It seems to me that since the Sixties, truly great romantic comedies have been few and far between. Aside from the films of Woody Allen, I can only think of two off the top of my head. One is rather recent--Down With Love from 2003. The other is from all the way back in 1989. When Harry Met Sally has numbered among my favourite films ever since I first saw it.
If When Harry Met Sally is one of the truly great romantic comedies, much of it is due to Nora Ephron's screenplay. Ephron created two charming characters in Harry and Sally, each saddled with his or her own neuroses. Indeed, the progression of their relationship from acquaintances who can barely tolerate to each other to best friends to soul mates may well be one of the most realistic portrayals of a relationship on film. What is more is that the film also features some of the wittiest and sharpest dialogue of any film in recent memory.
Of course, Nora Ephron's script would have been worthless without a cast to breathe life into her characters. Billy Crystal and Meg Ryan make Harry and Sally flawed, yet charming and loveable (indeed, I think if my mother had her way, I would have married Meg Ryan...). Their performances are very subtle, with both conveying emotions with a single glance or gesture. Kudos must also go to the supporting cast. Bruno Kirby as Harry's friend Jess and Carrie Fisher as Sally's friend Marie are wonderful.
I must also point out that When Harry Met Sally is definitely a movie for movie buffs. There are a number of references to classic films throughout the movie. Indeed, movies figure prominently in the lives of Harry and Sally. They share a love for Casablanca. When Harry is mourning the loss of Sally, at one point he has It's a Wonderful Life on the telly. And there are references to The Lady Vanishes, Pillow Talk, Planet of the Apes, Annie Hall, and other films. Even the climax, on New Year's Eve, is remniscent of The Apartment (perhaps the greatest romantic comedy of all time).
When Harry Met Sally centres around the truly simple question of whether men and women can ever truly be friends without sex getting in the way. It must be pointed out, however, that it never truly answers this question. Harry and Sally do become friends, but it seems clear to me that they were in love almost from the beginning. Indeed, after seeing Sally at an airport for the first time in five years, Harry goes out of his way to talk to her. Even once their friendship commences, it is clear that they are something other than friends--in everything from the way they look at each other to the way they speak to each other. When Sally gets angry at Harry after they have sex for the first time, I suspect it is not because she thinks he took advantage of her, but rather because she was forced to confront the feelings they had both repressed for so long. Quite simply, When Harry Met Sally fails to answer the question of whether men and women can be friends simply because Harry and Sally were in love all along. That having been said, it does point out something very important. At the root of every successful romantic relationship there must be friendship. Every relationship Harry and Sally have fail, until they finally get together. In real life, I fear all too often people forget that to be lovers, they must be friends as well if the relationship is to succeed. Too often I think they are blinded by mere physical appearance or other unimportant matters. Given that, I think it is perhaps little wonder it took Harry and Sally a while to finally get together....
For me this is one of the reasons When Harry Met Sally is so great. It does not create a simple boy meet girl plotline with all the traditionally romantic elements plugged in. Instead, it presents us with a realistic relationship in which two friends sadly will not admit how they truly feel about each other until years have passed. That they do finaly get together perhaps is hope for romantics everywhere.