- Doing It for the Art: Anjelica Huston and John Cusack accepted much less than their usual fees just to be in this movie.
- Promoted Fanboy: John Cusack was a big fan of the book, and tried to option the rights when he was still in high school.
- Star-Making Role: For Annette Bening, who was just two years removed from her feature film debut (in The Great Outdoors) and received her first Oscar nomination.
- Those Two Actors: Jeremy Piven and Gregory Sporleder (who play two of the sailors Roy cons in the dice game on the train) also both appeared with Cusack in Say Anything....
- What Could Have Been:
- The studio wanted Martin Scorsese to direct the film himself, but he personally chose Stephen Frears to do the job, while Scorsese stayed on as Producer.
- Sissy Spacek met with Stephen Frears to discuss the part of Lilly. Cher and Geena Davis also turned it down, while Lily Tomlin was considered.
- Melanie Griffith and Michelle Pfeiffer were considered for Myra.
- John Cusack beat out Robert Downey Jr. for the role of Roy.
- John Ireland auditioned for the role of Bobo Justus.
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