5. The Player
A brilliant send up of the Hollywood system, this 1992 masterpiece from Robert Altman tells the story of fast moving studio executive Griffin Mill (Tim Robbins), who finds himself in hot water when he kills an aspiring screenwriter. What follows is a terrific lampoon of what Hollywood will do to get a movie made, and the emphasis of a commercial success over that of quality, a theme that is the ultimate example of art imitating (and satirizing) life. This film put Altman back on the map and has enough celebrity cameos in it to keep you playing Six Degrees of Kevin Bacon for years to come.