Here's an NYT essay on Generation X's midlife crisis. As a cohesive generation, they could make sense of the phrase "traitor to my generation," unlike those born from 1958 to 1964 or from 1980 to about 1986 or so. And a lot of their mannerisms and styles of dress are still stuck in a 1992 media studies seminar. Still, I've been surprised by how much they are coming to realize how great the pre-1991 culture was, given how terribly they vilified it during their hey-day.
I haven't seen Hot Tub Time Machine or Greenberg, so I'll have to take the author's word for it that they paint the '80s in a charitable light, especially when the characters see how little the Millennials (born after 1987 or so) appreciate Duran Duran, chasing girls, and so on. Last year there was Adventureland, and while the actors' performances belonged more to our own meta-ironic age, the setting and the soundtrack captured the culture pretty well. The same is true for Donnie Darko. I struggle to keep up with movies, so there may be others in this vein, but that's a good number right there for such a specific kind of movie.
Although as young adults they mocked the wild culture of the '60s through the '80s, Generation X has had enough time to reflect on it and realize that it was a lot more fulfilling than masturbating about the politics of identity, cracking sarcasm, and pretending to be too cool to fuck. They're going to cherish Heathers and the better John Hughes movies more than Reality Bites or Boyz in the Hood, post-punk and college radio over alternative and indie, and -- though few will admit it consciously -- policy under Reagan (not so much Bush) over policy under Clinton.
I have noticed an exception to that general trend, though: the youngest Gen X-ers, born between about 1975 or 1976 and 1979, are more likely to stubbornly adhere to alternative or gangsta rap, third wave feminist ideas -- such as believing that chasing pussy is a waste of time or a human rights violation -- and staying inside rather than going out. That's just an impression, but it's based on very few of them joining in the above recollection of what was great about the pre-'91 culture. The rest of Generation X, born between 1965 and 1974 or '75, has vivid first-hand memories of coming of age during carefree times. They might not be able to recreate it on film these days, as we saw with Adventureland, but you can tell that those who actually lived through that zeitgeist would love to do it again.
Those in the tail-end of Generation X, however, hit puberty right as the culture wars were erupting. They may have memories of what childhood was like in an easygoing, anti-helicopter-parents environment, but they don't have any first-hand experiences of that world as adolescents or young adults. (For the same reason, these late Gen X-ers do have the best taste in video games, for whatever that's worth.) That must make it even easier to caricature the pre-'91 culture as merely the excesses of a bunch of hippies, disco dancers, and material girls. It's harder for the rest of the generation to believe that because they have plenty of counter-examples piping up from within their own minds.
But for the most part, even the pioneers of meta-irony are growing aware of how lame it is to hurl sarcastic barbs all day long in a status-seeking contest among the hip, and how much more satisfying it was when people didn't crack wise so much because they were too absorbed in living their exciting lives. That shows a good deal of maturity for the generation of allegedly perpetual slackers.