So, here are the five films I have watched more than any others basically to the point where I have occasionally suffered some burnout...
1. Dr. Strangelove - I can't tell you how much I love this picture. Over the years I have learned more and more about it and why Kubrick made it and how his fear of nuclear destruction was not only very real but damn near drove him to move to Australia due to his discovery during his research of the topic that it may have been at the time the safest place to be if Russia and the United States launched an attack on each other. Basically, I've come to feel this film covers most of what is right and wrong with the world and how despite our best intentions, due to our being aware that we exist for only a limited amount of time, we are pretty much obsessed as a species with our own annihilation. It's both dark and hilarious in wonderful ways and stands as, in my opinion, one of the most brilliant films ever made...as an entertainment, satire, and social commentary. Everything wonderful about filmmaking to me is contained in this picture.
2. Apocalypse Now - A friend and I managed to sneak into this picture when I was just 12 years old. I had no idea what it was about at the time but the title intrigued me and I thought it was a horror film about the end of the world. Turned out that's pretty much what it was to me at that point. It seemed to cover some of the same ground as Strangelove except without the laughs. I did not know it was based on Conrad's Heart of Darkness at the time and had not yet read the book but I did feel that the film exposed to me how dark the hearts of men could be. I first purchased this film on VHS and my friends and I watched it over and over and over again. On roads trips in high school and college we would quote from the film constantly. The film to me was never about the Vietnam war but really about, again, how humans as a species go utterly insane when we stand too close to our own true nature. I think that trip up the river is about how any society walks a very fine line between coexistence and utter chaos.
3. The Good, the Bad, and the Ugly - So, watched this every time it was on television as a child. Then got to see it on the big screen in my teens. It was not until I was in my teens that I realized that Clint Eastwood's character is not really a "good" guy and is really just another obsessed mercenary caring little for anybody other than himself and fattening his wallet. In a way the film is a great metaphor for what would become of the United States. Perhaps as an Italian Leone saw this quite clearly and so the three characters in the film just represent our greed and vicious pursuit of cash above all else. Sure, the three characters and their methods may seem a bit different but they are all after the same thing.
4. Jaws - This has been a summer tradition for me pretty much going back to when I saw it in a theater in 1975. Basically, I think I have suffered complete burnout with this film and have taken a break from it. It is not at all a complex story but it has lots of great little moments and the acting in the film is pretty awesome all the way around. Although mostly known as a "horror" film about a very big and very hungry shark the film is really about men coming together to solve a problem. The three leads are all quite different and they all bring different things to the table and they manage to overcome their differences, pool their strengths and win the battle. Now we all know the three leads in the film but Murray Hamilton as the mayor basically steals every scene he is in and gives a performance better than any supporting actor nominated for an academy award in the past 3 decades. Wow, is he awesome in this! So really, this is an ensemble acting piece masquerading as a horror film about a hungry shark.
5. Network - My obsession with this film began in the 1980s. I did not see Network in a theater in 1976. Even if I had I would not have likely grasped how brilliant this picture is. I was a freshman in high school when I first saw this picture and boy did it leave a mark. Basically, it touched upon something that Strangelove and Apocalypse also addressed...that as human beings the line between being sane and absolutely bat shit is mighty thin. Not to mention it perfectly predicted the rise of something like FOX News. We don't get much great satire anymore as it seems to be something people now just do not like. There have been some good ones like Thank You for Smoking or I Heart Huckabees (both of which desperately need a blu-ray) but they mostly go totally ignored by the general public.
Great list! As someone said before, simply too many to name.