I realize I may be wading into somewhat murky territory here, but I shall wade away nonetheless. ;D
The New Republic ran a fascinating article on this subject back in 2007, as it happens, within the context of postwar American politics:
http://www.newrepublic.com/article/the-musical-mystiqueI was most struck upon first reading it (a few years back, when Alex Ross linked it from his last blog) by the anecdote about George Benjamin and "the music of our time". That has stuck with me because it's the flip side of the argument we're having - yes, classical music is no longer part of the mainstream of pop culture, but at least in part that's due to some classical musicians' insular attitudes. (I feel that the academics of the 50's and 60's have a lot to answer for.) If anything gives me hope, it's that a large body of composers are turning their back on such feelings and are looking for a way to genuinely connect with the contemporary listener. Not all of them succeed, but enough do that I think we may be starting to see a way out of the wilderness.