- Actor-Inspired Element: Sigourney Weaver suggested dressing Ms Maddress up like Mrs Danvers from Rebecca - a film where the housekeeper is antagonistic towards her employer's new wife.
- Awesome, Dear Boy: Sigourney Weaver did the movie primarily so she could do the "Back in the USSR" scene (as well as finding the script funny).
- The Cameo: Carrie Fisher has one as Max's lawyer during her divorce from Dean.
- The Cast Show Off: The card trick Paige does in the restaurant was taught to her by stage magician Ricky Jay. She learned more tricks, but couldn't do them as she broke her finger during filming.
- Creator Cameo: David Mirkin, the director, plays Jack's lawyer.
- Development Hell: The movie was in pre-production for years, with dozens of cast and crew members dropping in and out.
- Playing Against Type:
- Sigourney Weaver usually as dramatic heroines or Mama Bear types. Here she plays a Mrs. Robinson seductress who doubles as an Unsympathetic Comedy Protagonist.
- Jennifer Love Hewitt was better known for wholesome roles or at least an Innocent Fanservice Girl. Here she tries her hand at being a Jerk with a Heart of Gold, who is now a Shameless Fanservice Girl.
- Jason Lee usually plays foul-mouthed man children. Here he's the Only Sane Man of the group.
- What Could Have Been:
- Early stages of production had Alicia Silverstone as Paige, later replaced by Jennifer Aniston, and Cher as Max.
- Norman Reedus was offered the role of Jack, but turned it down.
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