- Award Category Fraud: Woody Harrelson "won" a Razzie for Worst Supporting Actor, while Robert Redford was nominated for Worst Actor. Really, Harrelson was one of the main roles, while Redford was the main supporting role.
- Dawson Casting: Demi Moore and Woody Harrelson, then in their early-30's, play teenage versions of themselves in flashbacks.
- The Red Stapler: Demi Moore's black cut-out Thierry Mugler-designed dress generated such immense interest after the movie's release, it was often copied by other designers.
- Wag the Director:
- Adrian Lyne and 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.
- In the original script, rather than being insulted by Gage in order to make her leave, Diana tells him that "You can't give me what I really want. I want my husband." Apparently, this was changed because Robert Redford didn't like the idea of his character being told where to get off.
- What Could Have Been:
- Linda Fiorentino, Nicole Kidman, Andie MacDowell, Julia Roberts and Debra Winger were considered for the role of Diana. Halle Berry expressed interest, but was not even allowed to audition, as TPTB feared adding an unnecessary racial undertone to the plot. Sophie Marceau auditioned.
- William Baldwin, Tom Cruise, John Cusack, Johnny Depp, Val Kilmer, Tim Robbins, Charlie Sheen and Christian Slater were considered for the role of David.
- Jason Alexander was considered for the role of the Murphy's lawyer Jeremy.
- Warren Beatty was considered for the role of John Gage.
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