Rob Reiner watches Harry Connick Jr. sing the sound track to When Harry Met Sally.Hulton Archive/Getty Images
Reiner, who had recently divorced from his first wife, Penny Marshall, and was rather pessimistic about relationships in general, had approached Ephron with the initial idea for the film. She was hesitant, but in Reiner, she found her inspiration for Harry.
“Rob is a very strange person,” she wrote in the introduction to the script. “He is extremely funny, but he is also extremely depressed—or at least he was at the time; he talked constantly about how depressed he was.”
It’s an off-putting but also an endearing cocktail of traits that Ephron captures to perfection in Harry, who delivers the darkest jokes you’ve ever heard without batting an eye. Things like, “When I buy a new book, I read the last page first. That way, in case I die before I finish, I know how it ends. That, my friend, is a dark side” or “They should put the two sections together, real estate and obituaries. ‘Mr. Klein died today leaving a wife, two children, and a spacious three-bedroom apartment with a wood-burning fireplace.’”
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