We all have our own favorite romantic comedy. There’s simply been too many great ones to universally agree on one. That being said, there are a few classics that really need to appear somewhere on any competent "Best Of" list. When Harry Met Sally is one of those. Interestingly, however, it turns out a ton of the film’s most classic scenes and lines were actually written out of heartbreak and straight up platonic friendship.
Nora Ephron wrote When Harry Met Sally, but prior to the film getting remade, it was collaboratively re-written by Ephron, director Rob Reiner and lead actor Billy Crystal. At the time, Reiner’s marriage to the legendary Penny Marshall was failing, and he and Crystal hung out and talked on the phone constantly to help him cope. During that bonding time, many of the film’s most touching exchanges between Harry and Sally happened for real... between Rob and Billy.
Here's what Crystal had to say during an interview with Entertainment Weekly...
He’d call me, he was all alone, you know, I’m happily married — with another kind of magic and two kids — and the phone rings and it would be him. "Channel 9, are you watching?" And then I’d put it on: "Oh, my God, what is this?" And it was arena football or something. And, "What is this? Indoor football? What’s next? Arena golf, arena jogging?" So we’d just play around, and then we’d just channel surf, and that became the split screen talking about Casablanca. And also the symptomatic headaches of depression, you know, "It’s a 24-hour tumor, they’re going around," is something I actually said to him. And he said, because I was having migraines, and he said, "Go to the doctor." It’s a line in the movie, "No, he’ll just tell me it’s nothing."
At first, Reiner was reportedly less than excited about the idea of letting Crystal basically write his own personality into newer drafts of the script, but after some back-and-forths, he decided to let the actor get personal and more importantly, to let him include all of these items and conversations that were plucked straight from their lives. That decision, along with the casting of Meg Ryan, helped to turn what could have been a marginal romantic comedy into movie magic.
Humorously enough, that Ryan casting took a little more luck than you might think. The starlet read alongside Billy Crystal for Throw Mama From The Train the year before, and Crystal fell in love with her immediately. In fact, he reportedly begged director Danny DeVito to cast her, but he ultimately decided go with someone older. To this day, Crystal wonders what may have happened if she was cast in the first film. Would Rob Reiner have been okay with still putting her in When Harry Met Sally? We’ll never know.