Hmmm, on a social level, yes. I can find it difficult to relate to my peers but it's more due to a broader exposure to media on my part than seems to be the norm, rather than only having an appreciation for fairly mainstream entertainment. I really oughta try and find a group of friends I can discuss Scorsese, Tezuka and Silent Hill with. Having relatively alternative/retro tastes seems to have become a major part of my personality, and while I may not become as disillusioned with contemporary works in a different time, I'm sure I would have contrived to make myself not quite fit in by some means. I know better than to romanticise past generations so I don't see any of them as fundamentally better, and for all its problems, I wouldn't want to be without the technological and cultural state the world is currently in (for westerners, at least).
I'd love to have been of a gig-going age in the mid 80s to 90s for the Britpop (not just Oasis, I'm talking Smiths, Stone Roses, Mansun etc. here) and shoegazing scene I'm really into, and I'd get to see musicians like Jeff Buckley and bands like the early Smashing Pumpkins. But I really don't think its worth it, seeing all these kind of bands live would have been great experiences, but this generation has a lot going for it. And living through Spice Girls domination was bad enough the first time, I'd rather not do it again.
Basically, I'm content to be able to enjoy the creative output of previous generations while complaining about the current state of media.
(I really shouldn't base my temporal preferences by the amount of entertainment available)