I've heard there's a sequel to the OP's film but I haven't seen it yet. I only bring this next suggestion up because I think it haunts me in a way a no single viewing could resolve. Then again, I don't know I've made it through a single viewing so this may just be a case of "I can watch a part of it and then try it again and again until my brain works out some kind of accurate mosaic of the entire thing." Even then, I doubt I'd describe that as understanding.
Some movies give up all their treasure on the first viewing. But others only really start to speak to you when you've already seen them once or twice. What's your favorite movie that has to be seen more than once to be understood?
Please include a picture, a poster or a clip for this marvelous film. And mention the title, and what you got from a second or tenth viewing that you didn't get from the first.
Top image: Terry Gilliam's Brazil.