Harry Burns (Billy Crystal) meets Sally Albright (Meg Ryan) after they both graduate from university and share a car ride from Chicago to New York City. Along the way, they argue about the differences between men and women and Harry says that they can never be friends because sex always gets in the way, to which Sally disagrees. She finds him obnoxious and he thinks that she’s too uptight. Once Harry and Sally arrive in New York and go their separate ways, they figure that they will never see each other again. Over the years, Harry and Sally run into each other again during various stages in their lives and become friends. The film chronicles the development of their relationship.
In 1984, Rob Reiner, producer Andrew Scheinman and writer Nora Ephron met over several lunch meetings to develop a project together. The second meeting transformed into a long discussion about Reiner and Scheinman’s lives as single men. The next time they all met, Reiner said that he had always wanted to do a film about two people who become friends and don’t have sex because they know it will ruin their relationship but have sex anyway. Ephron liked the idea and Reiner put a deal in place at a studio. She then proceeded to interview him and Scheinman about their lives in order to have material to draw on. These interviews also provided the basis for Harry. In Ephron’s first draft, Harry and Sally did not end up together at the film’s end, which she felt was “the true ending,” as did Reiner until he met his future wife while making it and changed his mind.
At the time, Reiner was constantly depressed, pessimisitic yet very funny. Sally, in turn, was based on Ephron and some of her friends. When Crystal came on board the film was called Boy Meets Girl, and he made his own contributions to the script, making Harry funnier. Crystal “experience[d] vicariously” his best friend Reiner’s return to single life after divorcing comedienne and filmmaker Penny Marshall. In the process, he was unconsciously doing research for the role of Harry. During the screenwriting process, when Ephron wouldn’t feel like writing, she would interview people who worked for the production company. She also got bits of dialogue from these interviews. She worked on several drafts over the years while Reiner made Stand By Me (1986) and The Princess Bride (1987).
When the film started to focus too much on Harry, the classic deli scene was born. Crystal said, “we need[ed] something for Sally to talk about and Nora said, ‘Well, faking orgasm is a great one.’ Right away we said, ‘Well, the subject is good.’ and then Meg came on board and we talked with her about the nature of the idea and she said, ‘Well, why don’t I just fake one, just do one?’” Ephron suggested that the scene take place in a deli and it was Crystal who actually came up with scene’s classic punchline, “I’ll have what she’s having,” spoken by Reiner’s mother. At a test screening, Reiner remembers that all the women in the audience laughed during this scene while all the men were silent. Originally, Ephron wanted to call the film, How They Met and went through several different titles. Reiner even started a contest with the crew during principal photography – whoever came up with the title won a case of champagne.
The film’s dialogue has a ring of honesty to it, from Harry and Sally’s discussion about having good sex early on in the film, to their conversation about fake orgasms during the famous deli sequence. One memorable scene is when Harry tells Sally what all men think about after having sex: “How long do I have to lie here and hold her before I can get up and go home? Is thirty seconds enough?” Disgusted, she replies, “That’s what you’re thinking? Is that true?” Harry tells her, “Sure. All men think that. How long do you like to be hold afterwards? All night, right? See, that’s the problem. Somewhere between thirty seconds and all night is your problem.” What they talk about and how they do it really captures the way men and women talk to and about each other. Much of the dialogue is also very funny. For example, there’s the little asides, like Sally’s anal-retentive and very particular way of ordering food at restaurants, or the Pictionary scene where Harry’s best friend Jess (Bruno Kirby) ineptly guesses Sally’s drawing as “baby fishmouth” (?!). Crystal’s reaction to Kirby’s guess is absolutely priceless.
The film finds humor in painful situations, like when Harry tells Jess that he’s breaking up with his wife because she cheated on him. Jess tells him, “marriages don’t break up on account of infidelity. It’s just a symptom that something else is wrong.” Harry replies, “oh really? Well, that symptom is fucking my wife.” The film is also chock full of brilliant observations about relationships – easily the best of its kind outside of a Woody Allen film. This is something that is missing from so many romantic comedies now. Most contemporary ones feel the need for some kind of zany premise to justify their existence and feature crude humor instead of working at creating fully-realized characters and authentic sounding dialogue. This is one of the strengths of When Harry Met Sally... because many of the situations and dialogue were based on the real-life experiences of the creative team that made the film.
Because When Harry Met Sally... is so character and dialogue-driven, many forget just how beautifully shot a film it is, thanks to Barry Sonnenfeld, who got his start with the Coen brothers. The establishing shot of New York City early on shows the iconic skyline bathed in golden sunlight. There is another scene where Harry and Sally walk through Central Park and are surrounded by fallen leaves that perfectly capture the city in autumn. The sequence is saturated in warm yellow, reds and browns. These shots and the locations used in the film are captured in such loving detail by someone who is a native of the city, as Reiner was at the time.
I have a yearly ritual of watching this film between Christmas and New Year’s because part of the film is set during the holidays. There is a nice montage of New York during winter: people window shopping, sledding in the park, the streets covered in snow and Christmas decorations, and Harry and Sally getting a tree. Not to mention, the film’s climactic moment takes place on New Year’s Eve.
The casting for this film is perfect. Billy Crystal’s character is definitely cast in the neurotic Woody Allen mould with his obsession with death. For example, he tells Sally early on that when he buys a book he reads the last page first so that if he dies before finishing the book he’ll know how it ended. However, Crystal is infinitely more charming than Allen and has a certain vulnerability that is attractive. Meg Ryan is adorable as Sally, bringing a perky, irrepressible charm to the role. She compliments Harry’s pessimism. Ryan also nails Sally’s need to control every aspect of her life as typified by the way she orders food at a restaurant. She is the epitome of practicality as typified by the argument she has with Harry about who Ingrid Bergman should’ve ended up with at the conclusion of Casablanca (1942).
They are ably supported by Bruno Kirby and Carrie Fisher as their respective best friends. Not only do they play well off Crystal and Ryan, but also each other once their characters become a couple. Fisher’s scenes with Ryan where they speak honestly about their respective relationships have an honest feel to them. When Sally tells Marie that she broke up with her boyfriend, her friend laments, “you had someone to go places with. You had a date on national holidays.” They talk about dating and Fisher demonstrates fantastic comic timing, like when she goes through her Rolodex of available men and when told that one is married, folds over the corner of the index card with his contact information and puts it back – you know, just in case.
A memorable scene with Kirby includes the blind date where Harry tries to hook Jess up with Sally but he ends up getting involved with her best friend Marie. They are at dinner and Marie ends up quoting a line out of one of Jess’ restaurant reviews and his reaction is so real and genuine. I would have loved to have seen a film from the perspective of Jess and Marie showing how their courtship and marriage played out. This was one of the late-great Kirby’s most memorable roles and watching him in this film again serves as a sad reminder just how poorer cinema is with his passing.
Columbia Pictures released When Harry Met Sally... using the “platform” technique which involved opening it in a few select cities and then gradually expanding distribution over subsequent weeks. Crystal was worried that the film would flop at the box office because it was up against several summer blockbuster films, including Batman (1989) and Indiana Jones and the Last Crusade (1989).
When Harry Met Sally... was not only a commercial success but a hit with critics. Roger Ebert called Reiner "one of Hollywood's very best directors of comedy," and said that it was "most conventional, in terms of structure and the way it fulfills our expectations. But what makes it special, apart from the Ephron screenplay, is the chemistry between Crystal and Ryan.” The Washington Post’s Rita Kempley praised Meg Ryan as the "summer's Melanie Griffith – a honey-haired blonde who finally finds a showcase for her sheer exuberance. Neither naif nor vamp, she's a woman from a pen of a woman, not some Cinderella of a Working Girl.” USA Today gave the film three out of four stars and wrote, “Crystal is funny enough to keep Ryan from all-out stealing the film. She, though, is smashing in an eye-opening performance, another tribute to Reiner's flair with actors.” However, in her review for The New York Times, Caryn James described the film as "often funny but amazingly hollow film" that "romanticized lives of intelligent, successful, neurotic New Yorkers." James characterized it as "the sitcom version of a Woody Allen film, full of amusing lines and scenes, all infused with an uncomfortable sense of déjà vu."
When Harry Met Sally... doesn’t answer the question about men and women being friends because it is more concerned with the differences between the sexes. Harry and Sally spend most of the film trying to under one another and find themselves attracted to each other’s idiosyncrasies that one finds endearing only after you’ve gotten to know someone over a long period of time. This film is arguably the best thing that Crystal, Reiner, Ryan and Ephron have ever done. Crystal went on to make several decent if not exactly memorable films (except for City Slickers). Reiner has made one increasingly forgettable film after another (Rumor Has It, Alex and Emma, etc.). Ephron and Ryan teamed up again for Sleepless in Seattle (1993) which was a monster hit, and You’ve Got Mail (1998), but both films don’t quite resonate as well or as memorably as When Harry Met Sally...
“It All Started Like This.” When Harry Met Sally… Collector’s Edition DVD. 2008.
Keyser, Lucy. “It’s Love at the Box Office for Harry Met Sally…” Washington Times. July 25, 1989.
Lacey, Liam. “Pals Make Buddy Picture.” Globe and Mail. Jul 15, 1989.
Peterson, Karen. “When Boy Meets Girl.” USA Today. July 17, 1989.
Weber, Bruce. “Can Men and Women Be Friends?” The New York Times. July 9, 1989.
“When Rob Met Billy.” When Harry Met Sally… Collector’s Edition DVD. 2008.