Nineties Nostalgia The 20 Most Hilariously Heartwarming Rom-Coms!

Top 20 Romantic Comedies from the '90s

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If there’s one thing we hopeless romantics can blame for our sky-high, completely unreasonable expectations of love, it’s the glorious world of ’90s romantic comedies. You know, where everything is just so perfect and dreamy that it’s almost infuriating, but in the best way possible. Sure, the plots may be cheesy, predictable, and utterly impossible, but darn it if they aren’t absolutely charming.

The ’90s were the golden age of rom-coms. Iconic films like Clueless, Pretty Woman, and Sleepless in Seattle graced the silver screen, making us fall head over heels for the likes of Julia Roberts and Meg Ryan. These rom-com royalty stars had us swooning left and right as they fell in love with their impossibly cute colleagues on-screen. Seriously, it’s a wonder they had time for anything else besides falling in love.

So, why not treat yourself and dive into the best ’90s romantic comedies right now? Trust me, your heart will thank you.

Sliding Doors (1998)

If you’ve ever wondered how the smallest choices can change the course of your life, this movie is a must-watch. Sliding Doors follows the parallel lives of a woman who catches a train and one who misses it. Prepare to question everything you thought you knew about fate and destiny. Sorry!

Clueless (1995)

Ugh! As if Clueless wouldn’t be at the top of this list. If you haven’t watched this gem at least ten times already, then you haven’t truly lived, my friend. Cher Horowitz, the ultimate inspiration, navigates high school life while attempting to give a total makeover to a new girl named Tai. Fun fact for you Jane Austen fans: Clueless is loosely based on Emma.

Four Weddings and a Funeral (1994)

This is the movie that launched our beloved ’90s rom-com hunk Hugh Grant into stardom. Join a group of friends as they navigate the joys and tribulations of marriage and death. It’s a rollercoaster of emotions, but hey, that’s what makes it so memorable.

The Wedding Singer (1998)

Forget your typical rom-com formula where the comedy takes a backseat to the romance. The Wedding Singer is a hilarious ride from start to finish. Watch as Adam Sandler’s character, a wedding singer who gets jilted at the altar, falls for his new friend Julia, played by the lovely Drew Barrymore. Get ready for some serious cry-laughing moments.

There’s Something About Mary (1998)

This movie was an absolute sensation when it first hit the screens, and it’s easy to see why. It’s a perfect blend of hilarious and heartwarming. Imagine a man hiring a private investigator to find his high school crush, only to discover that he’s not the only one chasing after her. Cue the hilarity and the heartwarming moments.

As Good as It Gets (1998)

Did you know that As Good as It Gets is the most recent movie to win Academy Awards for both Best Actor and Best Actress? It’s a brilliant film that tells the story of a gruff novelist with OCD who falls for a waitress, the one person who can handle his peculiar behavior. Get ready for a quirky, heartwarming tale.

Jerry Maguire (1996)

If you’re trying to convince someone who doesn’t love rom-coms to join you for a movie night, Jerry Maguire is the perfect choice. Tom Cruise plays a sports agent who starts his own agency and ends up falling for his coworker, Dorothy, a single mother played by Renée Zellweger. It’s not all smooth sailing, of course, but that’s what makes it so compelling.

The Best Man (1999)

This movie has it all—romance, comedy, and drama. It revolves around Harper Stewart, who has a book about his romantic history leaked right before he’s set to be the best man at his friend’s wedding. Talk about a juicy secret threatening to ruin everything. Brace yourself for a rollercoaster of emotions.

How Stella Got Her Groove Back (1998)

Who says love has an age limit? Stella, a forty-year-old single mom, embarks on a trip to Jamaica with her bestie, Delilah. Little does she know, she’ll meet the incredibly sexy Winston Shakespeare, who happens to be twenty years her junior. Age is just a number, and this movie proves it with a sizzling romance.

Runaway Bride (1999)

Julia Roberts and Richard Gere reunited nearly a decade after their iconic film Pretty Woman for this romantic comedy. The story revolves around a girl, a guy, and a whole lot of weddings. While it may not quite match the charm of Pretty Woman, it’s still a delightful watch, filled with chemistry and ill-fated weddings to drool over.

Notting Hill (1999)

Ah, 1999 was quite the year for Julia Roberts. In addition to Runaway Bride, she graced the screen in the unforgettable Notting Hill. The undeniable chemistry between her and co-star Hugh Grant makes this movie an iconic must-watch. And let’s not forget that famous line: “I’m just a girl, standing in front of a boy, asking him to love her.” That right there is pure rom-com gold.

You’ve Got Mail (1999)

Sure, AOL chat rooms and dial-up internet may feel like a distant memory, but Meg Ryan and Tom Hanks bring their A-game to this incredibly sweet film. New York City serves as the perfect backdrop for their accidental, secret love story. And that final scene in Riverside Park? Prepare to shed a tear or two.

She’s All That (1999)

If there’s one movie that encapsulates the ’90s rom-com era, it has to be She’s All That. From its talented cast to the epic makeover sequence, this film has it all. Plus, it features an unforgettable choreographed dance number and the late Paul Walker. Need we say more?

10 Things I Hate About You (1999)

In the battle for the ultimate ’90s rom-com, 10 Things I Hate About You gives She’s All That a run for its money. Inspired by The Taming of the Shrew, this movie combines a stellar cast, including Joseph Gordon-Levitt, Julia Stiles, and the late Heath Ledger, with a fresh and fun spin on classic material. Who could resist this gem, complete with a paintball scene?

My Best Friend’s Wedding (1997)

Is Julia Roberts the true queen of rom-coms? My Best Friend’s Wedding certainly makes a strong case. Though, yes, the plot may seem a little icky—hello, trying to break up your best friend’s wedding because you suddenly realize you’re in love with him?—Roberts brings such charm to the role that your heart can’t help but be won over.

Chasing Amy (1997)

Unrequited love is a classic rom-com theme, but Chasing Amy takes it to another level. Ben Affleck’s character chases after a woman who’s not interested in him—in fact, she’s not interested in men at all. This film pushes boundaries and explores the fluidity of sexuality and the complexities of friendship. It’s a modern and thought-provoking take on the genre.

Emma (1996)

Just one year after the powerhouse that is Clueless, Gwyneth Paltrow brings us another delightful adaptation of a Jane Austen novel. Emma Woodhouse, played by Paltrow, is a truly terrible matchmaker, but her dedication to love and happily ever afters keeps her going. Settle in for some divine costumes and brilliant wit.

While You Were Sleeping (1995)

Sandra Bullock delivers an endearing performance in this sweet and slightly complicated rom-com. Imagine falling in love with a guy in a coma, but then things get even more tangled when you find yourself involved in a lie pretending to be his fiancée, only to fall for his brother and his whole quirky family. It’s messy, but it’s also heartfelt, and Bullock shines.

Sleepless in Seattle (1993)

Ryan and Hanks team up for another classic rom-com, filled with all the nostalgia of a bygone era. Even though they spend the majority of the film apart, their accidental and almost magical love story is a joy to watch. And that final scene with the Empire State Building? Get ready for the waterworks.

Pretty Woman (1990)

Ah, the ultimate feel-good rom-com classic. Pretty Woman has all the dark undertones you could imagine, but it’s Julia Roberts’ infectious charm that keeps us coming back for more. Is there anyone more lovable than her when a jewelry box nearly crushes her hand and she laughs that iconic laugh? We think not! By the end of this movie, everyone is enamored with Roberts’ Vivian.

So, grab some popcorn, snuggle up on the couch, and let these ’90s rom-coms transport you to a world where love conquers all and happy endings are inevitable. You won’t regret it!

By Laura Hanrahan

Laura is a NYC-based freelance writer. When she’s not binging the latest true crime docu-series, she’s obsessing over all things Harry Styles, RHONY, and John Mulaney. You can follow her on Instagram [@lauraehanrahan](https://instagram.com/lauraehanrahan)

Now, it’s your turn! Which ’90s rom-com is your absolute favorite? Share it with us in the comments below and let’s reminisce together!

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