Sometimes I think it's a cultural thing (or an anti-cultural one).
It does seem to be true that very few ppl are open-minded enough to listen to new stuff, let alone seek it out. The ones that do often seem to be looking for the very antithesis of music as many of us know it, cuz they're bored with the same old, while the rest seem to hang onto the cliche music to the point that it's a sickness.
I dunno the answer, myself. I always put originals in my sets & hope for the best, & it usually works. For the rest, there's little I play that's less than 20 years old. Sometimes when I do solo, all I do is originals, & that usually works, too, but I've never tried that in a band situation, due to the usual audience's apathy. I also try to do songs that other bands seem to forget about. At least that keeps things a little interesting for me.