- All-Star Cast: Julia Roberts may be the biggest name, but she's headlining a movie with Billy Crystal, John Cusack, Catherine Zeta-Jones, and Christopher Walken. Also along for the ride are Stanley Tucci, Hank Azaria, Seth Green, and Alan Arkin.
- Cast the Runner-Up:
- Billy Crystal actually first wrote this film during the '90s, and was going to star as Eddie. For reasons unknown, Crystal couldn't get the film greenlit until 2000. Joe Roth ended up directing and suggested Crystal was now too old for the part of Eddie and suggested he play Lee.
- The role of Gwen was originally offered to Julia Roberts, but she asked for the role of Kiki instead.
- Real-Life Relative:
- Julia Roberts' niece Emma Roberts has a blink-and-miss-it cameo as an extra in the breakfast scene.
- John Cusack's real life sister, Ann Cusack, appears in the Uncredited Role of Lee's personal assistant.
- Real Life Writes the Hairstyle: Catherine Zeta-Jones shot the film shortly after wrapping Chicago and didn't have time to grow her hair back. The long hair she sports in this movie is actually a wig. Her real hair is seen briefly during scenes depicting the production of Film Within a Film Time Over Time which is conveniently set in the 1920s.
- Starring a Star as a Star: John Cusack and Catherine Zeta-Jones as a Hollywood power couple.
- What Could Have Been:
- Robert Downey Jr. was originally cast as Eddie, but he eventually had to back out.
- Billy Crystal wanted Meg Ryan to co-star, but her personal problems made this difficult, so he picked other people for the film.
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