Alright, I'm going to reveal what an arthouse snob I am with this list, but I'll try to avoid the really bizarre experimental stuff. There are plenty more that I could add to this list, but I'll try to keep it to a reasonable length.
Network: A truly vicious satire about the corporate takeover of American news media in the 70s. A lot of what it predicted has pretty much become the reality that we live with today. Not just one of the best satires ever, but also one of the best movies ever, with some fantastic dialogue and incredible performances.
Anything by Akira Kurosawa. I particularly enjoy "Ran" and "Dreams". ("Ikiru" and "High and Low" are probably closer to the type of social commentary you're asking for, but I find those films to be a little too "on the nose" for my tastes.)
Anything by Ingmar Bergman, especially "The Seventh Seal" and "The Virgin Spring".
Anything by Stanley Kubrick, with the possible exception of "Eyes Wide Shut".
Many of Terry Gilliam's films, particularly "The Fisher King" and "Brazil".
"Stalker" by Andrei Tarkovsky: a beautiflly-filmed sci-fi piece with some interesting conversations about what people think they'd wish for vs. what they actually want. The look of the game S.T.A.L.K.E.R. was heavily inspired by this, though the movie contains no ravenous mutants. :p
Unforgiven: you've probably seen it, but if not, it's basically a dark western about why we shouldn't make westerns. :p
The Noah: Largely unknown film. A lone soldier washes up on an isolated island after some unnamed disaster has probably wiped out the rest of the human race. As the film progresses, he starts to create imaginary companions (who we hear but never see) who slowly take on a life of their own, eventually forming their own civilization to which he plays the role of an increasingly disgruntled God. Some people will probably find this film insufferably boring since not much is actually happening on-screen, but I loved it.
Most Cohen Brothers movies: Fargo, Barton Fink, etc.
My Dinner With Andre. You've probably heard of this film by reputation, and yes, it really is just an hour and a half of two guys having a conversation over dinner. If you like listening to good conversations and enjoy oral storytelling, you may like this movie. If you think that sounds like the most boring thing ever, then for you, it probably will be.
Possible Worlds: When I read the description, I figured this would probably be a really wanky arthouse film, but I ended up loving it. It's an almost hypnotic movie about a guy who shifts between alternate versions of reality, and what he does when he gets there.
The Decalogue: A series of ten short (1-hour) films loosely themed around the ten commandments, but really more of a meditation on moral issues generally.
The Bird People in China: story is about a Japanese businessman and his yakuza minder who journey into the remote mountain regions of China to test the quality of a potential jade mine, and who both fall in love with the pastoral village they find there. Raises and gives serious treatment to some tough questions about the beneficial and destructive effects of technology, and whether it is necessary (or fair) to "preserve" some cultures in a primitive state. The ending is a bit of a cop-out, but the movie as a whole is beautiful.
If you're interested in documentaries as well, I'd recommend:
-Anything by Werner Herzog (The White Diamond, Grizzly Man, Encounters at the End of the World, etc)
-Anything by Adam Curtis, especially "The Century of the Self", which is a fascinating exploration of how Freud's theories were used by the Ad industry to reinvent the concept of "personal identity" repeatedly over the following century. I would note, though, that I don't know if this would resonate in the same way with those who didn't grow up in North American or British culture.
Post edited August 05, 2013 by Azilut