Not a bad list (though movies like The Departed, Sin City, Troy, Harry Potter, Pirates otC, The Craft, 300, Sleepy Hollow, Castaway, Scarface [another remake btw] and some others I consider to be some really terrible/some of the worst!) If you're open to such a variety of film, you should really just toss your pre-judgement of older movies out the window and open up to the idea that they can be really good. Movies really started to come into their own in the mid30s and come the 40s they were producing a lot of great stuff (even older stuff can be great, really!), and there are SO many great movies from varying eras that you're just disregarding for no real reason. Please check out: The Killers (then check out the remake from the 60s, wayyyy better than any of the remakes on your list, they remake movies now out of lazy unimaginitive-ness rather than try to reinterpret or re-envision something for a modern era and remake it well), Kiss Me Deadly, M (Fritz Lange, an incredible director), Double Indemnity (Billy Wilder), Kiss of Death, Treasure of the Sierra Madre, 400 Blows, Jubal, Night of the Hunter, The Third Man, Crossfire (Robert Mitchum is great), Murder, My Sweet, Bridge Over the River Kwai, Elevator to the Gallows, Wages of Fear, The Seventh Seal (anything Bergman!), Wages of Fear, and many more!!! Also check out the older Kubrick movies I'm going to mention below. Also, get some more 70s movies in your system, like I said, perhaps the best decade for movies ever yet. The Deer Hunter, One Flew Over the Cuckoos Nest, Being There, THX-1138, Andromeda Strain, Chinatown, Texas Chainsaw Massacre, Apocalypse Now, Escape from Alcatraz, Soldier of Orange, Rollerball, Deliverance, and many more!
From other decades: The Great Escape, Easy Rider, Z, My Dinner with Andre, Fanny and Alexander, Midnight Cowboy, Once Upon a Time in the West, oh shit I better stop...
Matewis: Interesting, I've never really thought of the film, or tried to watch it, with such a meta interpretation in mind. I suppose that that could affect how much one enjoys the film, or any other film interpreted similarly. But like you said, it also depends on your palate, which is perhaps why I think I didn't really enjoy the film.
As for his other stuff, come to think of it, I haven't really seen that many of his other films: only Full Metal Jacket and Space Odyssey, both of which I loved. Hmm, I really should fix that. Think I'll start with The Shining, and move onto Dr Strangelove.
Ohyes, there's a lot packed into Eyes Wide Shut (it's very much an art film), as there are a lot of movies (especially Kubrick!) They lend very well to metaphor and allegory and layered meaning and social commentaries and more! I also recommend reading Arthur C. Clarke's 2001: A Space Odyssey
after watching the movie, and then reading the book again, and then re-watching the movie. Doing all that adds a lot to the depth that is already there. I probably had seen the movie 3 times before reading the book and both still blew the mind for a while after.
His catalog is quite short, I highly recommend them all, I consider them all timeless must-see classics. Killer's Kiss is probably his least great, so you could hold off on that. Paths of Glory, The Killing, Lolita, Spartacus, Barry Lyndon, A Clockwork Orange, yep!