technomage's concept of using randomized polygonal intersections might work fairly well for making some of the more complex city layouts as pointed out in the article I posted. [size=9px](I REALLY recommend that you guys at least go over it once or twice for ideas! It's damn juicy...)[/size] Though if you were to attempt to do a more New York/Toronto(where I live and it's like that too) style layout where everything is more at a right angle, with the odd exception, you could add/simplify the method where you'd be using rectangle/square polygon segments instead for the majority and keeping the streets parallel with the edges.

If you stuck a river or a lake/large pond in there for flavour then you would probably need some exceptions to handle those gaps, but it would still sort of match up with the different style of cities.

Just an alternate spin-off to add variety to your collection of cities.