Those of us who are obsessed with romantic comedies today likely discovered their magic during 1989 to 1999 in what's being dubbed the Golden Age of rom-coms. It's during this period that we not only had an abundance, but they set the benchmark for what we continue to look for in our romance movies and TV shows today.
The 2000s were also exceptionally solid, and we're even seeing a big boom today with a number of amazing new movies coming to our screens. But truly, few will ever top the magic of the Golden Age, and it's largely because so many of them have become classics today.
From the undeniable best one that is When Harry Met Sally (1989) to incredible adaptations like Clueless (1995), here are the best rom-coms of the Golden Age, as well as where you can stream them on platforms like Prime Video, Disney+, and more.
While You Were Sleeping (1995)
Every romance fan has one movie (if not more) that they can turn to when they're having a bad day, and as if by magic, it'll instantly make everything better. For me, that's always been While You Were Sleeping. Sandra Bullock is a rom-com legend for numerous reasons, but nothing will ever top the heart and wonder she evokes as Lucy, caught in the most unlikely love triangle, and paired with a scene partner with as much charisma as Bill Pullman.
The tropes within the film are generally almost impossible to play with, yet somehow, in While You Were Sleeping, every beat feels organic. Thirty years later, and every part of it still holds up as a story about finding love in the wildest circumstances while also discovering a family in the process. It's hilarious with a myriad of memorable lines, and so achingly romantic in the quiet moments where Jack and Lucy fall in love while Peter's in a coma. A perfect Christmas movie, a perfect rom-com, and an overall perfect movie all around.
When Harry Met Sally (1989)
When Harry Met Sally is the ultimate blueprint for opposites-attract romances. Nora Ephron's incomparable vision, coupled with Rob Reiner's screenplay, is a literal match made in heaven, brought to life by brilliantly sharp performances from both Meg Ryan and Billy Crystal. It's not only a perfect rom-com from the Golden Age (and maybe objectively the number one best), but it's also a stunning and cozy must-watch for the fall and winter seasons.
In large part, the appeal of When Harry Met Sally also comes from its rewatchability. It's not every movie you can revisit years and years after, but there's something about the comfort the characters evoke that makes their arcs so universal. At the same time, it's such a staple in the romance community that we now have a movie like People We Meet on Vacation (2025) that's so heavily inspired by the magic we find here. The concept of a classic doesn't just depend on the time that's passed, but on how the quality of the product continuously increases, and such is the case here.
10 Things I Hate About You (1999)
Most of the romantic comedies featured on this list are easier to relate to for those of us who are in our thirties now, but 10 Things I Hate About You was significant in our teen years, and the value of its narrative also comes from the detail that it still holds up. There were a number of romantic comedies that were released during these golden years, but the ones centered around teenagers typically don't hold up because of the dated archetypes.
And while 10 Things I Hate About You is far from perfect, it's still a solid example of excellence because of its cast, the screenplay, and the swoon-worthy joy it supplies as yet another opposites-attract romance. The themes also have tremendous value as a retelling of Shakespeare's Taming of the Shrew that explores societal expectations and adolescent angst in a manner that effectively sticks the landing. If you're concerned that movies from the decade won't be the same after a rewatch, you'll be surprised by revisiting this one.
You've Got Mail (1998)
Nora Ephron's trifecta ultimately belongs on every Golden Age rom-com list, whether you love them or not. While I typically appreciate the story in The Shop Around the Corner (1940) more, there's no denying the adaptation quality and insurmountable heart threaded into every frame of You've Got Mail. People often dream of seeing their favorite actors reunite for another movie, and it doesn't always turn out great, which is probably because Tom Hanks and Meg Ryan set an impossible standard.
It's largely because of their performances and because of how joyous the film is to revisit around the holidays that it continues to be such a triumphant win for the genre. When people reference the rivals-to-lovers and the pen pal trope, they often use them as an example, for it's through their portrayal that the appeal of the tropes grew even more romantic.
Cinderella (1997)
Both Ever After (1998) and Rogers and Hammerstein's Cinderella were released during the Golden Age of rom-coms, and while they're both sensational, it's impossible for me not to pick Cinderella. For those of us who grew up in the '90s, the movie was likely always on repeat anytime it aired on the Disney Channel. So if you want your rom-coms with a splash of magic and fairytale escapism, this will forever be the most enchanting version.
Like many of the movies on this list, a large part of their appeal lies in the casting. Do I really need to say more when we have iconic musicians like Whitney Houston and Brandy in one movie? No, I don't. Because if nothing else, the magic in this version has always been so beautifully transportive and stunning. Disney live actions continue to attempt to capture the appeal of the animated counterparts, but truly, so few will ever top Cinderella (especially for the Broadway aficionados.)
Father of the Bride (1991)
Father of the Bride is more of a comedy than a rom-com, but as an iconic feat in more ways than one, it absolutely deserves a spot on this list. Steve Martin and Martin Short are perfection—I dare you to watch without laughing out loud because it's impossible. And the entire premise is especially lovely as a film that honors platonic love as much as the act of getting married.
Plus, if the final scene is any indication, it is a rom-com. Annie and Brian have their moments to shine, and the way that George loves his wife, Nina (played to perfection by the late and legendary Diane Keaton), serves as an excellent showcase of romance, too. It's the way they stand as an example of how married couples can be and how there's warmth in the quiet moments when all the guests are gone. So if you're looking for a movie that's fun for the whole family, Father of the Bride is sure to be a hit.
Clueless (1995)
There's a significant amount of debate taking place right now about how "Wuthering Heights" (2026) diverts too drastically from the source material, and people are comparing it to Clueless as a retelling of Jane Austen's Emma. But unlike the present-day release that's dividing both audience members and critics, Clueless is a solid example of how to take the story you love and add your own modernized spin on it with original characters and a narrative that honors the heart of the novel.
Clueless isn't exactly a perfect rom-com, but it's a near-perfect adaptation that still holds up because of the friendships, romance, and, more importantly, the characterizations. As someone who studied Emma for years and believes Mr. Knightley is the ultimate book boyfriend, Paul Rudd's Josh comes pretty close to being exceptional. As another teen drama on this list, like 10 Things I Hate About You, Clueless is indeed worth watching over and over again.
Sleepless in Seattle (1993)
Whether you watch Sleepless in Seattle before or after You've Got Mail, it never matters because the masterful work that Hanks and Ryan deliver are top-tier to give us performances that effectively stick the landing and ensure that we see their different characters. Ephron's world is synonymous with romantic comedies for a reason, but the distinctly unique plot is what separates them despite familiar beats and comforting casting.
Obvious from the title, this one takes us out of New York and to Seattle, adding a distinct meet-cute and an even lovelier story about falling in love during unlikely circumstances. The magic of the movie also lies in the astute pacing and how the narrative delivers the type of earned conclusion that so many of us still think about to this day. Perfect for anyone who wants to believe in fate, there's nothing quite like it.
Notting Hill (1999)
If you've ever wanted the press conference in Roman Holiday (1953) to end differently, then Notting Hill might fix the hole left in your heart. The keyword here is might because the films are nothing alike outside of that small, distinct moment that's crucial to the narrative. But Notting Hill is one of the most well-known celebrity romances that brings two completely different people together in a way that works.
A large part of the film's appeal is the casting and, without question, the location. Surely, tourism in London grew shortly after the movie. The lived-in and deeply grounded spot of Notting Hill is a huge factor that makes the romance enticing because otherwise, the trope isn't an easy one to believe in. Julia Roberts delivers another sensational performance, but that's a given when you're as iconic as she is.
Four Weddings and a Funeral (1994)
In The Office's (2005) series finale, Michael Scott turns to the camera and says, "It's like all of my children grew up and married each other," and that bit has always weirdly reminded me of Four Weddings and a Funeral. The drama within the movie might be a bit much for people who prefer more mellow stories, but it's iconic for a reason, primarily for its cast.
As another movie on this list starring Hugh Grant, it can also be perfect for viewers who consider him their '90s romance king. More importantly, it's Andie MacDowell who's always stolen the show for me, and she's the reason it's as significant as it is. The extra dose of romantic relationships certainly helps, and there's also something wildly appealing about its title, which I'd say is one of the best ones on this list.
