“When Harry Met Sally…” premiered in 1989, it became an instant touchstone of the romantic comedy genre.
Directed by Rob Reiner and written by Nora Ephron, the film explored whether men and women can remain just friends over the course of a decade of encounters in New York City.
Its iconic scenes, crisp dialogue, and unforgettable Katz’s Delicatessen moment made Harry Burns and Sally Albright enduring figures in pop culture.
Over three decades later, the principal cast members’ lives and careers reflect a mix of continued creative work, personal achievement, loss and tribute to the film’s legacy.
Director Rob Reiner tragically was killed on December 14, along with his wife Michele Singer Reiner, in their Bretwood, California home.
Their son, Nick Reiner, was arrested and charged with their murders.
Billy Crystal
Then: Crystal starred as Harry Burns, a wise-cracking, deeply charming man whose friendship with Sally slowly deepens into love.
His performance anchored the film and showcased his timing honed from stand-up comedy and earlier film roles.
Now: Decades later, Crystal remains a beloved entertainer. He continued acting in film, television and theater, hosted the Academy Awards multiple times, and voiced memorable characters such as Mike Wazowski in the “Monsters, Inc.” franchise.
In 2025, he reunited with Meg Ryan for a nostalgic commercial recreating the movie’s famous Katz’s Deli scene for a Super Bowl ad.
Meg Ryan
Then: Ryan portrayed Sally Albright, the optimistic and curious counterpart to Harry’s cynical worldview.
Her performance became one of the defining romantic comedy roles of the late 20th century and helped cement her status as a leading lady in Hollywood.
Now: Ryan, now also a director, has worked behind the camera in recent years and in 2023 released the romantic comedy “What Happens Later.”
She has also revisited the “When Harry Met Sally…” legacy with Crystal, hinting at “something iconic” in reunion projects and reprising the famous deli scene decades after the film’s release.
Carrie Fisher
Then: Fisher played Marie, Sally’s sharp-witted best friend whose own romantic life offered comic relief and heartfelt moments.
Now: Fisher, beloved for her work in “Star Wars” and her sharp comedic voice, passed away in 2016. Her portrayal in “When Harry Met Sally…” remains part of her rich legacy in film and culture.
Bruno Kirby
Then: Kirby appeared as Jess, Harry’s loyal best friend with his own blunt take on love and relationships.
Now: Kirby died in 2006 from leukemia. His performances in “When Harry Met Sally…” and other films are remembered fondly by fans of his work.
Steven Ford
Then: Ford played Joe, a minor but memorable role connected to Sally’s social circle.
Now: Ford stepped back from acting after his last credited role in “Transformers” (2007) and has lived a more private life away from Hollywood.
