I wanted to like this, I really did, but in the end I just couldn’t. There were lots of funny little bits here and there, but the sum total was just too glib, too shallow, too purposefully contrarian, and above all, too universalist and unqualified. The main problem is that he’s trying to universalize what amounts to a very narrow-bore pop culture experience. I’m only a few years younger, but very few of the touchstones(the Real World, Billy Joel, Saved by the Bell, etc) that he mentions have had any appreciable effect on my life or that of my peers. I’ve heard of them all and been exposed to them enough to have a good familiarity, but I can’t hang any of the shared meaning on them that he does and attempts to extend to his whole readership.
I was also bit irritated by his ongoing attempts to cast himself as lowbrow, working class, anti-elitist, etc. He may be genuinely uncomfortable being a part of a cultural elite(and some sincere confrontation with this discomfort could have been really interesting in this context), but he is, and he’s not fooling anyone with his protestations and poses to the contrary.
Finally, he should just avoid writing about the internet or gaming or computers, because he just doesn’t have any expertise in those areas and catty condescension is not enough to make up for that fact.