Great post idea! My list is based mostly on nostalgia for a certain period of time in my life:
Fog (again) - Live - Radiohead
Pyramid Song - Radiohead
Fake Empire - The National
Hurt - Johnny Cash
Headlong - The Frames
Scattered Black and Whites - Elbow
Grace Under Pressure - Elbow
Starálfur - Sigur Rós
Hoppípolla - Sigur Rós
October - U2
Nah, I’d be like, go on! Do you associate that song with a particular event, person, time or place in your life? When did you first hear it? In what context is it your fave? Have you ever heard it played live? What was that like? Could you ever imagine another song taking its place or is it too sentimental or ingrained into your very being?
Basically a question like “fave colour/song” is often a simple test. The kind of answer you give should indicate whether or not the topic can be opened up or expanded upon or even just indicate if you want to talk to this person at all right now. If you answer “blue I guess”, and look completely disinterested or “insert massive pop hit of the moment” and leave it at that, then they know to go about their day or try another topic like “So what about that sportsball game/weather/current event?”. But you might give them a nuanced answer that will lead to more conversation.
It is handy to have a simple, 1 dimensional responce if you want to shut down the conversation quickly or direct it to another topic.