I think that's what we're trying to define here...
I dunno, I've been reading back on what some people have said, and reading up on the different generations on Wikipedia (worth checking out, BTW), and some new ideas have struck me. I've been noticing that the defining birth-dates for GenYs are still a bit too broad, and that they are still v. connected with the iGeneration (which now I'm beginning to realize is a completely different generation).
Somebody mentioned The Matrix up there, and now I realize it really is a defining generational movie, even though that isn't it's main theme. For me, it seems that those who were in their teens or 20s when it was released (or at least 'aware' of it) could prolly be defined as GenY, the rest - prolly born post-fall-of-Berlin-Wall - would be considered iGen. These GenYs are prolly the same who got the end of grunge and danced to Spice Girls at one point. Which puts me in the transitoin period (b. 1988 - as if I don't have enough of an identity crisis) - although I've always identified more with the older generations, who don't seem to be quite as shallow as the no-life-without-internet, OC-watching, Paris Hilton iGeneration. Then again, I might be generalising too much.
On the other hand, I have never identified much with my sister (older GenYer, b. 1980), but then, she's prolly not the best example of a GenYer. But for the most of her folks, I still say Garden State is the closest, with perhaps American Pie defining the high school years.
As for other defining movies, Thirteen is prolly a good example of the born-in-the-late-80s generation (so late GenY, you could say), although it does kind of gloss over the technology-loving side of us. But then, I don't think we were quite that into technology when it was thought up. (And I still insist on Igby Goes Down, which at least expresses my current feelings perfectly - and I'm not trying to play the "I'm a lost generation" pose here.)
As for the iGeneration, I think they're/we're still too young to be defined by a quintessential film. Hopefully, the iGens won't grow up to be as shallow as we seem to be, and grow out of the Paris Hilton-idolizing. But the internet will still play a defining role in whatever we do, I'm sure.
Okay, I've babbled on far too much...
...nitwit...oddment...blubber...tweak...
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