Billy Crystal is looking back on the personal moments and creative conversations that helped shape When Harry Met Sally.
The 1989 romantic comedy paired Crystal with Meg Ryan, directed by his longtime friend Rob Reiner. Speaking with PEOPLE nearly 11 months after Reiner’s death, Crystal revealed the origins of three scenes that became fan favorites.
Crystal explained that Reiner was navigating his divorce from Penny Marshall while the movie was being made. The close friends frequently spoke on the phone at night as Reiner worked through the difficult period.
Those conversations directly inspired a sequence in which Harry and Sally watch Casablanca from their separate homes while talking on the phone.
“That was stuff we did,” Crystal said. “It’s one of my favorite little exchanges. That was pure us.”
Another memorable scene finds Harry discussing divorce with Bruno Kirby’s character, Jess, during a football game. Each time the men begin opening up about their feelings, spectators interrupt by standing to perform the wave.
Crystal said the moment grew out of an original comedy sketch he had written about two men discussing therapy. Reiner repeatedly brought up the concept, and the pair eventually developed it into the stadium sequence.
“We put that in, and it’s a terrific scene,” Crystal said.
The movie’s most famous scene, set inside Katz’s Delicatessen, came from a larger collaboration among Crystal, Ryan, Reiner and screenwriter Nora Ephron.
Ephron wanted Harry and Sally to discuss women faking orgasms because Harry considered himself an experienced and desirable partner.
The collaborators then devised the reaction from an older customer, who responds by telling her server, “I’ll have what she’s having.” Reiner cast his mother, Estelle Reiner, to deliver the now-iconic line.
“That one was a dream to do,” Crystal recalled.
More than three decades later, When Harry Met Sally remains a romantic-comedy favorite; the Library of Congress selected the movie for preservation in the National Film Registry in 2022 because of its cultural, historical, and aesthetic significance.
Crystal will next take the stage in his autobiographical one-person Broadway production 860. The limited engagement opens Oct. 21 at the Imperial Theatre and runs through Jan. 3. The production explores how Crystal and his wife, Janice, endured losing their home of 46 years in the 2025 Pacific Palisades fires.
