Few romantic comedies have the enduring legacy of “When Harry Met Sally…” Written by the incomparable Nora Ephron and directed by Rob Reiner, the film explores an eternal question: Can men and women ever just be friends?

R”When Harry Met Sally…” bewitched audiences with its excellent down-to-earth realism, thanks to a script that ranks among the best of Nora Ephron’s career, and the film would go on to be one of the biggest hits of 1989. For some of the cast, “When Harry Met Sally…” was jusr the latest role in a long filmography, while for others it was their breakout hit. But for all of them, “When Harry Met Sally…” has endured as one of the jewels of their careers: a perfect alchemy of comedy and heart that stands the test of time.

Here is what happened to the main cast of “When Harry Met Sally…” in the years since the film’s release.

Billy Crystal first made a name for himself as a stand up comedian. He had his first breakthrough in television when he appeared on the soap opera parody sitcom “Soap” as Jodie Dallas, who is recognized as the first unambiguously gay character in a TV show. Crystal and director Rob Reiner had a long standing friendship, and the two worked together first on “This Is Spinal Tap,” in which Crystal appears as Morty the Mime, and later in “The Princess Bride” as Miracle Max, which Crystal improvised almost every single moment of.

Reiner clearly knew and respected Crystal’s comedic chops, but as he was looking to cast the role of Harry, he hesitated to cast Crystal, knowing the role would require serious dramatic moments. If Crystal couldn’t live up to those moments, it could jeopardize their long friendship. Eventually Reiner relented and Crystal proved himself more than capable, earning a Golden Globes nomination for his performance.

With this hit under his belt, Crystal would prove himself to be a true showman, hosting the Academy Awards a record nine times from 1990 to 2012. He continued to write, direct and perform in everything from major comedies like “Analyse That” to voice performances in Pixar’s “Monsters Inc.” and the English dub of Studio Ghibli’s “Howl’s Moving Castle.”

Crystal would also return to Broadway with an adaptation of his film “Mr. Saturday Night,” which won him a Tony. Over the years, Crystal has established himself as an elder statesman of entertainment, hosting various awards and eulogizing friends like Robin Williams and Muhammad Ali. In 2023, it was his turn to be honored at the Kennedy Center, where his “When Harry Met Sally…” collaborators Rob Reiner and Meg Ryan were on hand to celebrate his accomplishments.

Before she was “America’s Sweetheart,” Meg Ryan was an up-and-coming actress building a resume across small parts like the film “Rich and Famous” and the soap opera “As the World Turns,” as well as various commercials. Then she started to work her way up the call sheet with supporting parts in the blockbuster “Top Gun” where she played the wife of Tom Cruise’s wingman Goose, and in 1987’s underrated Joe Dante adventure film “Innerspace,” where she met her future husband Dennis Quaid.

Her career truly blew up with “When Harry Met Sally…”, her first lead role in a film, which earned her a Golden Globe nod and made her a star. Afterwords, she starred in a string of hits, including “Sleepless in Seattle” and “You’ve Got Mail,” which were also written by Nora Ephron. These roles made Meg Ryan the queen of romantic comedies, but in 2003 she made the dramatic choice to break away from that sweetheart image by starring in Jane Campion’s dark erotic thriller “In The Cut.” The controversial film was the beginning of a new stage of her career where Ryan would only work sporadically in independent projects, largely leaving Hollywood behind.

“When Harry Met Sally…” remains the capstone of her career, although her son Jack Quaid has picked up the slack, quickly becoming a reliable leading man for studio and independent projects alike thanks to the charisma he inherited from his mother Meg.

Born to singer and TV entertainer Eddie Fisher and “Singing in the Rain” star Debbie Reynolds, Carrie Fisher was destined to be on the silver screen. After a small but impactful role in Hal Ashby’s “Shampoo,” Fisher became the immortal Princess Leia in 1977’s “Star Wars,” and from that point on, Fisher was a star in her own right.

With her devilish wit, Fisher also made a name for herself as a writer with 1987’s “Postcards from the Edge,” a semi-biographical novel about her relationship with her mother. The book would go on to be adapted in 1990 into a film starring Meryl Streep as her analog and also featured Meg Ryan’s husband Dennis Quaid as her thinly veiled stand-in for Harrison Ford.

Fisher played Tom Hanks’ wife in Joe Dantes’ “The ‘Burbs,” which released the same year as “When Harry Met Sally…” After that, Fisher would pop up in a variety of comedies to lend her wit and gravitas wherever it was needed, like in “Austin Powers: International Man of Mystery,” “The Wedding Singer,” and “Jay & Silent Bob Strike Back.”

Behind the scenes, Fisher also made a name for herself as an accomplished script doctor, coming in to punch up scripts for film and TV. Then, in 2013, Disney purchased Lucasfilm and announced a new sequel trilogy with Fisher and co. all returning to reprise their roles. Fisher was a lively part of the press tour for “The Force Awakens,” and did some of her best work in “The Last Jedi.” But prior to the film’s release, she suffered a medical emergency on a flight to Los Angeles and tragically passed away on December 27, 2016. When “The Last Jedi” premiered a year later, it was dedicated “in loving memory of our princess.”

Film critic Leonard Maltin called Bruno Kirby “the quintessential New Yorker or cranky straight man,” and he made a name for himself in parts throughout hit comedies like “Modern Romance,” “This is Spinal Tap,” and “Good Morning, Vietnam.”

“When Harry Met Sally…” was the first movie Kirby starred in alongside Billy Crystal, followed by “City Slickers” in 1991. In both films, Kirby played Crystal’s best friend, but in real life they had a falling out during pre-production on “City Slickers II: The Legend of Curly’s Gold.” The story goes that Kirby demanded script changes that Crystal refused, and in the end, his part was taken over by Jon Lovitz.

After that, Kirby would appear in the movie “Stuart Little” and be a regular performer across TV shows like “Mad About You,” “Homicide: Life on the Streets” and “Entourage.” Kirby passed away on August 14, 2006 after complications related to leukemia at the age of 57.