Classic Movie Review: 'When Harry Met Sally'

The classic on this week’s Everyone is a Critic podcast is When Harry Met Sally, director Rob Reiner’s 1989 romantic comedy that arguably set the template for every romantic comedy that came after it. Reiner, whose The Princess Bride turns 30 this weekend and inspired our podcast to focus on Reiner’s work, directed When Harry Met Sally from a script by Nora Ephron who would go on to take the mantel of the leading voice in romantic comedies in Hollywood throughout the 90’s and early 2000’s.

The template is thus, two people who seem ill-suited for each other get repeatedly thrust together by fate before sleeping together, montage together and then break-up, montage, and finally have a romantic reunion. These movies could write themselves after a while but in fairness to Reiner, when he conceived of When Harry Met Sally, the template wasn’t quite so set in stone. In fact, in pairing the comic Billy Crystal with the actress Meg Ryan, Reiner found something that still feels very fresh in their unusual chemistry.

Harry (Crystal) and Sally (Meg Ryan) met at the University of Chicago in 1978. Sally happened to be headed to New York to take a job as a journalist and Harry headed the same way for work offered to help pay for the trip and share the driving. They immediately don’t get along as Harry launches into his off-putting diatribe about how men and women can’t be friends because sex always gets in the way. Sally, put off by Harry’s blunt talk about how all men want to sleep with her, goes quiet and the two part ways seemingly to never see each other again.

Five years later, on a plane, Harry and Sally reconnect. Sally is in a new relationship while Harry has an even bigger surprise, he’s getting married. That doesn’t stop him from flirting with Sally and even asking her to dinner when they get to their destination. She says no and once again they part. Finally, we cut to another five years later, both Sally and Harry are fresh out of relationships with Harry still stinging from a recent divorce. In a speech that remains remarkable to this day, Harry lays out the scene of the break up to his pal played by Bruno Kirby. The brutal honesty and dark humor of the story is magnificent and Crystal demonstrates the kind of acting chops that few other movies have ever allowed him to show. Crystal is a consummate performer and given a brilliant monologue to deliver he becomes a magnetic presence.

When Harry spies Sally at a bookstore he immediately sidles up to her and begins a conversation that seems as if it just picked up from the last time they saw each other. The conversation turns into lunch and a long walk and blossoms quickly into exactly the friendship Harry said was not possible. They stay up late talking on the phone, watch movies together, go to lunch and become such a presence in each other’s lives that everything else feels secondary, including the romantic entanglements that they engage in and talk to each other about.

These conversations between Harry and Sally are pure magic. Reiner and Ephron give their two leads so much to work with and then it’s just taking advantage of the New York scenery. As much I believe the delivery and chemistry of Crystal and Ryan sparkles, we cannot underestimate the words given to them by Ephron who, even at her most trite in her late 90’s romantic rehashes, could string together terrific banter. The banter in When Harry Met Sally is so fluid and so natural and yet completely comic. Harry and Sally are just naturally funny together.

Billy Crystal has never been given credit as a proper leading man. Always written off as too short or two schticky, Crystal shows throughout When Harry Met Sally that sometimes being handsome is as much about wit as it is about being tall and muscled. The confidence of Harry, the wit, he makes Sally smile and that smile is every bit as much a turn on as being the tallest guy in the room. Wit and smarts sometimes are more fun than a guy who can pick you with one arm and carry you to the bedroom.

When Harry Met Sally is witty, romantic, and smart. The film is populated by wonderful characters and wonderful moments. It’s so good that even the ending with its admittedly rather forced monologue from Harry that’s just a little too perfect, still manages to land. Crystal’s magnetism in that moment as he finally lays his heart bare is just so damn winning that the too perfect nature of the speech still works. Don’t misunderstand, it’s an incredibly romantic speech, one that he should be proud to have delivered, it’s just a little forced into the ending and a little too perfect.

When Harry Met Sally is underestimated today for several reasons. First is the fact that Meg Ryan went on to do two movies with Tom Hanks that established them as the first couple of romantic comedy. The second is just plain time. Time has rendered When Harry Met Sally as just another romantic comedy. Every movie after When Harry Met Sally, especially Nora Ephron’s hit movies, kept rehashing Harry and Sally and slowly made When Harry Met Sally seem ordinary and simply of a genre rather than that genres progenitor.

That’s a shame because if you can put aside how watered down and formulaic the romantic comedy has become since When Harry Met Sally debuted in 1989, When Harry Met Sally is exceptional. This film set the tone for all romantic comedies to come after it because it is just that damn romantic, smart and funny. This film has all of the tools and all of them are sharp, witty and wonderful. Crystal and Ryan’s chemistry, I would argue, is actually better than her chemistry with Tom Hanks in Sleepless in Seattle and You’ve Got Mail. Hanks however, was a respected actor while Crystal was written off as just a comic.

Crystal didn’t do himself any favors by choosing terrible comedies after When Harry Met Sally, movies that played off of terribly gimmicky premises, and played to his worst instincts as a comic. It was as if Crystal bought into all of the criticisms about him that he wasn’t handsome enough to be a leading man or he wasn’t believable enough as a romantic ideal. It’s a shame because he could have made more movies like When Harry Met Sally and created even more iconic moments to match those two incredible Harry monologues in When Harry Met Sally.