in the OSR—it's stuff players actually like to do.

Which is why it's nice that there are so many tables like these out there on the internet, because when you have a bunch of them on hand it gives even more motivation for the players to interact with the environment, and gives you a perfect excuse to sneak in some exposition. It's like how I imagine some parents hide vegetables in their kids' meals so that they'll finally shut up about how gross cauliflower is. 

Speaking of sneaking in exposition, tables like these all but hand you an invitation to alter and bastardize them as you please.  The smudged pamphlet can be from an up-and-coming cult that's going to take over the city in a couple months if they PCs don't do anything about it, or the deck of playing cards can be marked with the symbol of the gang that runs an underground gambling ring. When I DM, I'm always looking for more diegetic ways to give my players leads and information. 

I see the value in making your own tables for these sorts of things, but there's something nice about using one someone else made. When you see someone else's table and get that raw mind-to-mind exposure, your imagination gets jumpstart on new ideas you wouldn't have had before. I see on the valuable table "99-00: small non-magical book" and I think about how small the odds are for that to be rolled and then I wonder what if books were contraband in the city. Or what if all the books were the property of someone important, like a mad wizard king, and he can secretly see and hear through his books if they ever leave his library. And now he's got a bead on you since you were unlucky enough to steal it from some other sucker. 

It gets the mind a-firing. 

Anyway, there has been a lot of controversy in the OSR over the past few years, so I decided to take a brave, noncontroversial stance and say that random tables are good.

Also, I tried to do some research to see if thieftraps were actually a real thing, but I couldn't find anything conclusive (after about a half-hour of googling). I like the idea, especially as an added risk to the pickpocketing PC, but in actual practice they seem like more trouble than their worth. I would feel sorry for the poor sap who absentmindedly reached into his pocket to grab something else, only to get his fingers caught in his own trap. How humiliating.

A room contents table salvaged from the Five Room Dungeon

If you DM a more recent edition of D&D and have looked around online for some advice on making dungeons, chances are you came across the Five Room Dungeon Method. There are a lot of places online that explain what this is, so I'm not going to elaborate it here. What you need to know is that the 5RDM is an outline for creating adventures (not just dungeons) that focuses on five key elements:

1. Entrance and guardian
2. Puzzle or role-play challenge
3. Trick or setback
4. Climax
5. Reward or twist

All of these are pretty self-explanatory, especially to anyone that's played D&D for a while. This sort of adventure-making method works better for more linear, narrative-oriented play, but it's too prescriptive, it makes too many assumptions about player decisions, and it promotes fixed outcomes, so it doesn't fit the OSR sensibility. But I'll be damned if it isn't intuitive. 

Anyway, I was playing around with it the other day to see if I could squeeze out a one-shot and I ended up having a much better idea: using the Five Room Dungeon to generate dungeons. 

And yes I know it's already a "dungeon generator" but I mean in the classic "Dungeon Room Contents" sense. 

Instead of using this:

how about this:

1-2: Guardian 

3-4: Puzzle/RP challenge 

5-6: Trick/Setback 

7: Climax 

8: Reward 

9-12: Empty  

Add treasure as you see fit, or give a 2-in-6 chance of treasure for the first 3 entries a 1-in-6 chance for  empty rooms. 

***

Here's how the table works: instead of using each entry as the 5RDM intends, think about what they represent. Guardians prevent players from continuing until they are surpassed. Tricks and setbacks tax resources and punish carelessness. Climaxes and rewards are the reasons that the players/PCs care about the dungeon. 

When you read the B/X room contents table, what you get is exactly what it says on the tin. A monster means there's a monster there. A trap is a trap. A Special is... well, you get the idea. Conversely, the 5RDM room content table proposes the purpose of each room. 

A Guardian represents some challenge that, when surpassed, opens up new parts of the dungeon. Guardians could be monsters guarding a room, but they could also be a magic door that requires a special ritual to open, a portcullis and a conspicuously trapped lever, or a flooded passage that's too deep to wade through. 

Puzzles and role play challenges encompass obstacles that aren't explicitly hostile to the characters. They can be puzzles in the traditional sense, non-hostile NPC or monster encounters, challenges that force hard decisions on the players, and obstacles that involve aspects of the characters' identities (alignment, faction affiliation, class, etc.). 

Tricks and setbacks are rather self-explanatory: traps, resource-depleting hazards (torch-extinguishing wind, spooky noises that force a morale check for hirelings), difficult terrain, etc. These rooms are where players' caution and preparedness is tested and where inattention and negligence is punished.

Climaxes in the 5RDM sense are the least fit to be in old-school dungeons, so instead consider them as rooms that contain important things related to the world outside the dungeon. Or, simply consider them as major locations of the dungeon itself. A climax room is where the dragon sleeps atop its immense hoard, or where the mystic sage the players want to consult resides, or where the fountain that can cure the duke's disease is found. Climax rooms can also be focal points of the dungeon, with dynamic elements that can be interacted with by the players. Maybe this room is the control center that can monitor other rooms of the dungeon and activate all the traps on the floor, or maybe it's the central chamber where an ancient demon imprisoned in a giant iron cage (which is perhaps why the dungeon was built up around it)... 

Rewards: you can probably guess. Aside from treasure there are some other things this entry means: Information is the most valuable resource in the game, and players love having good relationships with NPCS.

***

Why choose this room content table over another one? It invites you to design the dungeon conceptually while you're constructing it. And not "conceptually" in regard to the dungeons theme or origin, but "conceptually" from a game design perspective. Instead of having each result on contents table be its own discrete thing that you're meant to find a justification for later, the 5RDM contents table more easily works out the "flow" of the dungeon as your generating it. 

Because each entry of the 5RDM contents table is broad while still being meaningfully distinct from one another, you can easily connect the contents of different rooms together intuitively. If a guardian and a trick/setback room are right next to each other, the guardian can be an orc monitoring a corridor while the setback can be two more preparing an ambush. Or, it could be a locked door that leads to a room filled with poison gas. Classic generators don't offer this sort of flexibility.

What about this contents table might be worse than other ones? Well the biggest thing is it that needs you to make more decisions, so it's more work to use this table than the B/X or AD&D tables. And since you're relying more on your own ideas, your dungeons might get stale with repeated use. 

With all that being said, think about giving the 5RDM contents table a spin if you're tired of the old generators and want to try something new. Have fun with it.