* The Player ( http://www.imdb.com/title/tt0105151/ ) - Silicon Valley these days isn't much different than Hollywood. In Hollywood, writers pitch potential hit movies to producers. In Silicon Valley, entrepreneurs pitch potential hit websites and apps to VC's. When Paul Graham talks about "x meets y" ( http://www.paulgraham.com/investors.html ), this is the movie he's probably thinking about.
* Ed Wood ( http://www.imdb.com/title/tt0109707/ ) - Ed Wood made bad movies. But God love him. He had a passion for making bad movies, had fun making them, and somehow managed to talk people into investing in those movies.
* The Hustler ( http://www.imdb.com/title/tt0054997/ ) - "Fast Eddie" doesn't lose because of his lack of talent but rather his lack of character.
* Almost Famous ( http://www.imdb.com/title/tt0181875/ ) - People that get ahead don't usually get there by clawing their way to the top. They get ahead by the assistance of people that helped them pretty much just because they felt like it.