14. The Assassination of Jesse James by the Coward Robert Ford (2007)
The movie that gives away the entire plot in the title—how'd that one fail? Dramatically speaking, there's something really stirring about knowing the ending at the beginning of this film. Watching Robert Ford fixate on the gunslinger's persona as you watch James struggle with his notoriety and legacy is all the more moving because you know that it will all come crashing down.
After Ford does the deed, he's forced into a life that occasions further reflection on fame and legend. All of this notwithstanding, the film lost at the box office, and you can't help but wonder if it's because, when people go to movies, they go to be surprised by the film's ending.