When Harry Met Sally: A Movie That Made A Generation

I’ll be honest, even though it’s one of the most popular movies of all time, I never got around to seeing it until late last year.

I know, I know, all anyone has to do is say: “I’ll have what she’s having” and instantly 99.9% of the planet knows what they’re talking about, but somehow a guy like me (who could have a conversation with you exclusively in movie quotes if he tried) never got around to seeing it.

When I finally did, it quickly became one of my favourites. The quick-witted dialogue, the beyond charming supportive cast and of course Billy Crystal and Meg Ryan are all incredible, but it was one of the smartest movies I’ve ever seen.

After I watched it I quickly got my hands on the script and read through it a couple of times and I realized why I loved it so much: The movie writes its own rule book.

Director Rob Reiner does away with just about every convention and trope in the book. Acting more like an essay, rather than a conventional movie, it asks its audience right off the bat if they think men and women can be friends. We then follow the pair as they try and figure this out for themselves. And that’s it.

There’s no contrived “Honey, my job’s moving me to Paris …” the two don’t get caught in a situation where it looks like one of them is cheating; there’s no forced external conflict, instead every argument, every conversation, every plot turn, it all comes from Harry and Sally’s personalities and insecurities.

In many ways, the movie beat Seinfeld to the punch. Without paying much attention When Harry Met Sally is just a couple of people talking about “nothing” for an hour and a half … but really it’s sneakily getting you to think about the taboo topics in a blunt and candid way.

The candor and honesty of the film works because it was based on Reiner and writer Nora Ephron’s friendship. Everything from watching movies over the phone, to Harry’s line:

“When I buy a new book, I always read the last page first, that way in case I die before I finish, I know how it ends. That, my friend, is a dark side.” are all taken directly from the creative duo’s lives.

“All I can ever do is I look into myself and try to figure out, how do I think as a man? There are certain universal things that men experience and the fact that I was working with Nora Ephron, she brought the female perspective to the mix, and we made it a part of the creative process to say what actually happens between men and women. You know, it’s not about the cute meet or putting some obstacles between the lovers so that they get together, but what actually happens with men and women.” – Rob Reiner (Q&A With the AP)

Look, I don’t think I’m making that bold of a statement when I say When Harry Met Sally is one of the smartest scripts ever written. It’s not out to force an opinion down your throat or make you argue about whether or not “we were on a break”, it just lets you live in the shoes of a couple of people for a while.

At the end of the day isn’t that the job of a good movie? To let you experience a problem from someone else’s perspective while being as honest as it can. It’s a movie that’s influenced everything that’s come after it, coined the term “high maintenance/low maintenance” and gave us the most unforgettable diner scene of all time. It’s an innovative film that changed the game and definitely deserves your next watch.


  • While a great many would see him as a hero, there are some that would prefer the term vigilante. Gregory is an aspiring filmmaker who loves writing, directing, coffee and long walks on the beach.


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