Doing It for the Art: Bruce Willis wasn't paid for the movie. His salary would have nearly doubled the film's budget, and he wanted to work with Gilliam badly enough that he opted for a cut of the box office receipts instead.
Done in universe by Dr. Railly, when she sees Cole in a photograph from World War One, which was the first step to convincing her that Cole may be from the future.
Playing Against Type: Along with Se7en, one of the movies that helped Brad Pitt break out of pure pretty-boy type-casting. Also, Bruce Willis's character is notably more frail than what he usually plays. This was the first movie where one of Bruce Willis' characters dies.