You make some good points. And Princess Bride is a solid choice.
The idea is two fold, and I didn’t explain it well- Films that qualify as great and are culturally important outside of the film itself, films that people will casually quote or that have spawned a genre.
A Fistful of Dollars (1964) - Note that it’s a remake of Yojimbo (1961) – itself a remake and often acknowledged as having been inspired by The Glass Key (1942) - and was remade several times afterward.
Witness For The Prosecution
The Apartment
Down By Law
Treasure of the Sierra Madre
Beat The Devil (a personal favorite that gets mediocre reviews).
Adam’s Rib.
Kind Hearts and Coronets (or substitute any Alec Guinness film of that era).
Anything with Peter Lorre and/or Sydney Greenstreet.
I misunderstood and thought we were looking for “must-see films” rather than “must-see films for pop culture knowledge”. For that, I think you would need to throw in at least one Jackie Chan film (any will do), at least one 80s action film (Predator is the definitive one), Groundhog Day, Inception, Titanic, and Avatar (with the big blue people). I can’t recommend those last two as good stories.
No, you had some good ideas there. Yeah, mostly the “must-see films for pop culture knowledge”- films that when quoted around the gaming table or when having lunch are hopefully films which have been seen.
I saw The Graduate for the first time about two or three years ago and I thought it was absolutely fantastic and funny as hell in that understated dark comedy sort of way. Exactly the type of humor I love.
Cool Hand Luke Butch Cassidy and the Sundance Kid The Sting Three Days of the Condor The Three Faces of Eve Les Ripoux One Flew Over The Cuckoos Nest Misery Marathon Man Super Troopers
My top 10: Rear Window (could have easily picked other Hitchcock films like Dial M for Murder) Schindler’s List (a must see for historical understanding as well as the movie quality) The Godfather (really can’t include I and not II) The Godfather II The Longest Day (greatest cast ever) North by Northwest The Exorcist (greatest horror movie of all time) 12 Angry Men (1957) Jaws (the king of the summer blockbusters) The Shawshank Redemption
Near Misses Apocalypse Now Lolita (1962) Mulholland Drive (what can I say, I think Lynch is a genius) Ben Hur (1950) (best spectacle movie)
I certainly am not unbiased, I prefer some directors and genres much more than other.
I find old movies amusing. When you watch them you feel like you are in a museum. If you are looking for that new yet old feeling i recommend:
Hellraiser 1979
Halloween 1978
Terminator 1984
Alien 1979
Also, if you watch Scream 1996 after Halloween, you get a very unique experience. Scream has plenty of refrerences to Halloween.