10) The Player
The Player is known mostly for its famous opening tracking shot, which stylistically as well as through the dialogue serves as a reference to long takes from film history as seen in Touch of Evil or Rope (as well as others less famous that the sequence also nods to), but like those films to which it refers, it is more than a mere technical cinematic achievement. It sets the tone for a movie that is self-referential and satirical, drawing attention to the fact that it’s employing a long take as it does so, and later drawing attention to the plot of the movie itself by having characters pitch the story of the film to executives within the movie (a little bit like Adaptation). It features a celebrity cameo every minute or so and paints a portrait of the two-faced nature of movie industry players, sort of like if Entourage was a little smarter.
Making movies about movies can be a bit of a catch-22, wherein detailing every little feature of the life of the filmmaker (in the broadest sense of the term) may be only interesting to those in the know and alienating to the general audience, while at the same time showing too much disdain for the people making up the bulk of your potential future collaborators could, well, affect your work prospects in the years to come. Then again, I have no idea. Pretty much everything I know about the process of making movies I learned from the movies.