I have also seen Dr. Strangelove, or How I Learned to Stop Worrying and Love the Bomb, 2001: A Space Odyssey, A Clockwork Orange, The Shining, and Full Metal Jacket. I'd say all but one of those films is great, but I'll wait until you get that far.
I think those are also the only 5 of his that I've seen, although I don't remember The Shining
very well. (I've seen the Simpsons
parody far more often.)
is a great dark comedy.
Full Metal Jacket
has lots of great scenes and R. Lee fucking Ermey!
However, the extreme disconnect between the 1st & 2nd halves of the film doesn't help it any.
I'll be honest and say I hate 2001.
The stuff with Dave & Hal is interesting but the rest of it is so damn slow and seems designed to only appeal to stoners.
A Clockwork Orange
may be one of the most unique films I've ever seen. It's a scathing social satire and yet it's not really trying to be funny. I also think, for such a beloved movie, it's totally misinterpreted by most people. Most reviewers & commentators focus on the violence of the movie. And while the movie is, by necessity, violent, they miss the point of why the violence is there. To me, the point of the movie distills down to two things: (1) Alex deLarge commits heinous acts of violence because he has a sociopathic lack of empathy for the world around him. (2) He lacks empathy because he lives in a world that is not worth empathizing with.