i play a lot of poker and sit and converse with a lot of random people for hours at a time ... here's a couple of observations:
(1) invariably some middle-aged guy will strike up a conversation about music as a result of some band t-shirt i have on, ask condescendingly if i listen to any older bands "like the beatles or zeppelin", and get completely embarrassed when i start talking to him politely about 60s and 70s music ... i've yet to actually meet a middle-aged guy who knows anything about music from "his era" (beyond the big hits) even though they invariably ask why "kids these days" don't listen to the "good stuff"
(2) people in their 40s to 50s talking about music (especially pseudo-intellectual lefties) ALWAYS bring up Bono and mention him as someone who their kids know, but they never have really heard of ... invariably, these are the same self-righteous "music fans" as (1) ... i point out to these people that Bono/U2 were more musically relevant not just to this generation of music fans, but about 20-30 years ago, which would have been right in their musical wheelhouse ... this implies, of course, that they really know nothing about music from "their own era" and generally leads to embarrassing silence
(3) wearing a "your favorite band sucks" t-shirt to a poker game is a great way to start a conversation
(4) super hard-core metallica fans (there's a lot in atlantic city) are really fun to talk with