This topic is for naming cities that are not like other cities because something bizarre has happened with them in your campaign.
For me there are two cities, Imladris and Ost-in-Edhil.
I am trying to win the game before turn 300 ( My first game ). The large situation is that I, as Mordor, have the High Elves, Eriador, and the Dwarves surrounded in the Northwest part of the map and am trying to squeeze them like a boa constrictor until they pop like zits. I came across the mountains to Imladris and found it defended with a full stack and a 10-star general with Nightfighter. Rather than duke it out I wanted him to suffer, so I seiged with my two and a half stacks. Ten turns later, dressed in rags, he sallied. It was a terrible fight and he was the very last High Elf to die, and in his underwear. Finally! A city to bolster my finances and for me to impose the Dark Lord's regards on, as I was surviving on a paltry 3k per turn. So I looted ( not exterminated ) Imladris, and lo... my coffers exploded from a gain of 60k gold. I have never, ever gotten so much from one city. This allowed me to build more markets and buy another city from Harad for 30k. What, is Imladris the Switzerland of Third Age?
Still squeezing, there is Eriador to deal with. This guy, Matt the Malevolent, has been holed up with a full stack inside Ost-in-Edhil mocking me. He has ten stars and the Nightfighter trait, and more stacks just outside milling about. I have been outside for a decade now, trying to whittle down any straggling armies, but he just sends for more stacks to come to Ost-in-Edhil and hang out knowing that I don't have the numbers to attack the city or even get near. What are they hiding in there that the whole of Eriador protects this area? Eriador secrets? A stargate? Hot Eriador nymphomaniac women? It will be a long time before I can gather the strength to try busting into this hole. And Matt the Malevolent will have plenty of time to write books before the showdown that will likely crash the game from sheer numbers.
That's it for me. What cities have given you such outstanding situations or reasons to remember them?