The Game (1997)

Michael Douglas plays Nicholas Van Orton, a cold San Francisco banker whose younger brother, Sean Penn's Conrad, gives him an odd birthday present: entry into a game whose rules keep changing until he cannot tell where it ends and his real life begins. This is the late-1990s fear in its most expensive suit, a wealthy man discovering that his tidy, controlled world can be staged around him by people he never sees. Two years before Fight Club, David Fincher was already pulling the rug out from under a man who thought he had everything handled. The final stretch divides viewers, so judge it on the ride, which is as tense as anything Fincher has made.