During the filming of When Harry Met Sally... in 1989, Billy Crystal and Meg Ryan developed a unique creative partnership that redefined the modern romantic comedy. Their collaboration, supported by director Rob Reiner and screenwriter Nora Ephron, produced some of the most enduring behind-the-scenes stories in film history.
The famous “fake orgasm” scene at Katz’s Delicatessen was Ryan’s idea to prove Harry’s cynicism wrong. Crystal then added the punchline, “I’ll have what she’s having,” which was delivered by Reiner’s mother, Estelle. To capture Harry’s post-divorce loneliness, Crystal stayed in a separate hotel room from the rest of the cast and crew while shooting in Manhattan. Many scenes were based on the real friendship between Reiner and Crystal. For example, the split-screen telephone conversations where they watched the same TV shows were activities they actually did together every night.
The script originally ended with Harry and Sally parting as friends. However, Reiner met his future wife during production and decided a romantic reconciliation was more fitting. Reiner encouraged Crystal and Ryan to spend time together off-set to build a genuine rapport, ensuring their on-screen rhythm felt effortless.
Columbia Pictures released When Harry Met Sally in selected cities, letting word of mouth generate interest, before gradually expanding distribution. The film grossed $92.8 million in North America, and was released to critical acclaim. Ephron received the BAFTA Award for Best Original Screenplay, as well as nominations for the Academy Award, WGA Award and Golden Globe. The film is ranked 23rd on AFI’s 100 Years... 100 Laughs list of the top comedy films in American cinema and number 60 on Bravo’s “100 Funniest Movies.”
In early 2025, Crystal and Ryan reunited at Katz’s Delicatessen to recreate the iconic diner scene for a Hellmann’s Super Bowl commercial. This reunion marked 35 years since the film's release, with the actors even wearing outfits that paid homage to their original 1989 looks.
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