If us hopeless romantics can thank *one thing* for our entirely unrealistic expectations of love and partnership, it's romantic comedies from the 1990s. You know, where every girl has a meet-cute with her dream man (even if she doesn't know it yet!), their relationship develops at lightning speed, and then, after one over-the-top grand gesture, they realize they're perfect for each other and live happily ever after in Movieland™. Sure, the plot is cheesy, predictable, and unfeasible, but it's also completely charming.
The '90s were a decade of rom-com gold. It’s when a LOT of the genre's most iconic films hit movie theaters—seriously, to name just a *few* highlights, Clueless, Pretty Woman, and Sleepless in Seattle. Julia Roberts, Meg Ryan, and other members of rom-com royalty starred in hit after hit after hit—seems like they had time for nothing else besides falling in love with their cute colleague on-screen.
Because I know you have the time, why don't you work your way through this list of the best '90s romantic comedies starting...right now?
Sliding Doors (1998)
If you've ever wondered how different your life would be if you had just done even the smallest thing differently, then this movie's a must-watch. It follows two possible (and very different) storylines of one woman's life: one where she made a train, and one where she missed it. It's an excellent movie that may or may not have you questioning everything. Sorry!
Clueless (1995)
Ugh! As if this wasn't going to be top of the list. If you haven't seen Clueless at least 10 times by now, then you haven't lived, my friend. Cher Horowitz is an inspiration as she tries to navigate high school life and give a full-on makeover to the new girl in school, Tai. Fun fact for all you Jane Austen fans: the movie was actually loosely based on Emma.
Four Weddings and a Funeral (1994)
This is where classic '90s rom-com hunk Hugh Grant got his big break. He takes the lead in this movie, which follows a group of friends as they deal with two of life's most inevitable events: marriage and death.
The Wedding Singer (1998)
You know how a lot of rom-coms are heavier on the rom than the com? Not this one. Adam Sandler is guaranteed to have you cry-laughing while watching this movie. He plays a wedding singer who gets left at the altar at his own wedding; eventually, he begins to fall for his new friend Julia (aka Drew Barrymore).
There’s Something About Mary (1998)
This movie was huuuuge when it first came out, and for good reason: it's equal parts hilarious and cute. Twenty-nine-year-old Ted hires a private investigator to find his high-school crush, Mary—but the PI ends up falling for her himself, and soon discovers that he's not the only one going after her.
As Good as It Gets (1998)
Here's a lil industry trivia: As Good as It Gets is the most recent movie to take home Academy Awards for both Best Actor and Best Actress. It's about a gruff novelist with OCD living in New York City who falls for a waitress—the only server at his regular diner who puts up with his behavior.
Jerry Maguire (1996)
This is a good option if you're trying to convince a non rom-com lover to watch along with you. Tom Cruise plays a sports agent who leaves his job to start his own agency, and the only coworker who decides to come with him is 26-year-old single mother Dorothy, played by Renée Zellweger. They start to fall for each other, but obviously, it's not all smooth sailing.
The Best Man (1999)
This movie's got it all: romance, comedy, and drama. When a copy of Harper Stewart's yet-to-be-released book based on his past romantic dalliances leaks right before he's set to be the best man at his friend's wedding, he tries to keep it under wraps, scared that a secret about him and the bride-to-be will get out. Yowza.
How Stella Got Her Groove Back (1998)
Forty-year-old single mom Stella agrees to go on a trip to Jamaica with her bestie Delilah. While there, she meets the super sexy Winston Shakespeare, who just so happens to be 20 years younger than her. But since age is just a number, the two have a full-blown romance. Hot.
Runaway Bride (1999)
Nearly a decade after they made the gold standard Pretty Woman, Julia Roberts and Richard Gere reunited with director Garry Marshall for the story of a girl, a guy, and a whole lot of weddings. The movie isn't as charming as Pretty Woman—a tall order for any film—but there's still something special about seeing these two on screen as a mismatched pair desperate to prove they're not totally nuts about each other. Special bonus: a bunch of (ill-fated) weddings to drool over.
Notting Hill (1999)
Roberts had quite the year in 1999, churning out Runaway Bride and Notting Hill, which both hit the big screen that summer. Notting Hill is the more iconic of the two, thanks to the mega-chemistry between her and co-star Hugh Grant, but we all know the real reason why this one is so essential. Roberts' instantly classic plea to Grant: "I'm just a girl, standing in front of a boy, asking him to love her." That's rom-com glory right there.
You've Got Mail (1999)
Sure, the "we met in an AOL chat room" premise may be hopelessly dated—and the sound of literal dial-up internet is now akin to the Stone Age—but Meg Ryan and Tom Hanks romance the hell out of each other in this incredibly sweet film. It's one of those "oh, New York City is basically its own character" movies, and that's fine by me, because few things are as genuinely enjoyable as watching Hanks and Ryan fall in love with each other (secretly, accidentally) around various NYC landmarks. And that last scene in Riverside Park? Waterworks, every time.
She's All That (1999)
There are plenty of arguments to I.D. She's All That as the definitive '90s-era rom-com—the least of which that it co-stars Matthew Lillard as a dude famous for appearing on The Real World, perhaps the most '90s sentence imaginable—and most of them are hard to rebuff. The movie has it all: a solid makeover (remove ponytail and glasses, now you're done), Usher, a really great sequence that simply involves Rachael Leigh Cook walking down a stairway, Paul Walker (RIP), and the best (and most random) choreographed dance sequence in all of cinematic history.
10 Things I Hate About You (1999)
If She's All That is not the definitive '90s-era rom-com, than the real winner has to be 10 Things I Hate About You. A riff on The Taming of the Shrew, the movie combines an extremely talented cast (Joseph Gordon-Levitt, Julia Stiles, and the late Heath Ledger) and a super-fun light spin on timeless material. It also comes complete with a paintball season, because it was the '90s.
My Best Friend's Wedding (1997)
Is Julia Roberts our finest rom-com queen? She's definitely up there, and her ability to do the romance and the comedy in new and different ways certainly doesn't hurt. In the hands of another actress, My Best Friend's Wedding could be a little icky—this girl is going to break up her BFF's wedding because she suddenly realizes she's into him?!—but Roberts brings the charm so hard that you almost forgive her.
Chasing Amy (1997)
Unrequited love always makes for fine rom-com fodder, but this Ben Affleck-starring film pushes that idea to the brink. Instead of chasing a woman (Joey Lauren Adams) who's just not interested in him, he chases a woman who is not interested in any man. The movie unfolds in surprising fashion, toying with the fluidity of sexuality and the boundaries of friendship in equal measure, a thoroughly modern take on the genre.
Emma (1996)
Just one year after Clueless modernized Jane Austen's novel of the same name—to, like, totally awesome effect—Gwyneth Paltrow played dippy heroine Emma Woodhouse in a mostly faithful period adaptation. Just like Cher Horowitz, Emma is a horrible matchmaker, but her dedication to love, her friends, and happily ever afters keeps her trucking right along, blinding her to the actual affection she feels for the handsome Mr. Knightley (Jeremy Northam). The costumes are divine, the wit is even better.
While You Were Sleeping (1995)
Sandra Bullock falls in love with a guy in a coma—or, more precisely, she develops a crush on a dude who then falls (literally) into a coma, finds herself mixed up in a lie that she's his fiancée, then falls in love with his brother (and the rest of his family). It's a mess, but it's a sweet, sincere mess, and Bullock is top-notch.
Sleepless in Seattle (1993)
Ryan and Hanks appear in another dated masterpiece—who listens to radio call-in shows? who calls them?—but like You've Got Mail, the sweetness of the film transcends old-school technology. Ryan's Annie and Hanks's Sam are apart for the vast majority of the film, falling in love with each other sort of by proxy and definitely by accident. Also, any film that ends with the Empire State Building lit up like a big heart is undoubtedly essential.
Pretty Woman (1990)
Although it's got plenty of dark undertones, Pretty Woman has a lightness and joy to it that's totally due to Julia Roberts' mega-watt charm. Has anyone ever looked as appealing as Roberts does when a jewelry box nearly crushes her hand and she breaks out with that trademark full-mouthed laugh? No, they have not! Roberts' Vivian wins over Richard Gere's Edward with ease, but how could she not? By the time Pretty Woman is over, everyone is in love with her.
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