Capitalism: A Love Story (Michael Moore, 2009) 
While I agree with a lot of what Moore is saying, he never gets all these ideas together to make a fine-tuned film. The film is too scattershot, with no real firm philosophy other than showing the ills of capitalism. It jumps to so many circumstances and ideas, from stories of specific people to Wall Street, that it suffers from a lack of focus of just what Moore is trying to say. On one level, the film is saying that true democracy is the cure for capitalism but isn't that the same system that has allowed capitalism to corrupt it? Moore calls for action but other than a call to action, he never gets specific. The most interesting parts of Moore's work, his attention-grabbing antics, fall flat for the most. Obviously, Moore wants to explain a corrupt system but he's ended up with a film preaching to the choir.
Also, there is the whole 'Michael Moore is a hypocrite' argument that comes out of this. Because Moore is making a film about how bad capitalism is while it has made him a millionaire, that on the surface makes him seem like a hypocrite. I will defend him to the extent that he's just working in the system that's been established. I do happen to think there is a big difference between someone who has become wealthy as an entertainer than as someone operating a corporation or lawyer or whatnot. Moore has become wealthy because people have chosen to see his films or read his books. He's not exploiting workers, or taking their jobs away, or profiting off of other's peoples' misery, tragedies, etc. So really Moore's film is attacking a form of corporate capitalism that has made him wealthy, almost in despite of itself. At least give Moore some credit for using his high-profile position to address some economic issues that more people should be paying attention to.