The homeless are the best to get gossip from. Sure, they won't tell you what's happening in the local government, but they will tell you better stories than anyone else. These stories, however, will often be untrue (made up things like any good story, now that I think about it). Only a crazed person doesn't want to hear a good story. So, if you want to hear a good story (with some gossip thrown in) talk to the homeless, they aren't real tough to find either, so that's good. Sometimes, you'll have to throw some change in their cup to get them to start chatting, but at heart, they are the world's talkers--the last keepers of oral tradition (at least in the US).