But in general, time is a pretty good filter for quality (you’ll miss some good stuff, but if you only look at the culturally remembered stuff, you’ve still probably got a lifetime of good media)
So many reasons. Pre 2000, music was tightly controlled, the bar was quite high, and though there was still crap, there was good stuff, and it was backed hard by the industry. Everyone knew what the 'top 10' was at the time and everyone was on the same page.
Now with so much diversity, it's hard for something to really break through.
There are countless other reasons as well we could go into, but we truly live in a different kind of era.
Take a look at Billboards Top 100 for the 80s and 90s and see how much you recognize. The bar wasn't very high at all.
It's been years since I've heard anyone listen to or talk about Nirvana, Pearl Jam...
"If a book has been in print for forty years, I can expect it to be in print for another forty years. But, and that is the main difference, if it survives another decade, then it will be expected to be in print another fifty years. This, simply, as a rule, tells you why things that have been around for a long time are not "aging" like persons, but "aging" in reverse. Every year that passes without extinction doubles the additional life expectancy. This is an indicator of some robustness. The robustness of an item is proportional to its life!"