I remember growing up in the late 90's and early 00's watching every single top 100 x of the 60s/70s/80s/(and 90s to less success) special on VH1. Recently I've noticed that my generation is beginning to hit traction and reach that period where we're sort of calling the shots or our opinions are at least respected as an audience since we sort of have some money to spend now.

However, I've also noticed we're not really reflecting on the 90's or 00's like we did past decades. I haven't really been able to put it into words until I saw your post, but it is very plausible the internet has something to do with it.

Perhaps it centers around pop culture as no longer being tied to a lowest common denominator. I'm definitely not saying we've hit some cultural enlightenment by any standards. Instead, it's more like the smaller camps of popularity allow people with similar interests to find each other and congregate more easily, thus creating their own tailored pop culture. I think this is also evident when you look at a lot of people's disdain for award shows in music now. They're just not celebrated like they used to be. I guess for a lot of people pop has always been tolerated more than they care to admit and they just don't see the point anymore.

tl;dr The internet has made it easier to find people with relatable interests. This has diminished the value of pop culture as its primary function is largely seen as a media that is interesting but generic enough for everyone to find some value in and discuss with others. Therefore, the internet has made it harder to pin down exactly what defines a period or decade. I think /u/FennelSoup is right.