Rob Reiner Directed The Best Rom-Com Ever, And The Genre Was Never The Same

Have you ever enjoyed literally any romantic comedy made after 1989? Well, it exists because of "When Harry Met Sally..." and director Rob Reiner, who brought the film to life.

News broke late on December 14, 2025 ,that Reiner and his wife of 36 years, photographer Michele Singer, were found dead in their Brentwood, California home. There have been more developments about this horrific tragedy since that initial report, but that is, frankly, not what I'm here to discuss. The way that Reiner left this world feels particularly wrong because of the joy he brought into it. As an actor, Reiner was delightful in everything from "Sleepless in Seattle" to "The Wolf of Wall Street" to "New Girl." As a director? Reiner's range is unbelievable. It's astounding that the same guy made "Misery," "Stand by Me," "The Princess Bride," and "A Few Good Men." He also, as I mentioned, made "When Harry Met Sally..." with Nora Ephron, one of the greatest rom-com writers who ever lived.

"When Harry Met Sally..." stars Billy Crystal and Meg Ryan as the titular Harry Burns and Sally Albright, who end up carpooling as they both graduate from the University of Chicago and move to New York City to start their respective careers. To say they don't initially like each other is an understatement, but over time and decades, they become acquaintances, and then good friends, and then best friends. They end up spending the night together just once, and it ends in disaster before, in true rom-com fashion, they get their happily-ever-after. 

The movie is so much more than that, though; "When Harry Met Sally..." is a beautiful portrait of friendship, romance, and a journey through the lives of two richly drawn characters.

"When Harry Met Sally..." is many things. It's a love story. It's a tourism ad for New York City. It's a movie that features one of Carrie Fisher's best performances, and it's one of the most quotable films in cinematic history (how many times have you heard someone joke that they'll have "what she's having?"). It's also an in-depth character study of Harry Burns and Sally Albright that's got all the trappings of a romantic comedy — and influenced the genre for years to come — but has so much more depth than many other movies in said genre.

In 2019, while speaking to The Hollywood Reporter for the 30th anniversary of "When Harry Met Sally..." Rob Reiner said something incredibly profound about his own film: 

"What works about it is that the dance, it's really all about the dance, about what happens to two people, men and women, and what they go through, and I don't think it's changed much. I mean, the dating apps and all that stuff, but the basic dynamic between men and women hasn't changed, and I think that's what people hook onto." 

Unsurprisingly, Reiner was right. This story is timeless, and I think that's largely because the movie is so wonderfully funny and earnest at the same time. When Harry runs several city blocks of Manhattan to chase down Sally at a New Year's Eve party to confess his love for her, it's enough to make even the most cynical person believe that love is still out there for them.

You know how sometimes you'll be talking about movies with a friend or colleague and they note, "they just don't make 'em like this anymore?" It's very possible that they only said that because they just watched or rewatched "When Harry Met Sally..." Throughout the movie, Reiner smartly uses editing tricks and directorial flourishes to keep the story from feeling like a filmed stage play (it is a very dialogue-heavy movie, but Reiner was brilliant in his direction and never lets it feel bogged down by the banter).

Think of the split-screen phone call where Harry and Sally frantically call their best friends Marie (Carrie Fisher) and Jess (Bruno Kirby), who are now a couple, to freak out about the fact that they slept together the night before. Reiner utilizes a double split-screen as Harry and Sally provide different stories to Jess and Marie about what exactly happened during their unexpected night together, and it's not the only time he uses a split-screen effect. He also does that to show us Harry and Sally talking on the phone and watching "Casablanca" "together" on their respective televisions. With any other director, these split-screens might have looked stupid or cheap. Somehow, Reiner makes them work — and makes them sing.

I could talk about Reiner's masterful directing techniques and Nora Ephron's brilliant script and Meg Ryan and Billy Crystal's amazing performances forever, so I'll cut myself off at the pass. The entertainment industry lost a titan in Reiner, and most vitally, it lost a titan who approached storytelling with real heart and passion. Often imitated and rarely, if ever, duplicated, Reiner's legacy will last forever thanks to "When Harry Met Sally..."