movies

A lot of things that were once creative experiences have been redone to death to the point that it can be difficult to understand what the whole hubbub was with the original.
So, yes, you have to think of it in the context of the era, which may require looking up what was made at the time, what had come before and what came after. It's a bit like paintings or other pieces of art, some of them are interesting beyond what they just represent, but for what they introduced in the world as a statement when they were made (which, admittedly can sometimes be a bit obscure). There too, a little work on the public's part is required to understand why one piece and not another is usually held in high regard (you're then totally free to disagree, or not enjoy it, but context matters quite a bit).

That right there is the millennial experience.

So many culturally defining movies came out before the 1980s that by the time you're being raised in the 90's, they're making children's media that references it. I knew the plot of Star Wars long before I saw it.

My favorite example is The Mask of Zorro, which...not an old film, but it came out when I was slightly young for it. A few years go by, I'm in high school, and Shrek comes out. Then it's sequel, with a swashbuckling orange cat voiced by Antonio Banderas. And then I eventually catch Mask of Zorro, and laugh through the entire thing because holy shit the main character sounds exactly like Puss In Boots.