I'm a firm believer that cities adopt personalities over time. For example, Chicago got the nickname "Windy City" in the 1890s from New York journalists at the Chicago World's Fair -- because of its vigorous boosterism, not because of strong lake breezes. I think Chicago still has a healthy ego bent on self-promotion.
My take on cities and their personalities:
Inferiority Complex (we don't have this, we don't have that..)
Superiority Complex (everyone should be like us!)
Emerging Young Lions (we wanna be big, too!)
We're Different (and we like being that way)
Can you think of other cities and their respective personalities?