Magnolia
I was originally going to try to limit this to one movie per director but fuck that, this movie's way too good to just leave sitting on the table. I think what's most interesting about it is how close it really comes to just being a complete and total trainwreck. I mean, holy shit, there's a scene where all the characters stop what they're doing to sing along with an Aimee Mann song! And then later, just when you think it couldn't possibly push any farther into the realm of the ridiculous, it starts raining frogs. This should be a laughable, embarrassing mess, but somehow it all works beautifully.