Mulholland Dr. is a beautiful and haunting meditation on dreams that not only comments on them but channels them. Not for youngsters as there are about 2 lesbian scenes (I preferred skipping over them).
Akira Kurosawa's Dreams was the first thing that popped into my head (despite having never seen it).
Does that make me a more "cultured" movie fan since an Akira Kurosawa film was the first thing in my mine instead of the more obvious Nightmare on Elm Street films?
Among other things it explores how dreams can be like theater rehearsals/performances. Very subtle, imaginative and entertaining, and probably nothing like any movie you've ever seen. A personal favorite.
Not yet available on DVD, unfortunately, but it does get shown frequently around here, anyway.
Vanilla Sky - I'm one of the few that loves this film The Thirteenth Floor - more of a Matrix-type scenario but very dream-like in many parts Star Trek Generations
I second the vote for Mulholland Dr. The whole thing feels like a dream, and is best interpreted in terms of dreams (much was written about it in these terms at the time). It's David Lynch, so it's hard to wrap your brain around, and most of the strange moments continue on unexplained. It blew me away, though. (And I like the sexual scenes, though there is one nudity-free dialogue scene between a man and a woman that is probably the hottest thing in the movie, and a big part of why I really like Naomi Watts.)
What's amazing about this movie is that the dreamy stuff really only came as a result of the film getting rejected as a TV pilot (it was supposed to be the two-hour first episode of an ABC series); with the story's future in serial television wiped away, Lynch decided to take a completely different approach to the material, and turned out one of my favorite movies of the last few years.
I don't think so, Chad. I thought Nightmare first, but it had already been mentioned, Dreams was my second choice. I like the Mulholland Dr. Mention. Has anyone said Lost Highway? There's another twisted little gem. Or how about Jacob's Ladder?