Everyone in the late teens to early 20s has a Bill Hicks phase, but since he died in the 90s there are a lot of references to cultural moments I was a little too young to understand.
Talking about Rodney King and Reginald Denny, he managed to frame the scenario and bring humour to it. While I knew about the LA riots, it was only when I was into my 30s that I actually knew how he was talking about.
Another: In The Sopranos, Big Pussy mentions Johnnie Cochran (while threatening someone, obviously). Again, the delivery was always funny to me but I didn't know who he was until I learned about the OJ trial; something else I was aware of but too young to understand.