The year is 1988 and a young actress named Meg Ryan has a choice to make: Stay committed to a vital supporting role in Steel Magnolias or drop out to star in When Harry Met Sally.
Of course, movie lovers all know what happened next: Ryan chose the latter, which proved to not only be a fateful decision for her career—When Harry Met Sally turned her into one of the world's biggest movie stars—but for another star's as well, with fellow romantic comedy queen Julia Roberts taking over her part in Steel Magnolias.
When Harry Met Sally was the first of many romantic comedies Ryan would front, with audiences unable to resist her comedic timing and charming personality. And, after a 14-year hiatus from the genre she helped elevate, Ryan returned to the rom-com world in this year's What Happens Later, which the 62-year-old also directed.
Not that Ryan considers the movie, which pairs her with David Duchovny as exes who unexpectedly reunite at the airport, a conventional romantic comedy. Rather, she described it as a "love story."
"These characters are in their 50s. It's a different story than when you're in your 20s," she told Glamour. "I wanted to make something beautiful and offer a new way of thinking about what love is."
It was a fitting endeavor for an actress who largely shaped how a generation of moviegoers view romance, thanks to her work in some of cinema's most iconic feel-good films. Some of them, of course, were written and/or directed by Nora Ephron, with Ryan dedicating What Happens Later to the legendary filmmaker who passed away in 2012.
"I believe in comfort movies," Ryan said. "In the movies I did with Nora, the characters lead separate lives, but whatever was happening, they were destined to find one another. There's a comfort in the kismet and the idea of an inevitable connection. It's a wonderland idea. It's an enchanted idea."
And What Happens Later proved Ryan is still as charming as ever. But how does her latest movie stack up against the eight other rom-coms she's starred in?
Get ready to have some thoughts because we ranked all of Ryan's rom-coms:
Addicted to Love
Despite its talented cast, led by Meg Ryan and Matthew Broderick as a revenge-seeking pair who pretend to date in order to get back at their former partners, this 1997 movie just puts the "meh" in Meg Ryan.
I.Q.
We're not sure why, but this charming 1994 rom-com is largely forgotten about, despite the fact that Albert Einstein (played by Walter Matthau) steps in as matchmaker for Ryan's intelligent doctoral student and Tim Robbins' everyman mechanic. Forget squared, you could say E = MC paired. (We're so sorry.)
What Happens Later
While the chemistry between Ryans, who directed this 2023 feature, and David Duchonvy was palpable, there was not enough romance or comedy. Still, it was refreshing to see such a mature take on a genre trope.
Kate & Leopold
Time travel meets rom-com in this 2001 film that pairs Ryan with Hugh Jackman as a 19th century duke who finds himself in New York.
Loopholes, nonsensical time travel and kind of insane ending aside, Kate & Leopold is cute and charming, so who really needs science?!
French Kiss
The plot was pretty complicated—a woman flying to France to confront hercheating fiancé finds herself in trouble when the crook seated next to her uses her to smuggle a stolen necklace in order to open a vineyard? Sure!—but Ryan and leading man Kevin Kline had a certainje ne sais quoi that made it all work.
Joe Versus the Volcano
Sure, audiences didn't initially erupt over this 1990 film—which marked her first pairing with Tom Hanks, more on that guy later—but it has developed a cult followng, thanks to its quirky premise and effortless chemistry between its leads. Alas, it's still an amuse-bouche for what was to shortly come...
Sleepless in Seattle
A rom-com where the leads only share one scene? It shouldn't have worked. And yet...we were all swept off our feet when Annie (Ryan) and widowed father Sam (Hanks) met at the top of the Empire State Building and realize they are MFEO in this 1993 classic. We don't want to be in love, we want to be in love in this movie.
Still, despite its fairy tale-esque nature, Sleepless in Seattle isn't dream team Ryan and Hanks' best movie.
You've Got Mail
While Sleepless in Seattle gave us a taste of Ryan and Hanks' onscreen sparks, consider Nora Ephron's 1988 take on The Shop Around the Corner a decadent six-course meal, filled with simmering tension, sophisticated banter, and the perfect blend of snark and sappiness.
Sure, the technology and references may be outdated (LOL, remember AOL?), Ephron's witty dialogue and its movie stars' pure, well, movie star-ness have made You've Got Mail timeless.
Alas, there is the dream, the dream of some other movie that is just slightly higher on our ranking...
When Harry Met Sally
Almost 35 years later, movie lovers will still have what she's having as this 1989 gem remains the gold standard of the rom-com genre.
A then largely unknown Ryan steals every scene she's in as the meticulous and high-maintenance Sally Albright, no easy task when partnered with comedy legend Billy Crystal. With one iconic fake orgasm, a star was born, with Ryan earning a Golden Globe nomination for her breakout role that simultaneously kicked off and cemented her run as America's Sweetheart.
Endlessly quotable—"Baby fish-mouth!"—and featuring knockout supporting performances by Carrie Fisher and Bruno Kirby, When Harry Met Sally has made it impossible to hate it.