What's "Iconic" Illustration?

Here's a character lineup for the upcoming Dungeonteller RPG release. Left to right, it's elf, paladin, warrior. These are vector files created in Illustrator. I might post a step-by-step tutorial someday but for now, just enjoy. Eventually I hope to have illustrations for both genders for each character class. Next up will be rogue, wizard, and dwarf.
I find that young players REALLY want to know what their characters look like and to see their armor and gear clearly. I've made each piece of gear very "thingy" and concrete-looking. I think that's what people might mean when they describe an illustration as "iconic" -- that each object seems to have its own life and is not subservient to the entire image.
And no one did that better than David Trampier. It's mostly about how he uses negative space and line weight. DAT was intensely aware of the negative space between the lines. If you want a technical reason why Trampier's art is more attractive than Dave Sutherland's, it's that Sutherland has a more limited sense of negative space. His lines are always doing more work to describe form than the white spaces are. In a Tramp drawing, the white space is just as active as the black space. It's anything but empty. (I should say that I think Sutherland was at least Tramp's equal in terms of imaginative power, I'm just talking about his technical ability and aesthetic sensitivity).
Tramp was also more sensitive to line weight. In the salamander illustration, the spear is given "thingy-ness" with a relatively heavy exterior line weight, pushed forward even more by the mass of the body behind it. He understands how varying line weights can accent form and describe textures. Sutherland's line weights are constant and often anemic for the descriptive work they need to perform.
And let's not forget invented patterns, like hatching and crosshatching. If you look at DAT's ilustration for Emirikol the Chaotic, you can identify at least ten invented systems of markmaking, that rigorously describe the textures of stone, a horse's coat, cloth, and so on. If you're going to apply an invented pattern to an object in a drawing, you can't be half-assed or parochial about it. Above all, that's what makes me wince when I look at Sutherland's work. His crosshatching doesn't do much to convey either form or texture, it's just a fill.
I've never been able to find a primary source or written source that describes Tramp's influences, but I'd bet he was strongly influenced by two underground comix artists of the preceding decade: Rick Griffin and Greg Irons. Both of them have the same hyper awareness of black/white and positive/negative balance in their line work. Irons ended up doing the "Dungeons and Dragons Coloring Book" which makes me wonder if Tramp recommended him to the powers that be for that project.

Here are samples of Griffin's and Iron's work. Judge for yourself! If you don't want to stop there, you can reach back to look at the poster art of Mucha and the very granddaddy of them all, Albrecht Durer.

Character Sheet: Warrior

From the upcoming iteration of Dungeonteller.

 

OD&D Character Sheet Remix: Magic-User

The challenge: design a premade character sheet for blue box D&D with a focus on attractiveness and readability.

 

[Preview] Wizard Character Sheet

Another character sheet from the upcoming version of Dungeonteller.

 

[Preview] Character Sheet

I'm chugging along with the next revision of Dungeonteller. Here's a concept for the character sheet. Notice that the size of the font for the action dice is proportional to the number of dice you have. So, "Shoot" is written bigger than "Make", in this case. Enjoy!

 

[Open Question] Best Gaming Xmas Ever?

What was your best gaming Christmas?
Mine was 1977. My haul included:

Chivalry & Sorcery, 1st Edition.

Empire of the Petal Throne Boxed Set

20 packs of Empire of the Petal Throne minis

And probably one of these suits from the Sears catalog.

 

[Preview] Isometric Tile Sets

A test of the tiles I'm going to be using for mapping dungeons in the next version of Dungeonteller.

 

[Bump] Dungeonteller Free All-Ages RPG Ruleset

In the spirit of Teach your Kids to Game week:

Still available for free download exclusively from this site:
Dungeonteller RPG complete ruleset. A fantasy RPG designed for big gamers to play with their young spawn. 
And 2-sided full color character sheets for dwarf, elf, paladin, rogue, warrior, and wizard!


Dungeonteller includes:

• Optimized character classes ready to play out of the box, that can be customized as you play!
• Niche-protected roles that make every class unique and valued.
• One-roll task resolution mechanic with very simple, count-em-up math. Playable by kids as young as age 5!
• Hit points AND dice pool tracked as a single resource.
• Bye-bye, skills, bye-bye attributes, hello ten basic actions that encompass virtually everything you do!
• Start with a few class powers and customize as you power-up!
• Huge list of monsters and character powers
• Unique pay-to-play initiative system
• Class-customized tutorial adventure included.

[Preview] Wyvern

From the upcoming book.

Easter Eggs in the 1st Edition DMG

Some hidden gems in the DMG I've been dying to share for years. Here goes:
 
Page 9: Grab a set of polyhedral dice and arrange them exactly as they appear in the illustration in the right-hand column. Add the numbers showing face up (1+4+4+6=15). Notice that the top number on the d20 is blank. Now roll the d20. If you get a 15 the first time, give 5,000 XP to the player character of your choice. "15" is also the number of the next page containing a hidden Easter egg.
Page 15: Three dictators are mentioned as having Charisma 18. If you can name them without looking at the entry, you personally gain Charisma 18 but will be stabbed, shot, and poisoned before your next birthday.
Page 21: In the Trampier illustration of kobolds fighting a dragon, the kobolds' bodies spell out "E GARY GYGAX". Start with the kobold falling off the dragon's back (his arm and legs make an "E") and read counter-clockwise.
Page 35: The cartoon captioned "Dave, get the barbarian in the corner another drink, quick!" is a thinly-disguised reference to contemporary politics. From left to right the figures are Nixon speechwriter David Gergen, recently ousted President Gerald Ford, and Snake Plissken. The hatchet in the wall represents the angry mood of the electorate after the disgrace of the Nixon administration, and the "barbarian in the corner" is Jimmy Carter. If you look at the beer stein upside down, the lines on it read "JUU", which is code for  the activist chant "Justice to You" (J2U). Snake Plissken represents the everyman, wronged by his government, now dispensing justice to politicians in disfavor.
Page 42: When generating character ability scores using a straight 3d6 roll, arrange the dice on the three magic circles and press lightly. The dice will warm slightly and will produce above average results for the next six rolls.
Page 99: A recipe for apple brown betty is inserted between two paragraphs in the Sample of Play script to see if anyone ever read it. The recipe calls for margarine in place of butter, a common substitution in midcentury American kitchens.
Page 170-173: Write down the name of each of the five monster species fought by the characters in Dave Sutherland's illustrations on these pages. The letters can be rearranged to spell "A Database Drivelling Old Monk Troll".
Page 187: In the Trampier Satyr illustration, the hairs on the right forearm (left as you look at it) clearly spell out "M. Poussin", an homage to Monsieur Nicolas Poussin, a French painter known for his emphasis on strong line and mythological subject matter.

[Preview] Griffon

[Preview] Frost Giant

Another icon from my forthcoming book.

 

[Worldbuilding Fun-Time] Mobmatic Chits

Use these chits to build a web of intrigue as the PCs infiltrate a crimelord's urban network. This chitty set includes iconic characters and locales like "The Eyewitness who Gets Killed before you talk to him, leaving Cryptic Clue" and "Crimelord's Jilted and Resentful Ex-Girlfriend." Enjoy!

 

[Icon] Chimera

From the upcoming book.

[Worldbuilding Fun-Time] DungeonMatic Chits

I haven't done a chitty set in a while. This is a tool for building a dungeon on the fly. I made it to help get myself through a dungeon I'm making up as we play. Instructions:
Cut out the chits.
Place the Entrance chit.
As the PCs explore, you furtively draw (or choose) chits to place next to the entrance chit to make your DM's map. Most of the chits are functional rather than descriptive, like "Neutral Power" and "Impassable." If you draw the "Dormant Threat" chit, for example, you can decide whether it's a crypt of animated skeletons, a sleeping dragon, or a gargoyle dozing in a niche on the wall.
Some chits may need some explaining. "Key 1" corresponds to "Lock 1" and "Key 2" corresponds "Lock 2." They don't literally have to be keys and locks but you need something at Key 1 that gives PCs access to Lock 1 and something from Key 2 to access Lock 2. It could be a magic phrase, a clue, a scroll, whatever, as long as it's functionally a key and lock problem.
 As you build your DM's map, you can describe the rooms however you like, and mark connecting passages and doors between the rooms that link the chits together.
 

[Illustration] Gargoyle

From my upcoming book.

[Icon] Water Troll (with Human for Scale)

[Icon] Cave Troll

[Icons] 4 PCs

Elf druid, elf sorceress, 2 human warriors.

[Icons] Two Rangers

[Icons] Wolf Spider and Orb Spider

More preview images from my next book.

[Icons] 4 Harpies

[Icons] 7 Goblins

[Monster Art Preview] Fire Dragon

From the next iteration of my Dungeonteller RPG:

 

Sample Monster Book Page: Ghouls!

Sample Monster Book Page: Bandits!

Another preview page from the next iteration of my Dungeonteller RPG. This time: bandits!

Sample Monster Book Page: Orcs!

OK, so you know that my kid-friendly RPG, Dungeonteller, is available as a free PDF download, right? But I'm not done. The next version will have full color illustrations throughout, including the monsters, of course. Here's a sample of how the layout is shaping up. Enjoy!
 

[Actual Play] Gaming Season Opener

Rainy autumn afternoons in New England are made for dungeon crawling. My prime gaming season runs from October til April, when the thaw comes and the bass start biting again.

Today I ran a Dungeonteller game for two moms and their seven-year-olds, session two of (I hope) a continuing campaign. I used the Mad-lib style dungeon template I created on the blog a while back. The PCs have still barely penetrated the place, starting at the upper left. Today they fell into a pit trap, rescued a rogue from the pit, and used the rogue's lockpicking skills to enter the orc lair. The two surviving orcs were in the process of making off with their companion's loot. One was put to sleep, the other sent running (although he kept showing up in various funny vignettes as the PCs continued to explore -- eating a stale sandwich they had left behind, falling into the pit trap, and so on). We ended at the giant spiders' lair, center left. Fun times.

Fresh-baked snickerdoodles, hot coffee, and tea helped fortify us for the duration! We played for over two hours, which is a long time for a seven-year-old to keep focused.
 

Live from the Dungeon

Always bring your iPhone to the dungeon.

Generic Terrain is Lazy

Challenge: design a world that has no generic terrain whatsoever. No deserts, no forests, no swamps per se.

Sure, you can start with "desert" or "forest" as a descriptor, but run through some questions to inspire you to make each region unique.

Is there an unusual form of precipitation? Does it rain dust, or ashes, or weak acid, or salt water?

What are the agents of erosion?  flash floods, giant vermin, ghosts, an everburning wildfire, warring giants, earth elementals?

How do you find water? Lick it off of fuzzy plants that capture fog? Look inside the cistern-like interior of giant conifers? Collect it from boiling springs? Place a water bottle beneath the ever-weeping eyes of the stone statues that dot the landscape?

What are the largest natural landforms and structures here? Basalt columns? Sinkholes? Petrified trees? Skeletal corpses of dead angels? Rafts of vegetation floating on a foul, muddy sea?

What adaptations have local humanoids made to survive here? Do they live underground? In tree canopies? Do they drift along beneath clusters of air-dwelling puffer fish? Do they spend their days as animals and shift into human forms at night?

Where does the past still intrude on the landscape? Colossal statues carved from sandstone mesas? Mysterious straight-as-an-arrow roads made of quartz? Piles of charred skulls? Abandoned fortresses whose walls are carved with protective magic spells? Thousands of crudely made statuettes half-buried in the earth, each with an iron pin through its heart?

What are the ubiquitous nuisances? Occasional sounds of disembodied laughter? Dust golems spun from residual magic? Storks that collect shiny objects? Innocuous mummies that only want to recite the laws of the land to any strangers who happen by?

Who are the low-level humanoids here? Bandits who ride on vultures? Hermits who live inside sanctuaries made of living vermin? Hunters who can kill their prey with song?

What are the unique resources? Geodes that contain magic spells? Parasitic crystals that grow on the skins and hides of local herd animals? Trees that can be shaped by thought?

Hope this kickstarts your sense of wonder. 



 

Descriptors for City Design

Designing a city and need inspiration? 

Here are a list of templates you can put on individual neighborhoods/districts within a larger city to stimulate your own sense of wonder:

Neglected: No one picks up the trash here. Public amenities like wells/fountains, bridges, and streets are broken or crumbling. Communal spaces like plazas and markets show no signs of civic pride -- they are unwelcoming, dirty, and shabby. The city authorities seem to have withdrawn their support for this place. The residents seemed resigned to their fate.

Barricaded: The residents of this district have walled themselves in to keep the rest of the city out. Entry is closely controlled through one or two checkpoints, or perhaps through secret passages between buildings or underground.
 
Abandoned: No one lives here anymore, despite no obvious signs of strife or natural disaster. Weeds and saplings grow up through the pavement. Houses are still furnished -- little or no looting is evident. There may be signs that people left in a hurry.

Clannish: This quadrant of the city is occupied by a single group, sharing either blood ties, ethnicity, religion, or some other common cause. Strangers are subject to curious stares at best, outright hostility at worst.
 
Lawless: This is where even the city guards won't go after dark. It's mob rule here, with small gangs of residents pitted against one another with no single boss to keep order.

Besieged: The opposite of a barricaded neighborhood. Here it's the city authorities who are trying to keep the residents from getting out. Again, it might be walled or gated, with limited legal access, but plenty of smuggling going on.

Looted: Someone swept through this district and stole everything of value. If there are any residents left, they are picking up the pieces and husbanding their meager belongings as best they can.

Razed: Once it was a bustling neighborhood. Now it's just vacant lots and mounds of rubble. Someone -- the city authorities? -- deliberately knocked down every standing structure here, and no one has rebuilt.

Flooded: It's a DIY Venice in this neighborhood. The area is permanently inundated by water, leaving residents to build higher, or adopt a floating lifestyle, with houseboats and rafts.

Burned: A fire has ravaged this district, leaving charred houses, ash heaps, and debris.

Exclusive: This district is reserved for an elite class of citizens, and no one else can enter except their servants and other invited guests. Entry is through one or two guarded gates only.

 
 
 

Watching the GenCon D&D Keynote Speech

I know, I'm a bit behind, but I just watched it. Ed Greenwood is fascinating. I could listen to that guy all day.  I even made an icon of him.

John and Mike spoke with passion about the game. And Kevin admirably kept them on track -- it's hard to DM a bunch of DMs, as anyone who's been to one of Kevin's Boston game days knows, har har. Mike spoke frankly about the philosophical flaws of 4e, regardless of how well designed it was -- how it dictated a particular play style and turned a lot of players off as a result. I'm pretty sure he was talking directly to me -- secret signals were passed. His big talking point was player input and player choice. John showed some very purty pictures. Ed unleashed a kraken-sized load of FR novels from R. A. Salvatore and others. I don't read D&D novels, but I'm glad they are there to create a revenue stream and fire up the game-lust of the faithful.

You know, back in this post, I made some predictions about 5e, so let's see how I did. Here are my predictions from January of this year:

• Overall Design Philosophy: Modular, rather than exception-based. Lots of watertight compartments you can screw with and not sink the whole ship. Emphasis will be on imagination, open-ended, interpretive play, less on mechanics. 
• Armor Class: They will use the high = good, low = bad AC scale of 3e and 4e.
• Saving Throws: Will follow the 4e model of being treated as additional forms of defense/armor, but will inexplicably be called saving throws anyway because the retro aspects of 5e will mostly be superficial nods to earlier game elements.
• Generating Ability Scores: multiple methods will be described, from strict roll-in-order to point build. The preferred method will be roll 4d6, discard low die, arrange as desired.
• Ability Scores' Effect on Play: More robust than in 1e, with anything above an 11 providing at least some benefit, but the list of bennies will be short. Strength will add damage, Con will add HP, Dex will add AC and missile accuracy, Int and Wis will affect arcane and divine spellcasting, and Cha will affect NPC interactions.
• Classes: The basic game will include only wizard, fighter, cleric, and thief (yes, thief, not rogue, another easy cookie to toss at the retro crowd). Bards, barbarians, druids, and rangers will be add-ons. Weirdly, class abilities will get fairly modular again, with separate mechanics for turning undead, picking locks, and so on.
• Races: The classic elf, dwarf, human, half-elf, and halfling. Half-orcs and gnomes will be optional. Dragonborn, eladrin, and tiefling will not be standard issue. Races will get some ability score tweaks and a paragraph or two of fluff in the basic game and that's about it.
• Skills: the skill challenges of 4e will be quietly throttled with a silken cord and replaced with a short list of proficiencies, carefully limited to those most likely to be used in an adventure. "Roleplay it out" will be the preferred problem-solving method.
• Combat: Far fewer conditions. Marked and blooded will be part of a tactical add-on. Daily and encounter powers will go bye-bye. Ditto healing surges. Combats will be shorter and deadlier for PCs.
• Spells: Out-of-combat spells will come back in a big way. Rituals go bye-bye. Several game-busting spells like scry, fly, and whatever will disappear or become far rarer.
• Magic Items: Won't be gimmes -- you'll find them in the course of play. Look for a general powering down of magic items. A +2 sword will be pretty cherry.

So how'd I do?


 

[Free Icons] 8 Bandits

Also suitable for footpads, thieves, robbers, rogues, thugs, and ne'er-do-wells.

[Free Icon] Manticore

[Free Icons] 4 Ghouls

Sadly, D&D is going to be Just Fine

After getting my secret decoder ring in the mail and huddling around the wireless set by the light of a single bare bulb, pencil and paper in my trembling hands, I've been able to obtain the latest DNDNext playtest documents. And then translate them into English in my head. 

Character creation is what I most wanted to see, especially race, class, and feat-thingie options. The new advantage/disadvantage mechanic has been used in clever and sensible ways, and really worked into the meat of the game. (Orcs can gain disadvantage in exchange for doing more damage, for example). The rules model cool things that a hero would do in a story, rather than describing how your little quasi-chess-piece can hop around the grid in slightly different ways and then slap a bitchin' name on it like Gold Gryphon Feint.

The whole "background and specialty" thing is presented as optional, but if you don't use it you'd have to make up your own procedure for doling out skills and feats. The various backgrounds (think "skill packages") are class-neutral, which got me thinking about cleric bounty hunters and wizard thugs and how unexpected pairings of class and background would make for interesting characters. The specialties (which are feat-trees, really) are as free-floating as you could reasonably make them. Acolyte thief, anyone? If you're creative, you can use the specialties to make the base classes into pseudo-prestige classes. Want a swordmage? Fighter + magic-user specialty. Ninja? Fighter + lurker. Mocha? Coffee + chocolate.

So ok D&D, you did it. You're going to be fine.  Now I can manufacture another reason to worry, namely: will these be core books I'd enjoy reading even if I never play the game? That hinges on entertaining writing, great illustrations, and inspiring concepts. I never bought the 4e books because they seemed like an issue of Newsweek for Kids. Lots of white space, enclosing bland writing with all the sharp edges wrapped in foam. Here's my suggestion. Get a different person to write each chapter and put their mark on it. Mike Mearls is going to tell you how to run combats, and when you read that chapter, it's Mike talking to you. In the DMG there would be, like, three legendary DMs or module designers writing about worldbuilding. Gosh that would be exciting. We could deal with it, really. You've done bland and it didn't get you any new converts. Go personal. If D&DNext turns out to be just fine, cool, but you've got the chance to make it special if you keep your eye on making magic and connecting with the reader.

[Free Icons] 8 Skeletons

More little icons for your personal use.

 

DNDNext English Translation Service

Yes, WOTC, I know it's just a playtest document. But does the writing have to be this awkward? I had to read it about three times before I could begin to follow it.

In the original:

"When you are in an area of civilization, you can find and take on bounties, allowing you to legally hunt down and capture or kill the subjects of those bounties. Additionally, as a legally recognized bounty hunter, sometimes the authorities will come to you with bounty hunting needs.
When you attempt to locate the subject of your bounty, if you fail to locate that quarry yourself, you always know where to go and from whom to obtain information on that quarry’s whereabouts. Usually this comes in the form of contacts you have cultivated on past hunts."

And now in English:


"You have the right to hunt down and catch or kill people with a bounty on their heads. You can find a list of bounties in any area that offers them. The authorities may offer you more work as a bounty hunter. If your quarry gets away, you can use your network of contacts to find out where the person is hiding."

A good editor could make the rules so much easier to understand. Please hire one. She doesn't have to know anything about gaming, just about writing with clarity and concision.

10 Dwarves

More little icons. Don't repost without attribution, blah blah blah.

12 Orcs

Suitable as paper miniatures and as icons for virtual tabletop games. Not for commercial use. Please do not repost this image without a linkback to my site.

DMing for 80

As a quaint form of communication, play-by-mail has joined the company of heliographs and messenger pigeons, but in the 70s and 80s, PBM games were a viable sphere of gaming activity. Some game magazines, like Steve Jackson's Fantasy Gamer, published monthly updates for popular PBM games, like Angrelmar. 

It is 1984, you pick up the magazine and read:

Again the churchmen met on the Isle of Ara to solemnize the union of the four churches into the Imperial Church. Hildric of Dragona became primate of Angrelmar and head of the Council. He appointed Divor of Hatra to be Cardinal Bishop of the Imperial Church in Angrelmar. Many secular lords attended this council, including the regent, Rathal and Prince Vicor. Vicor used this occasion to denounce his cousin, Auerlus, for oathbreaking which Vicor believed cleared his own name at the same time. The council also accepted Lady Callizar's realm into the Empire as the Principality of Shalamar. That fall, at the Feast of Alfons, the lords of the South offered a crown to their Lady Callizar.

It goes on. And those were just the most significant events of a single turn in the game. At that point, Angrelmar had 80 players, each one a lord or lady with a fiefdom somewhere in a vast continent. The guy who ran the game, R., was in my wargaming group, and I played in the campaign for a bit. He received dozens of letters each month from players detailing how they were spending their incomes, where their armies were marching, and what alliances they had formed. Everything was plotted on the big map of Angrelmar, and each player received a letter from R. detailing the results of that turn's move, which represented one year of game time. And there was plenty of player-to-player communication too, via mail and phone calls. Schemes, deals, assassination atttempts...

It all added up to an insanely detailed living world of politics, economies, and war. It was so big that no one player could possibly grasp it all. You focused on your corner of the realm, your immediate neighbors, just like a real feudal lord must have done. Because a decade would pass by in a year of real time, your character would age, marry, have kids. The resulting narrative read like something out of A Game of Thrones.

Once a year or so, R. would host a council of the realm in which players would show up at a gaming con or at his rambling backwoods house to RP in person. Any big battles between players would be played out turn by turn, using lovingly painted armies of 25mm miniatures. The alcohol-fueled scheming and backstabbing would go on all weekend. Good times.

When email came in, these games continued for a while. Despite being easier to adjudicate with the help of Excel spreadsheets and instant communication, they yielded gradually to computer gaming, and have been all but forgotten. Even the laziest googler can find some that are still going, I suppose.

R. didn't do this for free, mind you. Each turn cost $3, which was fair compensation considering that running Angrelmar must have been a full time job. A monthly subscription to WoW is what, $12 now? So tell me, how much would you pay per month to play in something like Angrelmar? If I Kickstarted it, would there be takers?

To Be Continued...

The blog will be quiet next week, but I'll be back! In the meantime, enjoy these icons I made:

 

Unpacking Task Resolution Systems

Here's a tool you can use to tease out the mechanics of any RPG's task resolution/action system. It's based on attribution theory, which in layman's terms is the study of the factors that contribute to achievement. Google it if you're interested. Anyway, this is a simple matrix that defines each factor in a task resolution system as internal or external, constant or variable. Ability is constant. It's represented in most games as your skill level or ability score or ability modifier. Task difficulty is almost always set by the DM as the standard you need to reach in order to succeed. Effort usually appears only in systems that use dice pools or spell points or any other rule that allows the PC to buy advantage at the cost of some other finite resource. Luck is whatever the die roll adds to the PC's attempt. The first matrix is blank, for you to copy and print for your personal use. The second matrix I have filled in to give you an example. It's a way of standardizing how you look at game mechanics, whether you're designing your own or making a comparative study of other RPGs. Enjoy!

Chitty Realm Sample Map

I made this tonight from the chitty realm tool. Note that you don't have to line the chits up in neat rows -- you can be a little more organic in placing them.

 

Kha's Post-Apocalyptic Chitty Realm

Kha sent me a link to a me-inspired set of chits he made for a post-apocalypse world. It's here on his blog. Cuidado! Hombres cucaracha! Love it!

Chitty Realm Worldbuilding Tool

Like Chitty City, but scaled to the size of a large fantasy realm. Cut, arrange, paste, doodle, or just read each chit and steal any idea that appeals to you.

 

Chitty City Map

Here's a map I made using the Chitty City tool I posted the other day. 

I drew the chits randomly, but placed them deliberately so that they made some sense in relation to one another. I'm looking at this map now as a PC would, wondering why there's a colossal unfinished statue on the prison island. Are the prisoners forced to labor on a huge statue of the city ruler, or perhaps of a god that will come to life when the statue is complete? Maybe the colossus IS the prison, like some huge Wicker Man full of criminals. And why is the city center an abandoned killing field? Is it accursed? Plagued by undead? Whose tower is that? Zenopus? Maybe it's Porttown from the Holmes sample dungeon!
Once I'd placed all the chits I wanted, I took a Sharpie marker and drew a shoreline and a few rudimentary geographical features -- no artistic ability needed for this sort of exercise.
I could add as much detail as I wanted from this point: bridges, plazas, city walls, entrances to the inevitable underworld beneath the city. And plenty of space to make notes directly on the map in each section. If you try one on your own, make sure you send me a link!