Cities are an expression of the people who inhabit them and the rules that govern them. They are also an expression of the technologies we use, and our social contracts. According to Plato, they are a reflection of ourselves. There is no doubt that innovations are present in every section of the urban domain, and some distinguish themselves for their particular support of quality of life, justice and democracy. The expression of these developments can be taken as reflection of where we are on our evolutionary learning curve. So what does our best and worst work in the urban domain, and what does it say about where we are on that curve?