There is lots of movies, I do disagree that keeping up with current ones is hard, or rather, I tend to let 99% slip by, except ones I feel I need to see on the big screen, which isn't often.
The way I go about t is, steady stream of older stuff, leave newer stuff to brew, if n a couple, few or more years its still something that sounds like it needs a watch, get to it.
For the most part, all these amazing must see movies are non entities after a while. The ones that hold up are not too many.
I really like movies from the late 60s to mid 70s and there's a lot f them, so I'd probably choose something from then, over the latest thing, although I love movies from all decades.
Depends on my mood.
My to watch pile here at home would be in the thousands, and always growing, not a list, a physical presence in my room, as more people send me movies I have to see. If they stopped making movies today, I'd never run out in my lifetime, so no big deal.
As to good movie choices for you whipper snappers, I guess the best thing is finding someone/s who have similar tastes. Some people who I like a lot recommend movies to me, and I put n the DONT BOTHER pile as I don't trust them, whereas others I know share similar taste and all I need is a heads up.