The original director of this film was to be John Korty. When Korty backed out of the project at the last minute, Rob Cohen pleaded with United Artists for directing rights. Unaware of the 'Heaven's Gate' (1980) financial fiasco ahead of them, the United Artists studio agreed to let Cohen direct.
The soprano that sings Steinman's score at the midway point (when Nick leaves Jessica following his fight with Leo) is director Rob Cohen's sister who was trained in opera.
United Artists was reluctant to give first-time director Rob Cohen the privilege of directing this film because he was mostly known for producing. Rob Cohen pressed the already hard-pressed studio, the studio heads deliberated for six weeks and Rob Cohen was ultimately given the job. There was one condition: Cohen needed a back-up director in the event that he would be fired from directing. Arthur Hiller agreed to step up in the event that this happened. Luckily for Cohen, it never did happen.
The title is an allusion to the Phil Ochs song "Outside of a Small Circle of Friends" the first verse of which is, "Look outside the window/There's a woman being grabbed/They've dragged her to the bushes/And now she's being stabbed/Maybe we should call the cops/And try to stop the pain/But Monopoly is so much fun/I'd hate to blow the game/And I'm sure it wouldn't interest anybody/Outside of a small circle of friends."
The Cafeteria in the Walker Memorial Building at Massachusetts Institute of Technology (MIT) substituted for a Harvard dining hall.