Billy Crystal Reflects on Iconic Moments from ‘When Harry Met Sally…’
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In an exclusive cover story for PEOPLE magazine, renowned actor Billy Crystal revisits his experience filming the beloved romantic comedy *When Harry Met Sally…*, a classic that has endured since its release in 1989. Speaking fondly of his collaboration with director Rob Reiner and costar Meg Ryan, Crystal shares insights into how several memorable scenes came about, shedding light on the creative processes behind the film.
Crystal, now 78, looks back on the making of the film in the context of Reiner’s personal struggles, recalling how the director was navigating a difficult divorce from Penny Marshall during the project’s production. “Rob was really going through some tough times,” Crystal explained. “We would be on the phone constantly at night.” This constant communication between them fostered an environment ripe for collaboration.
Familiar moments from the film were indeed born from their friendship. One such scene features the two protagonists, Harry Burns, played by Crystal, and Sally Albright, portrayed by Ryan, sharing a tender moment while watching *Casablanca* on the phone. Crystal shared, “That was stuff we did. It’s one of my favourite little exchanges. That was pure us.”
Drawing on his background in comedy, Crystal also incorporated elements from his personal experiences into the film. He revealed that an original sketch he had written earlier about two men discussing therapy led to the development of a memorable scene where he converses about divorce with the late Bruno Kirby while at a football game. The comic timing was enhanced by interruptions from enthusiastic fans doing “the wave,” adding an unexpected layer of humour. “We put that in and it’s a terrific scene,” Crystal stated confidently.
No discussion of *When Harry Met Sally…* would be complete without addressing the iconic restaurant scene where Ryan’s character pretends to have an orgasm. This pivotal moment, which continues to resonate with audiences, stemmed from a conversation between Crystal and screenwriter Nora Ephron. “Nora had this idea that we should talk about the fact that women fake orgasms,” he recalled, noting that Ryan suggested the idea of staging the incident in a public setting. The result was a scene that became legendary, further immortalised by an unforgettable punchline delivered by Reiner’s mother, Estelle. “That one was a dream to do,” Crystal reflected.
Over the years, *When Harry Met Sally…* has gained recognition not just as a fan favourite but also for its cultural significance. In 2022, the film was inducted into the National Film Registry by the Library of Congress, earning its place as a work deemed “culturally, historically, or aesthetically significant.”
Tragically, Reiner passed away on December 14, 2025, along with his wife Michele, under circumstances that shocked many. Their son, Nick Reiner, was subsequently arrested and charged with two counts of first-degree murder, though he has pleaded not guilty. This heartbreaking turn of events adds a layer of sadness as Crystal reminisces about the joyful collaboration he shared with his late friend.
In the midst of reflecting on the past, Crystal is also looking to the future. His one-man show, titled *860*, launches on October 21 at Broadway’s Imperial Theatre, running for a limited engagement of 14 weeks. The show will delve into his personal experiences, including a devastating loss—his home of 46 years during the Pacific Palisades fires of 2025.
Despite the tumultuous events of the past year, which Crystal describes as “the worst year of his life,” he remains committed to spreading joy through his craft. “Laughter made my life possible,” he asserts, highlighting the role humour plays in his life and performances.
As Crystal continues to navigate these challenging times, the legacy of *When Harry Met Sally…* and the friendships forged during its production remain a source of comfort and inspiration. He aims to channel the laughter and joy from those cherished memories into his upcoming performances, ensuring that the spirit of comedy endures.