Schizopolis by Steven Soderbergh. Made after Sex, Lies and Videotape made him famous, it's a wonderfully playful meditation on all sort of things. I think the thing I most appreciate is the play with language, as in these clips with meta-language: https://www.youtube.com/watch?v=Pct9smNM6u4 (The whole film isn't like this - just these excerpts).

Apparently it got such a frosty reception at Cannes after he was so lauded for SL&V that he added the amusing introduction that includes the lines "When I say this is the most important motion picture you will ever attend, my motivation is not financial gain, but a firm belief that the delicate fabric that holds all of us together will be ripped apart unless every man, woman and child in this country sees this film - and pays full ticket price, not some bargain matinée cut-rate deal. In the event that you find certain sequences or ideas confusing, please bear in mind that this is your fault, not ours. You will need to see the picture again and again until you understand everything.": https://www.youtube.com/watch?v=qU_na__nfSU