Director: Rob Reiner
Writer: Nora Ephron
Stars: Meg Ryan, Billy Crystal, Bruno Kirby, Carrie Fisher
Synopsis: Harry and Sally have known each other for years, and are very good friends, but they fear sex would ruin the friendship.
There has been much debate over the past few decades regarding Meg Ryan’s greatest work in the romantic comedy sector of cinema. The answer is definitive. It is, and always has been, When Harry Met Sally. Not only is it Meg Ryan’s best romantic comedy, but it’s the greatest work in the genre of all time. It’s the perfect storm of cast and crew finding each other at the right time and establishing chemistry and rhythm that has since been unmatched.

There’s no better place to start with this film than the script, the backbone of the movie that keeps things moving. This is only the third script of Nora Ephron’s that crossed the finish line of being released, with the prior two being directed by Mike Nichols. This script is funny and witty, and every scene has a purpose. Nothing should be cut out and it makes the most of every second. When Harry Met Sally doesn’t fall into the trap of other similar films, particularly modern romantic comedies, that overload their story with extraneous scenes that increase the runtime way past what is necessary. Something especially notable about Ephron’s work here is that even though there are a plethora of amazingly quotable one-liners, they are all part of the dialogue between the characters and not just used to get a laugh at the end of a scene. Both Harry and Sally are written well and fleshed out to where just a couple of interactions with them tell us exactly who they are. It takes massive writing chops to pull that off so quickly.

While Nora Ephron went on to direct her work for most of the rest of her career, it took six scripts to get there. After consecutive collaborations with Mike Nichols, Ephron hands the reins of When Harry Met Sally over to Rob Reiner amid a historic stretch. Between 1986 and 1992, Reiner directed Stand By Me, The Princess Bride, When Harry Met Sally, Misery, and A Few Good Men. Talk about an all-time run. Reiner is at the top of his game here, allowing his straightforward style to let the script work its magic and the actors run with it. In addition to Reiner’s direction, future director Barry Sonnenfeld is behind the camera here offering his cinematic eye. The two of them capture the beauty of New York City in fall and winter in their unique way, letting the colors and sights speak for themselves without extra flare and flash. Every time Harry and Sally are walking through parts of the city I can’t help but think this era was the best time to ever live in the Big Apple and anyone there now is just chasing a life that will never exist again.
The behind-the-camera work sets the stage for the real stars of the show, Billy Crystal and Meg Ryan. Both Harry Burns and Sally Albright are played and written so perfectly that films have been chasing variations of their characters for decades since the film’s release. Each of them has their ways of living that they stick to, Harry with his rules of relationships and Sally with knowing specifically what she wants and how things should be done. Their chemistry together is truly singular in the genre, as it’s more than just pure physical attraction. There’s a deep connection between them, once they each let the other one in a little bit. For a while in the film, they exhibit what true friendship can be like, regardless of gender. Of course, the story must take them to the romantic pit, but their relationship still exhibits a level of closeness that is hard to achieve in any relationship. With no disrespect to one Tom Hanks, Billy Crystal has unquestionably the best chemistry and is the greatest scene partner that Meg Ryan has ever had. Their dialogue flows and bounces off one another so naturally. Carrie Fisher and Bruno Kirby also turn in great performances as Harry and Sally’s best friends, and the four of them engage in the most electric landline telephone conversation ever committed to film. It’s well known now that they had to actually all be on the phone together to pull this off, and the scene is so much better for it.

The impact of When Harry Met Sally is impossible to understate. The writing, direction, and acting are unimpeachable and the combined efforts of all involved helped bring the world into the modern era of the romantic comedy. Individually, great things come for almost everyone after this film but the greatness found here will never be replicated. Try as you might, it can’t be done. It’s a perfect movie, the pinnacle of Meg Ryan’s career, and the only thing I think about when thinking about Billy Crystal.