1Tom Hanks was originally offered the role of Harry.
Aaron Rapoport//Getty ImagesAnd, at least according to IMDB, Albert Brooks, Michael Keaton, Harrison Ford, and Bill Murray were also considered before producers landed on Billy Crystal.
2Molly Ringwald almost played Sally.
Ron Galella//Getty ImagesHowever, Meg Ryan, who had never been the lead in a movie before, was able to convince director Rob Reiner she was right for the part, and he casted her instead.
Advertisement - Continue Reading Below
3The inspiration for the movie came from the writer and director's friendship.
Columbia PicturesIn a way, Nora Ephron and Rob Reiner are the real-life Harry and Sally. Everything from their little personality quirks to their candid discussions about men and women inspired the material for the characters.
4The film was originally called 'How They Met.'
Columbia PicturesThe creative team had a tough time figuring out exactly what to call this film, so Rob Reiner held a title-naming contest, rewarding the best pitch with a full case of champagne. Nora Ephron also came up with Boy Meets Girl, Just Friends, Words of Love, and Harry, This is Sally.
Advertisement - Continue Reading Below
5Billy Crystal and Meg Ryan immediately hit if off.
Columbia PicturesThe chemistry between the stars was critical, so production knew they had to get the casting right. Once Billy and Meg got into the audition together, the chemistry was instant. Billy told Entertainment Weekly, "Meg came in, and we didn't even read a scene, and we all knew it was her. It's just one of those indefinable things that when we started talking, we were them already, you know?"
6Meg Ryan came up with the film's most memorable moments.
You know the one: Harry and Sally are in the deli discussing the topic of women faking orgasms. To prove her point, Sally demonstrates the act right in the middle of the packed eatery. Well, Meg Ryan came up with the idea for the scene, as she believed it would fit her character's behavior. Genius.
Advertisement - Continue Reading Below
7And that iconic line is delivered by someone on set's mother.
Columbia PicturesFollowing the, ehem, performance put on by Meg Ryan's character in the deli, the scene cuts to a nearby patron who tells a waiter, "I'll have what she's having." The "Older Woman Customer" (as she's credited in the film) is played by director Rob Reiner's mom, Estelle.
8The four-way telephone scene was the most complicated to shoot.
In the movie, Harry and Sally give their best friends, Jess (Bruno Kirby) and Marie (Carrie Fisher), a call for some much-needed advice. It took the four actors 61 times to get the perfect take. To pull off the synchronized act, the crew used three cameras and filmed the actors in real-time on separate sets that were all connected by a real telephone line to get the timing just right.
Advertisement - Continue Reading Below
9Billy Crystal improvised a lot of the New Year's Eve scene.
Columbia PicturesWhich ones? Billy came up with, "I love the way your nose crinkles" and "When you realize you want to spend the rest of your life with somebody, you want the rest of your life to start as soon as possible."
10The movie almost had a different ending.
Columbia PicturesEveryone loves a happy ending, which is why director Rob Reiner changed around the script's initial ending — which saw both of the title characters going their separate ways. The inspiration for the change? Reiner fell in love while making the film, so he felt the characters deserved a happier fate.
Advertisement - Continue Reading Below
11Harry eating grapes on the road trip wasn't in the script.
Columbia Pictures"I wanted to make him a little bit rougher around the edges to start. So we came up with this idea of him eating the grapes [during the road trip]," director Rob Reiner recalled. "[Billy] said, 'I can just be spitting the seeds out the window.' That's what gave Harry a little bit more abruptness. Billy and I just came up with that on set as we were doing it."
12The movie was a launching pad for Meg Ryan.
Ron Galella//Getty ImagesFollowing the success of When Harry Met Sally, the film's screenplay writer Nora Ephron (center) and Meg went on to collaborate on three more huge projects together: Sleepless in Seattle (1993), You've Got Mail (1998), and Hanging Up (2000).
Advertisement - Continue Reading Below
13One of the actors is related to a former president.
Columbia PicturesActor Steven Ford, who portrayed Harry's neighbor/Sally's boyfriend Joe, is actually the son of former U.S. President Gerald Ford. He later appeared in Armageddon, Black Hawk Down, and Transformers.
14Critics didn't give the film great reviews.
Columbia PicturesAt the time of the film's release, The New York Times called it an "amazingly hollow film," and Roger Ebert said it was "most conventional, in terms of structure and the way it fulfills our expectations." It wasn't all negative, however, as many had positive things to say about the movie's humor and the chemistry between the actors.
Advertisement - Continue Reading Below
15And Billy Crystal thought it was going to bomb.
Columbia PicturesBecause the film was opening against big-budget summer blockbusters like Batman and Indiana Jones and the Last Crusade, Billy had little hope for a big box office return. To combat the competition, the studio released the film in just a few theaters the first week to allow for positive word-of-mouth to spread — a tactic that seemingly paid off.
16Surprise! It was a box office hit.
Paul Hawthorne//Getty Images Advertisement - Continue Reading Below
17Director Rob Reiner was worried about working with Billy Crystal.
Ron Galella//Getty ImagesSometimes it's best not to mix work and play, and that's exactly why Reiner was apprehensive about working with his best friend, Billy Crystal. "The fear I had was, 'What if you would [work] with a friend and it doesn't work out, are we going to destroy a friendship?" Reiner expressed. "I had no reservations about him playing the part, I just wanted to make sure."
18A clue about director Rob Reiner's next project was hidden in the film.
Columbia PicturesIn the movie, Harry can be seen reading Stephen King's Misery. It's a non-trivial moment that reveals what director Reiner would go on to make next — the James Caan and Kathy Bates thriller was released just one year later.
Advertisement - Continue Reading Below
19One of the film's sets inspired another Nora Ephron movie.
Columbia PicturesThe Shakespeare and Co. bookstore (a.k.a. where Harry and Sally run into each other) inspired Nora Ephron/Meg Ryan's You've Got Mail.
Inspiration struck Nora when the location closed down shortly after a Barnes & Noble opened up nearby — making way for the film's commentary about large chains versus local stores.
20You can live at one of the filming locations.
Columbia PicturesThe first-floor ballroom in Manhattan's Puck Building, located at 295 Lafayette Street and Houston Street, was the setting for the big New Year's Eve party at the end of the film. The multi-use structure has luxury penthouses at the top of the building that go for a cool $36 million.

Alex is an entertainment and lifestyle writer who has a penchant for pineapple pizza, paranormal podcasts, paddleboarding, and alliteration.
Advertisement - Continue Reading Below
Readers Also Read
Advertisement - Continue Reading Below
Advertisement - Continue Reading Below