When Billy Crystal Met Sally

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Can a man and a woman just be friends? The question existed long before the feature film When Harry Met Sally… was released in 1989, but director Rob Reiner and screenwriter Nora Ephron turned the debate into one of the most sparkling and popular romantic comedies in movie history thanks to the winning chemistry and irrepressible charm of its two lead performers, Meg Ryan and Billy Crystal.

If it’s been a while since you saw the film, we’ll catch you up. Harry and Sally meet on a long drive from New York to Chicago – during which Harry claims that women and men can never be “just friends.” Over the years, Harry and Sally keep running into each other, claiming to have nothing more than a platonic friendship – until a climactic New Year’s Eve party that threatens (or promises) to upend their assumptions about each other and about love. Carrie Fisher and Bruno Kirby co-star in the film, as “Sally” and “Harry”‘s best friends.

The film is well known for its memorable “faking it” scene, filmed at New York’s famed Katz’s Deli.

Crystal was born March 14, 1948, in New York City. He moved to Long Island with his family while he was a toddler. (His father owned and operated the Commodore Music Store in Manhattan.) After attending Marshall University in West Virginia on a baseball scholarship, Crystal ultimately transferred to New York University, where Oliver Stone and Christopher Guest were among his classmates.

His early success was in television, thanks to his comedic chops and knack for impersonations. One big opportunity was when Norman Lear cast him for a 1976 guest appearance on All in the Family as actor Rob Reiner’s best friend. The two ultimately became real life friends. His breakthrough role was on Soap, where he portrayed a gay character during the series’ 1977-1981 run. In 1982, he was given his own variety show on NBC, The Billy Crystal Comedy Hour, but it was quickly cancelled due to poor ratings. However, in the years to come, his comedy specials on cable proved to be so popular that he became a favorite host for the Academy Awards, which he did nine times, winning multiple Emmys for hosting and writing.

Crystal has a long association with Saturday Night Live, and was in the regular cast for the 1984-85 season, its tenth, reuniting with his NYU classmate, Christopher Guest. (Earlier that year, Crystal had a cameo in Reiner’s This Is Spinal Tap.)

The lifelong sports nut delivered a moving—and funny—eulogy at Muhammad Ali’s funeral service in 2016.

When Harry Met Sally… , with a budget of a reported $16 million, was originally released in early summer 1989 in a few theaters to build word-of-mouth. It did so well, even up against such blockbusters as Batman and Indiana Jones and the Last Crusade, that when the film was given a wide release on July 21, it was embraced by filmgoers. It ultimately earned $92.8 million, good enough to be ranked #11 for the year.

When the film was made, Crystal was 41 years old. The popular actor-comedian would soon score with the two City Slickers movies. Ryan was just 27 and already a film veteran when the movie was released. Four years later, she starred in the 1993 film, Sleepless in Seattle, opposite Tom Hanks.

When When Harry Met Sally… was released, Reiner was 42 and had already directed such classics as This is Spinal Tap, Stand By Me and The Princess Bride.

Crystal was selected for 2023 Kennedy Center Honors, which are given annually for lifetime achievement to the arts. Not long after the event, he was interviewed on CBS Mornings.