When Harry Met Sally is the greatest rom-com ever made. It’s the product of the galacticos of the cute, talky, adult comedy: Nora Ephron, Rob Reiner, Meg Ryan, Billy Crystal, and Carrie Fisher, all at the peak of their powers. It’s set in the perfect place and at the perfect time: a bourgeois corner of New York City in the 1980s, when men wore sweaters and women wore hats. You couldn’t ask for better building blocks.
But that’s not what makes it great. A majority of romantic comedies set their focus on the beginning of a relationship: the exciting part. The thesis of When Harry Met Sally is that love is not about the spark, but about how you feel years down the line. And somehow, over the course of just 95 minutes, we get to see a relationship develop over the course of 12 years. Even considering that there are basically only four characters in the movie, it’s an astonishing bit of writing and acting to establish two leads who just get each other so completely. It’s the rom-com every filmmaker should aspire to make, and the romance every couple should aspire to have.
Without Julia Roberts, Pretty Woman isn’t second on this list. Without Julia Roberts, Pretty Woman probably isn’t even on this list. The premise of Pretty Woman is sticky, and there’s a lot more messiness to the conceit, to the plot, to the Jason Alexander of it all to contend with than your average meet-cute. The romance, and especially the comedy of this movie, lives and dies on the charisma of its heroine. And in 1990, no one was more charismatic than a fresh-out-of-the-gate Roberts singing Prince in the bathtub. Sure, some folks had discovered her in Mystic Pizza, but for most, Roberts was a revelation in Pretty Woman.
Two permits do not equal a license, but inspired casting, some of the best one-liners in cinematic history, and a boatload of yellow plaid equals a genre-defining ‘90s teen movie. Amy Heckerling’s adaptation of Jane Austen’s Emma via Beverly Hills is more com than rom, but its climax takes place when the ditzy but deep Cher Horowitz realizes that she is “totally butt crazy in love with Josh,” her ex-step-brother, played by a young Paul Rudd.
Sleepless in Seattle’s genius is distilled in one of its simplest scenes: A bathrobe-clad Annie Reed (Meg Ryan) settles into her pink kitchen, using a knife to remove the skin from an apple in one continuous band as she listens to talk radio. The camera closes in on her face as the voice of widower Sam Baldwin (Tom Hanks) describes the magic of meeting his late wife, and she begins to weep. In Annie’s face is a deep longing, the restlessness of someone who wants more than Mr. Perfectly Fine but feels absolutely ridiculous for it. Meanwhile, 2,764 miles across the country, Sam comforts his son by offering a single detail to remember his mom by: “She could peel an apple in one long curly strip,” he tells him. “The whole apple.”
Little coincidental glimmers like these tether Annie and Sam for most of Nora Ephron’s perfect 1993 rom-com, as the two of them live out their own pretty OK relationships while longing for that fabled and elusive spark. It’s only in the 11th hour, after many plane rides and several leaps of faith, that they find it in each other atop the Empire State Building. Witty banter, a stacked cast, and dreamy scenery aside, this is one of those rare, hopeful stories that makes heroes out of romantics, suggesting no obstacle is too great for even the slimmest chance at the real thing.