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.
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?!
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Sure, the technology and references may be outdated (LOL, remember AOL?), Ephron's witty dialogue and its movie stars' pure, well, movie star-ness have made You've Got Mail timeless.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.