>It's referenced all over the place, all the time... on TV
>shows and everything. Wyclef remade it... didn't Coolio do so
>too? (of course, that's all ancient history for them too)

Ancient wack ass history to those kids. It's really a great thing if they don't remember those travesties.
>
>Mt parents didn't play Bing Crosby records when I was a kid,
>but I got Bing Crosby references even when I didn't really
>know who he was because they permeated the entire culture. I
>knew a lot of 1940s references without fully understanding
>them because of WB cartoons... and TV was still running reruns
>of old shows from the 1950s at that time.

You made a key point though. You knew some of them without fully understanding what they meant. We're all assuming that no one in that audience knew anything about the reference when it's quite possible that if someone played the full song for them they might hear it and say oh yeah I've heard this but they just don't know it off the top of the head.
I just think we aren't being honest with how self centered and time specific all teenagers are (including ourselves at that age) and we want to act like we were so much more knowledgable when we were that age. I laugh now thinking how me and all of my friends referred to Grandmaster flash as old school compared to Run DMC and now in retrospect they were barely a couple of years apart from when we heard each of them.