Secrets of the Classic Film ‘When Harry Met Sally’ Revealed

When the stars and director of When Harry Met Sally … sat down to celebrate the movie’s 30th anniversary at the TCM Classic
Film Festival in Los Angeles, it was like no time had passed.

“We reconnected exactly the way we did when we were making the movie,” says Rob Reiner of the film’s costars Billy Crystal and Meg Ryan. “The rhythms were all there — it was great.” That spark was evident from the moment Meg, 57, walked into the room to audition with Billy, 71, for the part of his platonic friend-turned-love interest. “You always look for chemistry, and it was right there from the beginning,” the movie’s director recalls. “They started reading, and in the first 10 seconds, I said, ‘This is it!’”

For Meg, who had played supporting roles in films like Top Gun, landing the lead was a big break. “They took an enormous chance with me,” she says. “It was the kind of music Billy, Rob and I knew how to play together.”

The film’s central question — can a man and woman be friends without sex getting in the way? — was inspired by Rob’s real life. He’d gotten divorced from his first wife, the late Penny Marshall, nearly a decade before the film was made. “I was in and out of disastrous relationships and making a mess of my dating life, and I said, ‘There’s got to be a movie in here somewhere,’” he remembers. Enter Nora Ephron, who penned the film’s Oscar-nominated screenplay.

“She was a journalist, and she started interviewing me,” The Princess Bride director says. “Then I interviewed her, and Harry
became an extension of me, and Sally became an extension of her. And we lucked out like crazy with [Billy and Meg].” Over the course of two weeks of rehearsals, the script evolved.

“We all sat in Rob’s office for hours and hours just talking about it,” the Sleepless in Seattle actress says. Notes Billy, “You had Nora and Meg and [co-star] Carrie [Fisher] throwing everything in together, and that’s why I think it’s such a powerful screenplay.” This all-hands-on-deck approach continued once shooting began. A complicated scene in which Meg and Carrie have a phone conversation at the same time Billy is on a call with his best friend (played by Bruno Kirby) seemingly took forever to get right.

“It was take 56 or 57, and the sound guy said, ‘No good. There’s a bird. Do it again,’ ” the comedian said, adding jokingly, “We had to kill the bird. When Harry Killed Birdie!” For the classic scene in which Meg shows Billy how she can fake sexual pleasure in the middle of Katz’s Deli, Rob demonstrated how to play it in front of the entire cast and crew. That included Estelle Reiner, his mom, who delivered the line, “I’ll have what she’s having” (which was Billy’s idea!).

“I had an orgasm in front of my mother,” Rob deadpans. Concurs Billy, “He had an orgasm Mighty Joe Young would be proud of.”

But it all worked out well in the end, both on and offscreen. In the original script, Harry and Sally didn’t wind up together, but
that changed to reflect Rob’s real life. While shooting the movie, “I met the woman I’ve now been married to for 30 years,” Rob says of wife Michele Singer.

Now that’s what we’d call a Hollywood ending.

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