This article is part of our One Perfect Archive project, a series of deep dives that explore the filmmaking craft behind some of our favorite shots. In this installment, Madison Brek looks back at When Harry Met Sally and discusses how it strikes a perfect balance between heart and humor.
When Sally first meets Harry, she can’t stand him. From the earliest moments of their 18-hour drive from Chicago to New York, the now-classic rom-com couple can’t help but get on each other’s nerves; they bicker about everything from happy people to the ending of Casablanca and bristle at the other’s views about male-female friendships.
Some might call this textbook flirting, and they’d be absolutely right; “Call the cops, it’s already out there!” Harry quips after remarking that he finds Sally attractive. But these characters are also engaging in a classic comedic setup here. Just ask any road-movie, buddy-cop movie, or a combination thereof, and they’ll all show you that putting two opposing personalities in a car together is the foundation for a beautiful, hilarious partnership.
Thanks to an Oscar-nominated script from Nora Ephron, some sharp direction from Rob Reiner, and a couple of charming lead performances from Billy Crystal and Meg Ryan, When Harry Met Sally has become an essential genre entry as both a romance and a comedy. The film, which follows two Manhattanites who are determined not to let sex get in the way of their friendship, is grounded in the continuous back-and-forth banter of its central characters and the pairs that surround them — see also the film’s standout supporting performances from Bruno Kirby and Carrie Fisher or its interludes featuring the stories of real long-standing couples.
Really, onscreen comedy included its fair share of quick-witted couples before Harry and Sally ever hit the scene — think Lucy and Desi of I Love Lucy or Hildy and Walter in His Girl Friday. What makes When Harry Met Sally so special is that the central pair is such a feat of collaboration. Indeed, the layered contributions of the film’s offscreen partnerships are what made Harry and Sally’s effortless dynamic possible and helped this film to set the gold standard for countless comedies to come.
To even get this film off the ground, Ephron and Reiner channeled their working relationship with one another into that of the film’s main characters. In attempting to answer a central question — can men and women ever be just friends? — the two picked each other’s brains in a long series of interviews and dinners, culminating in Ephron’s penning of the script. From these conversations, she based Harry’s glum, cynical thoughts about relationships on Reiner, and incorporated her own, more optimistic responses into Sally’s dialogue. Both women in this scenario may or may not have also been very particular when ordering food.
This kind of partnership between a screenwriter and director was (and remains) quite novel. As Ephron herself explains in her introduction to the film’s published script, “Movies generally start out belonging to the writer and end up belonging to the director…What normally happens in the course of The Process is that the writer says one thing and the director says another thing, and in the end the most that the writer can hope for is a compromise; what made this movie different was that Rob had a character who could say whatever he believed, and if I disagreed, I had Sally say so for me.”
Ephron and Reiner’s debate certainly covers some antiquated ideas about gender; yes, of course, men and women can be friends, and to say otherwise feels reductive. But the relationship that emerged from their debate, both on and off screen, also comes to transcend that question. Really, Ephron and Reiner’s argument was always about the banter itself, about Harry and Sally’s (and their own) willingness to continually engage with one another despite their differences. As Ephron herself remarked, they didn’t always have to compromise; the comedy came out of the argument, the unlikely partnership, itself.
To that idea, Crystal and Ryan were also an unlikely duo. When Harry Met Sally marked Ryan’s first leading role in any film, let alone in a comedy; her previous parts were more drama-focused, especially given her presence on the daytime series As the World Turns. And while Crystal was already an established comedic actor on television and had previously appeared in supporting roles in other Reiner films including The Princess Bride and This is Spinal Tap, he had also never starred as a leading man in a rom-com before. Reiner notably hesitated before casting him; he didn’t want to jeopardize his close friendship with the actor by having Crystal play a character modeled so closely on himself.
And yet this pair still ended up meshing perfectly. As Crystal remarked of Ryan’s casting, “It was like in a ’40s movie when someone says, ‘And then she walked in!’” Out of their collaboration, both actors came to make important contributions to Harry and Sally’s constant banter; Crystal improvised the funny-talking scene in The Met, for example, and you can see Ryan rolling with the punches with a quick glance off-screen to Reiner.
And then there’s the film’s most famous scene with the fake orgasm in Katz’s Deli. Here, Ryan suggested the setup (being the orgasm itself), and Crystal suggested the punchline (you know the one). In both scenarios, Crystal and Ryan continually display a willingness to play along with one another, bringing the comedic chops that made their characters’ friendship and romance that much more believable.
Both Ephron and Reiner’s and Crystal and Ryan’s creative partnerships are what make Harry and Sally so charming to watch. From the couple’s contentious opening road trip to their fated New Year’s confession, the comedic give-and-take of their respective creators becomes the bedrock of Harry and Sally’s relationship. It’s just heartening to see these characters engage in what is, essentially, doing an ongoing series of bits with your best friend for shits and giggles; here’s this unlikely pair, singing karaoke to “The Surrey with the Fringe on Top” at The Sharper Image, being terrible at Pictionary, and trying to figure out just what the lyrics to “Auld Lang Syne” even mean. The will-they-or-won’t-they sexual tension is simply an added bonus.
This charming relationship set a standard for many genre entries to come. For one, When Harry Met Sally popularized some tropes as far as rom-com pairs are concerned – from the eternal optimist/pessimist dynamic to a confession of love after a sprint through Manhattan streets. Harry and Sally’s rapport also endured in comedies throughout the ’90s and beyond; sitcoms like Seinfeld and Friends hinged on the central question that initially drove Ephron and Reiner, and Ephron herself would bring more bantering opposites to the screen alongside Ryan, especially with You’ve Got Mail.
But above all, it’s Harry and Sally’s own easy chemistry that still makes for a delightful viewing experience to this day. The casual, yet close friendship that grows between them, and the creative partnerships that made that relationship possible, makes for memorable moments of humor throughout When Harry Met Sally that endure 30 years later. And when you find a film with such a perfect balance of humor and heart, you want to get it started as soon as possible.