Top 10 1990s Rom Coms That Still Got It

Say what you will about some of Adam Sandler’s misses - when he hits, he hits big. “The Wedding Singer” is a perfect example of this. It’s got loads of laughs, and he and Drew Barrymore have a chemistry that makes their love story believable and relatable. It's no wonder they worked on more films together after that. For one thing, their characters Robbie and Julia have an amazing rapport. Plus, the story — about a wedding singer and waitress who fall for each other despite her engagement to another man — is filled with heart and laughter alike. As a result, sentimentality brings a smile to our faces every time we press play.

There was tension on set during the filming of “Groundhog Day.” Indeed, there was conflict between director/co-writer Harold Ramis and star Bill Murray over the story’s tone. We don’t know who was in the right, but the true winner of the argument was the audience. You might think a movie about a guy having to relive the same day over and over again would get repetitive — but no. Sure, like Murray’s character Phil when he’s caught in the loop, we now know what’s going to happen. But rather than diminish the viewing experience, it actually makes us enjoy it even more. Not only that, you can’t deny the film’s legacy: nowadays, the term “groundhog day” is synonymous with repeated events or déjà vu experiences.

We’d say it’s ironic that “Reality Bites” made the list. But like Winona Ryder in the movie, we aren’t exactly sure how to define it. We’re joking, of course. What we do know though is that “Reality Bites” — about disillusioned youth — is often dubbed a seminal Generation X rom-com. That’s a generation that was largely seen as wanting to chill at the time. One reviewer described them as not seeing “any point in getting all bent out of shape and overambitious.” If you think about it, millennials and Gen Z get accused of being “lazy” in the same way. So while the music and clothes might have changed, “Reality Bites” still speaks to audiences today.

There’s something about this movie. Anyone who’s seen it will tell you that it’s inappropriate and gross, with boorish humor seen in things like the, well, non-traditional hair gel. Yet this 1998 Farrelly brothers film manages to elevate itself beyond a dumb, gross-out comedy. The tale of Cameron Diaz’s Mary and the guys who want to date her instead strikes a unique balance between the “rom” and “com.” This allows it to stand out as one of the genre’s most memorable offerings in the ‘90s, and it hasn’t lost its spunk. Years later, Ted and Mary’s relationship still works — so does the outrageousness in many ways. [“We got a bleeder”]. Some bits will simply never not be funny.

At first glance, one might not think a sweet, family-friendly rom-com about a rich man falling in love with a sex worker would work. We especially doubt many would’ve bet on it becoming one of the most successful romantic comedies of all time. But that’s exactly what “Pretty Woman” did, and here we are over 30 years later still talking about it. But it’s more than just discourse. We’re also still watching the movie, and loving the way it allows us to get lost in the “love conquers all” fairy tale dream of it. How many of us hope someone will romantically climb up our fire escape every time we see it play out on screen? There’s no shame in it!

It’s been over 25 years since “Jerry Maguire” came out. Yet when the time comes to pick something to watch today, we can often be heard yelling, “show me the movie!” It had us at hello in 1996, and nothing has changed. It’s a perfect rom-com, while also managing to be a sports and buddy flick. It also gives us a chance to see Tom Cruise doing something different than his now classic action movies. We get butterflies in our stomach as we see the titular sports agent pave his own career path while also finding (and fighting for) love. Not to get overly sentimental here, but “Jerry Maguire,” you complete us.

It has an 86% Rotten Tomatoes score and received an Oscar nomination for Best Picture. Basically, “As Good as It Gets” is almost as good as it gets when it comes to ‘90s rom-coms. Smartly written and character driven, it’s a mature and adult offering that still stays true to so many classic themes of the genre. That’s why it remains a pick that’s recognizable and comforting. We’d also be remiss not to mention Jack Nicholson as Melvin, a man with OCD who falls for Helen Hunt’s single mom Carol. They didn’t both win acting Oscars by accident. Their characters are complicated and their journey is by no means easy, but we root for them as much now as we did back then.

Shakespeare is timeless. So it only makes sense that a classic teen rom-com based on a play by the immortal bard would be one that’s still got it. 1999’s “10 Things I Hate About You” sets “The Taming of the Shrew” in high school, bringing us all the rom-com tropes we want. There’s everything from the grand gesture to the climactic declaration of love as the cynical Kat, portrayed brilliantly by Julia Stiles, finds romance. Let’s be honest, those things never get old. Also, for many, the movie was a first introduction to Heath Ledger. For that reason and many others, it will always hold a special place in our hearts.

In this day and age when meeting online is commonplace, there’s something almost prescient about “You’ve Got Mail.” Though dial-up is a thing of the past, the concept is one many of us can relate to today — maybe even more than we did back in 1998. Add to that the hidden identities and enemies-to-lovers plot between the owners of rival bookstores (one is a chain, one is a small local spot), and you get a winning formula. Tom Hanks and Meg Ryan together is just the cherry on top, with their charm bringing the whole thing home. We just have one more thing to say to “You’ve Got Mail”: you’ve got IT.

Before we unveil our top pick, here are a few honorable mentions.

“Notting Hill” (1999)
It’s Quaint, It’s Cozy, It’s Charming — What More Could You Want?

“My Best Friend's Wedding” (1997)
No Need to Say a Little Prayer, This Tale of Love, Friendship, & Growth Still Holds Up

“Sleepless in Seattle” (1993)
We’ll Always Stay Up to Watch Fate Win

“Clueless” (1995)
Everything from the Outfits to the Slang to the Plot Is Iconic

“While You Were Sleeping” (1995)
We Don’t Ever Want to Sleep Through the Heart & Hilarity on Display Here

No one saw “Four Weddings and a Funeral” coming. We’re sure the folks making it thought it was good and hoped it would do well. But we can’t imagine anyone dreamed that this movie — made for a little over $4 million — would see a box office haul of over $245 million. Did we mention it also got a Best Picture Oscar nomination? It’s easy to see why. We laugh and cry as we navigate these friends’ loves and lives with them, being served all the feels a romantic comedy should provide. Needless to say, we aren’t surprised that everything about this gem of a rom-com remains worth watching.

What is your favorite ‘90s rom-com that still holds up? Let us know in the comments