Of all the modern day romantic comedies, few are written as confidently as Nora Ephron's "When Harry Met Sally…" The story is deceptively simple, yet devastatingly witty — and that has as much to do with Ephron's crackling grasp on syntax as it does with the conversations that inspired her. Ephron was notorious for taking inspiration from everything around her in her work. For "When Harry Met Sally," she was partly inspired by interviews (and heated debates) with actor-slash-director Rob Reiner. He provided the template for one half of the film's titular duo, the cynical, recently-divorced Harry Burns. Sally was, of course, inspired by Ephron herself. Their dynamic (or at least the dramatization of it) built up fascinating stakes in a story where nothing "really" happens. Writing it had been easy enough, but finding two actors that could carry the weight of it would prove slightly challenging.

Casting the role of Sally was a breeze, according to Scott Meslow's "From Hollywood with Love: The Rise and Fall (and Rise Again) of the Romantic Comedy." Meg Ryan was one of the first actors to read for Sally, and Reiner knew she was the one right away. "Meg was literally the second actress that came in," casting director Jane Jenkins recalled. "She left the room, and Rob said: 'It's her part. Cancel everything else.'" Casting her counterpart could have been similarly simple: By all accounts, the role was pretty much made for Billy Crystal. But Reiner was hesitant to cast him in spite of that.

The Easy Choice Was Also The Right Choice

Getting the casting right for "When Harry Met Sally" was a pretty serious task for Rob Reiner. "Rob always said it's the kind of movie that has a very high degree of difficulty in that it has no safety net," Nora Ephron explained. "It entirely depends on your caring about those two people." Audiences had to root for Sally and all her neuroticism as much as they did Harry, despite his casual chauvinism. That meant casting an actor who could deliver Harry's most callous remarks with some degree of geniality — or, barring that, naïveté. Harry was, after all, molded after Reiner, a man who seems impossible to dislike. Who better to embody all that than Billy Crystal, who'd been Reiner's closest friend since 1975?

The writing was on the wall for everyone but Reiner: He feared what working on the project might do to their decade-long friendship. Ironically though, overlooking Crystal might have made an equal dent in their relationship, as the actor was well aware of the snub. "I knew from agents and managers that he had met with almost every male actor my age, except me," Crystal said. "I was not happy about that, but what could I do?"

'This Is Silly. Let's Go To Billy'

Rob Reiner and Jane Jenkins courted names like Richard Dreyfuss, Michael Keaton, Albert Brooks, and even Tom Hanks (then a few years removed from his breakout role in "Big") for the role of Harry. Yet, time and time again, the conversation around the character kept circling back to Billy Crystal. Eventually, Reiner saw what everyone else already understood: that Crystal was pretty much the only person that could "play" him onscreen.

"Rob finally said, 'Why am I doing this? This is silly. Let's go to Billy,'" Jenkins recalled. Fortunately, there were no hard feelings on Crystal's part, seeing as casting continued without a hitch. The actor's friendship with Reiner notably survived the project, too — in fact, the two are still best friends to this day — but it's kind of nice to know that Reiner was cautious about ruining a good thing unnecessarily.

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