Actually, recommending that anyone follow any particular path into music is pretty shady, in my opinion. At least, if the point you're trying to make is that people should be listening for their own enjoyment, and not to become an expert in the "field." The only advice I'd feel comfortable giving (though, of course, I'm not as into or as knowledgeable of music as some others on this board or in this thread) is to pick a band or a singer that you really enjoy, and listen the hell out of them, one album after another. If you're keeping tabs on one band, you're likely to pick up on another; or you might just stumble upon something (say, something that's being talked about in one community or another). Listening to one album that gets thrown at you after another is more likely to leave you unfulfilled and dragging behind. You're not lacking in resources to make the connections between bands; check out music sites (last.fm, allmusic, various blogs), also the labels that sign the bands you like.
Aaaaand, pretty soon, you've got a shelf (or a hard drive) full of names that none of your friends have heard of. Which has its pleasures, I suppose... definitely not worth the time and effort, though, if you haven't really enjoyed what you have.