"The really depressing places were always smaller towns, but those probably don't count, so i am gonna say Athens. Endless concrete, an ungodly amount of traffic, lack of public space, crawling public transport, excessively drab architecture, poverty.I think its also a lively city with a lot going on, so it never felt too depressing and i had a decent time there, but the aggressive unpleasantness of the whole place really got to me after a while."