When Harry Met Sally (1989) – Rob Reiner

The first recommendation from the Great Movies – 100 Years of Film following my screening of Pretty Woman for the romance and melodrama chapter of the book is one of my favourite rom-coms of all time. And personally I think it should have been the main title over Pretty Woman.

Set over the course of a number of years, the story follows Harry (Billy Crystal) and Sally (Meg Ryan) over a course of a number of encounters that sees them hating one another, falling in love, hating one another, becoming friends, and no surprise considering the category, falling in love at the end of the film.

Written by Nora Ephron, who in the late 80s and 90s seemed to be the master of the romantic comedy, the story is set against the backdrop of New York City and features musical numbers by Harry Connick jr.

Featuring a supporting cast that includes Carrie Fisher and Bruno Kirby the film, even now is consistently funny, and heart-touching as Harry and Sally debate the eternal question of whether or not men and women can just be friends.

The pairing of Crystal and Ryan is excellent, though I feel her chemistry with Tom Hanks is even better. Watching the story unfurl, intercut with the stories of other couples and how they found one another, is enough to inspire even the most stoic of romantics.


This film has been part of my life since it was first released, and is often revisited on New Year’s Eve, when the climax of the film takes place, and often makes a nice pairing with Casablanca.

The dialogue is pitch-perfect, and has been endlessly quotable in my own life, often finding just the right moment to make an appearance. I love it, and will continue to do so through the coming years.

I love watching Crystal and Ryan interact, and they way their relationship blossoms and changes, realistically, through the course of the film. There are mistakes that both parties make, even as they face their own fears and worries about the people they care for.

Besides The Blues Brothers, this was a movie that I saw Carrie Fisher as more than just my Princess, I saw her as a comedic actor, and a talented performer. Makes me miss her all the more.

With Reiner’s able hand, who already had a number of successes under his belt, including This is Spinal Tap and The Princess Bride, Nora Ephron’s brilliant script, wonderful turns by Crystal and Ryan, the beauty of New York City, and classic songs interpreted by Connick jr., this one can’t help but entertain, and win the heart.

And it’s still amazingly better than Pretty Woman.


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