Cities by Dwarf Fortress

Although I've stopped playing it, the development of the vast, ponderous, procedurally generated, obsessive-compulsive amazingness that is the Dwarf Fortress computer game continues to fascinate me. The two programmers have set forth a task truly worthy of a Demiurge: to represent everything in a vast and random fantasy world, down to the last severed left toenail of a naked mole rat, down to the last one-humped camel leather loincloth and prickle berry bush. What it lacks in graphics (strictly ASCII), DF makes up for in detail.

Sometimes the random generation intersects with the needs of roleplaying and coughs up something useful. I'm not so sure about typical DF names like "Udo Spoonsclasped" but this series of random city maps just cries out for Photoshopping into a campaign. Draw on a wall, some big buildings, street names and you're good to go!