1. The movie is ranked sixth on the American Film Institute’s list of the 10 greatest films in the “Romantic Comedy” category.
2. Sally Albright is based on Nora Ephron, who’s optimistic, cheerful, a control freak, and the type of person who’s “just fine” with everything.
3. The very famous fake orgasm scene was filmed at Katz’s Deli on New York’s E. Houston Street. The table where the scene was filmed now has a sign above it that reads, “Where Harry met Sally… hope you have what she had!”
4. While writing the script, Reiner once said, “You know how women have a base of makeup? I have a base of depression. Sometimes I sink below it. Sometimes I rise above it.” Since Harry is based on depressed Rob, Ephron threw the line into the script, but it was cut somewhere along the line.
5. Molly Ringwald was offered the role of Sally, but was forced to decline due to a busy schedule. She would later go on to play Sally in the stage version of the film in 2004 in London. Reiner initially envisioned actress Susan Dey for the role of Sally. When she declined, he considered Elizabeth Perkins and Elizabeth McGovern, but Meg Ryan convinced him to give her the role.
6. The woman who says, “I’ll have what she’s having” after Sally’s fake orgasm is the director’s mother, Estelle Reiner. The line was voted number 33 on the American Film Institute’s list of “Best 100 Movie Quotes in American Film.” It’s the only quote on the list delivered by a non-actor and it was written by Billy Crystal.
7. Ephron was happy with how the film turned out, but was never happy with the title. She said it was the one thing she would go back and fix if she could.
8. Albert Brooks turned down the role of Harry Burns.
9. The original script called for Harry and Sally to just talk about women faking orgasms until Meg Ryan suggested Sally actually fake an orgasm at the table. Reiner loved the idea and put it into the script. It was shot many times and Ryan had to fake orgasms for hours.
10. Working titles for the movie included: Playing Melancholy Baby, Boy Meets Girl, Blue Moon, Words of Love, It Had To Be You, Harry, This Is Sally, and How They Met. Just Friends was settled on at one point before When Harry Met Sally… won out.
11. The off-camera voice that says, “Hey everybody, 10 seconds until New Year,” is Reiner.
12. Harry Burns is based on Reiner. Ephron interviewed him before production and used his insights when writing the character. Reiner was coming out of a divorce and was depressed and loving it, like Harry.
13. Harry is shown reading Stephen King’s Misery, which would become Reiner’s next project.
14. The line “But, I would be proud to partake of your pecan pie,” was improvised by Crystal which made Ryan laugh and look to her right where Reiner silently prompted her to go with it and not break character.
15. In an interview with National Public Radio on November 2, 2004, Ephron credited Ryan not only with the idea of faking an orgasm in the restaurant scene, but also with the idea of setting it in public in the first place. Reiner has admitted that, at a test screening, all of the women in the audience were laughing while all of the men were silent.
16. Director Rob Reiner and producer Andrew Scheinman are credited on some drafts of the script.
17. The segments of married couples telling the stories of how they met are real stories Reiner discovered for the film. But the actors are actors, not the real people.
18. The film highlights the characters’ lack of insight with meaningful locations. Harry and Sally are as blind to romance as they are to the love growing between them. The same logic was used for Harry’s apartment. The windows overlook the Empire State Building and the view is either the most beautiful or most lonely in the world.
19. During the last scene, Harry doesn’t understand what the song “Auld Lang Syne” is about. Some years earlier, in 1971, Rob Reiner also questioned the meaning of the song when portraying Mike Stivic on an episode of All in the Family.
20. Sally’s picky eating habits are also based on Ephron. Years after the movie came out, the writer was on a plane and ordered something very precise. The stewardess looked at her and asked “Have you ever seen the movie When Harry Met Sally…?” Sally’s picky eating habits were put into the movie after Reiner saw Ephron ordering food in a restaurant. When he brought it up, Ephron said, “I just like it the way I like it,” a line which was put into the movie.
21. In early 2004, the film was adapted for the stage in a production starring Luke Perry and Alyson Hannigan.
22. In the first draft of the film, Harry and Sally did not end up together. It was only later, that Ephron and Reiner decided that Harry and Sally belonged together. Although, they’ve acknowledged it’s not realistic.
23. When posed the film’s central question, “Can men and women just be friends?” Ryan replied, “Yes, men and women can just be friends. I have a lot of platonic (male) friends, and sex doesn’t get in the way.” Crystal said, “I’m a little more optimistic than Harry. But I think it is difficult. Men basically act like stray dogs in front of a supermarket. I do have platonic (women) friends, but not best, best, best friends.”
24. The orgasm scene was edited out of airline prints of the movie.
25. Included among the “1001 Movies You Must See Before You Die”, edited by Steven Schneider.
26. Rob Reiner, Nora Ephron, and Andrew Scheinman chose beautiful locations to highlight the characters lack of insight – Harry and Sally are as blind to romance as they are to the love growing between them. The same logic was used for Harry’s apartment. The windows overlook the Empire State Building. It could either the loveliest – or – loneliest, view in the world.
27. During the end scene Harry mentions never understanding what the song Auld Lang Syne was about. Some years earlier Director Rob Reiner also questioned the meaning of the song when portraying Mike Stivic on an episode of All in the Family (1971).
28. When Harry Met Sally… was the 11th most lucrative film of 1989, ahead of The Little Mermaid, Christmas Vacation, Uncle Buck, and Field of Dreams.
29. Nora Ephron wrote the screenplay – and its numerous drafts – over a period of nearly 5 years.
30. The When Harry Met Sally… soundtrack features a then unknown Harry Connick, Jr. Bobby Colomby, the drummer for Blood, Sweat & Tears, was a friend of Reiner’s and recommended Connick. Reiner was struck by the pianist’s voice and how he sounded like a young Frank Sinatra.
31. Harry and Sally’s final interview at the end of the film was completely improvised.
32. Naming the film proved to be problematic. At one point, Rob Reiner ran a competition amongst his Castle Rock employees, looking for suggestions.
33. The scene where we see all four lead characters talking to each other individually on various telephones took 60 takes to nail.
34. The man that Sally is kissing at the airport when Harry runs into them is played by Steven Ford, the son of former President Gerald Ford.
35. The Pictionary scene was entirely improvised.