I think the best way to experience a location is to get a true sense of its unique community. I'm not super interested in tourist-y locations. The coolest places are usually the ones a pamphlet can't tell you about.

I love Starfucker, Bleachers, The Shins, Lupe Fiasco, Beirut, Fun., and Company of Thieves. My favorite movie might be Robocop. And I love a good history textbook.