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Random Trivia For This Title: - Director Cameo - Nora Ephron: When Meg Ryan's character is in the kitchen in the middle of the night listening to the 'best of' radio callers, the caller 'Disappointed in Denver' is voiced by Ephron.
- David Hyde Pierce, Victor Garber, Rita Wilson and Tom McGowan have all starred in [Frasier] which is also set in Seattle
- The second of three films that Tom Hanks and Meg Ryan have made together.
- Garry Marshall was originally slated to direct the film. He is the brother of actor/director Penny Marshall, who directed Tom Hanks in Big and A League of Their Own. She is the ex-wife of Rob Reiner, who plays Jay in the film.
- The silhouette of the couple on the box of chocolates in a shop window outside Annie's house is, in fact, a silhouette of Tom Hanks and Meg Ryan.
- Parker Posey was originally cast in the movie but later cut. She appeared with Meg Ryan and Tom Hanks years later in You've Got Mail. Dennis Quaid was considered for the male lead. Jason Schwartzman auditioned for the role of Jonah Baldwin
- This film's director (Nora Ephron) wrote When Harry Met Sally..., which also starred Meg Ryan and was directed by Rob Reiner, who appears in Sleepless in Seattle.
- A pre-Seinfeld reference to the real-life "Soup Nazi": A male journalist is speaking as Meg Ryan enters an office at her newspaper, saying, "...he's the meanest guy in the world, but he makes the best soup you've ever eaten."
- The role of Annie was originally offered to Julia Roberts, who turned it down. Kim Basinger was also offered the role in the early script process, but turned it down because she thought the premise was ridiculous. After Michelle Pfeiffer, [?] Jennifer Jason Leigh and Jodie Foster declined as well, Meg Ryan landed the role.
- The scene between Tom Hanks and Victor Garber crying over the movie The Dirty Dozen was completely improvised during the take.
- Meg Ryan and Tom Hanks only share approximately two minutes screen time together.
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