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?”