1. Adaptation (2002)
Possibly the most meta film of all time was almost a certain failure. When screenwriter Charlie Kauffman couldn't figure out how to adapt Susan Orlean's best-selling novel "The Orchid Thief," he did something shocking, risky, and awesome--he wrote himself into it. The film is about writing the film, with a little bit of Hollywood thrown into the mix along with pieces of Orlean's novel. What I would give to see the initial reactions to Adaptation by Kauffman's agents, the production company, and most of all Susan Orlean herself (Orlean is portrayed as a miserable woman who becomes addicted to drugs during a romantic fling with her novel's main character, none of which actually happened). The movie shouldn't work. It should alienate the audience from simply being "too weird." Well, Kauffman writes "weird" better than anyone else in Hollywood. If you've ever seen Eternal Sunshine of the Spotless Mind or Being John Malkovich (two of Kauffman's scripts) then you know that. For those of you who make fun of Nicolas Cage--please watch this film. Cage is spectacular playing both Kauffman and his fictional twin-brother Donald. I don't know what happened to Cage that brought him to where he is now (The Sorcerer's Apprentice, Season of the Witch, Drive Angry, etc.), but at the time he was possibly the best actor in Hollywood. If you consider yourself an avid fan of movies, this is one you have to see.