I think at least part of this is that pop culture has gotten such a longer shelf life over the past 20 years.
You can listen to a Top 40 station now and hear a song from 10 years ago easily, even songs from the 80s or 90s on special occasions (which might just be the Nineties at Noon or whatever every single day).
A Top 40 station in the 80s? Played the current fucking Top 40 and that was it. You were lucky if you heard a song that was one year old, definitely never ten. I was born in 1979 and heard almost no music from before I was born until high school or college. If you wanted to hear anything older than a year, you had to listen to a classic rock (late 60s to 70s) or oldies (50s to early 60s) station. There was nothing earlier than that on the radio.
A restaurant was playing What a Feeling, from 1983. 28 years before my son was born. That’s the equivalent of hearing a song from 1951 in the late 80s, which just did not happen. Even for an oldies station, it was hard to find anything that old.
VCRs were just getting big in the mid-80s, but there was a limited selection of videos you could buy (or even rent) for them. Most video rental stores didn’t bother to stock TV shows, it just wasn’t worth it. (Few shows were even released on VHS.)
So you could generally watch recent movies and “classics” but if you were looking for some random movie from the mid-70s - that’s only ten years previous - you were mostly out of luck. Imagine looking for a movie from 2006 right now, and you can find maybe the top-grossing ones and a few that won Oscars, but Night at the Museum? The Devil Wears Prada? You’re shit outta luck. That’s what it would have been like looking for movies from 1976 in 1989.
So for those of us who grew up in the 80s and early 90s, pop culture had a hard limit of about a decade, if that. By the late 90s, the internet was good enough that music was starting to stretch that, but you still couldn’t really get video through the internet and DVDs were still catching up in terms of what was available. You didn’t really get entire seasons of TV on DVD until the early 00s - the first season of The Simpsons, which aired in 1989, wasn’t released on DVD until 2001.
Anyhow, I think that’s why a lot of older millennials and Gen Xers are having trouble wrapping our heads around the idea that the year 2000 was almost 20 years ago. Because we grew up in a world where if you heard a song regularly, or watched a movie or a TV show that wasn’t late-night reruns, it had probably been released within the past 5 years, and almost definitely within the past 20. Our brains haven’t quite gotten used to hearing a new song followed by a 30-year-old song on the radio and not just being able to find any decade-old movie at will but seeing gifs of decade-old movies almost daily. Our brains think that means those things must still be new.
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