The role of David was originally intended for Val Kilmer.
The role of Diana was first offered to 'Roberts, Julia', who turned it down.
John Cusack and 'Charlie Sheen' turned down the role of David Murphy.
John Gage's tale of his encounter with an attractive woman on a NYC Subway was taken nearly verbatim from a similar speech in Citizen Kane (1941).
Diana is reading "The Firm" by John Grisham, which Paramount Pictures soon afterwards filmed as The Firm (1993). The secretary at the real-estate office where she works is reading "Backlash", a book which criticizes director Adrian Lyne for his portrayal of women in previous films.
Director Adrian Lyne and star Demi Moore often fought on set over her character, with Woody Harrelson trying to be mediator between the two. Lyne had argued that he wanted Moore to show vulnerability, while the actress defended herself. It was later while Lyne was editing the film that he realized she was portraying what he wanted all along, which he soon apologized to the actress.
Halle Berry auditioned for the role of Diana Murphy.
During the auction scene, Redford's character is to leave the room. Redford kept missing his cue because he was listening to the jokes auction MC Billy Connolly was saying.