2001 A Space Odyssey (1968)

I first saw this movie on cable TV when I was fifteen. Despite the hours of ultra-repetitive commercials that I was subjected to and the fact that it aired pretty late, I was hooked. I'll never forget the utterances of sheer agony and bewilderment that came from my mouth when the credits rolled as my Dad laughed knowingly behind me.
This film can only be described as a psychedelic sci-fi ballet. Every moment is beautifully choreographed and painstakingly wrought. Stanley Kubrick's use of music is, of course, the things that legends are made of. It is a study in the beauty of contrast and an explanation of how to represent themes without even saying a word. 
I love that the film starts out as any good film should, at the beginning...the very beginning. We then get to see where millions of years of evolution has left our species. The acting was subtle and understated and provided a great foil upon which the viewer can truly appreciate the world created for them. 
HAL 9000 is one of the greatest characters ever written, hands down. Who knew that a single red light bulb could be so intimidating and interesting. The other characters were all fairly stereotypical, the shady politician, the all-American astronaut, and uh, monkeys. They were there to show that even though we have evolved so much, even though technologies have increased beyond any one's wildest dreams, we still fit the basic human molds.
Honestly, I have no idea what happened in the end or what the hell was up with those obelisks. Really though, I don't care to know. My only complant is the utter contempt in this film for any kind of pacing. I know that often times, yes, that was the point, but it did get tedious after a while. In the end though, the movie is a wonderful trip and even though I don't quite understand it, I think that it is just fine that way.