12 ’90s Rom-Coms That Deserve a Rewatch

We’ve never needed romantic comedies more than we do right now.

I am personally so grateful for the existence of this particular film category and am not even a little bit embarrassed to admit that I’ve been watching at least two a week during this current lockdown.

Not only do rom-coms give us a satisfying dose of laughs, but they also give us happily ever afters that make us blissfully hopeful. And that is the exact energy we need right now.

When it comes to rom-coms over the decades, the ’90s did it best, with actors like Hugh Grant, Drew Barrymore, Julia Roberts, Adam Sandler and Heath Ledger coming onto the scene with electric love scene chemistry and iconic characters that catapulted them into the spotlight.

So, tonight, why not cuddle up with yourself, a block of chocolate and a bottle of wine, and indulge in one of these iconic rom-coms from the 90’s? Here are 12 of our favourites.

She’s All That (1999)

Here, we have a classic ‘boy falls in love with nerdy girl by accident’ storyline, and we love every minute of it. Starring mid-90’s hunk Freddie Prince Jnr as prom king Zach, who’s not only tall, handsome and cool, but also a really sweet guy at heart, this rom-com is feel-good with some pretty great fashion and celebrity cameos to boot.

10 Things I Hate About You (1999)

This flick is an absolute classic, with a stellar cast including Julia Stiles, Heath Ledger, Joseph Gordon Levitt and Allison Janney. It’s all about high school politics, first loves and heartbreaks. Oh, and Heath Ledger has an iconic singing scene, which might be his sexiest moment on screen – ever. A 10/10 must-watch.

Clueless (1995)

Ugh, as IF! Clueless is ICONIC. Its iconic outfits, one-liners and character arcs have made this film a pop culture masterpiece that’s still relevant today. The film is about rich, entitled and stuck-up Cher (Alicia Silverstone), who’s learning to cope with being a teenager and all the drama that comes with it. She helps new student Tai (Brittany Murphy) gain popularity and, in the process, discovers her own feelings for someone unexpected.

Notting Hill (1999)

A personal favourite of mine, Notting Hill is all the things a good romantic comedy should be: funny, sad and too good to be true. It’ll have you laughing, crying and wishing that you owned a cute little bookstore in Notting Hill. Julia Roberts plays the world’s most famous actress while Hugh Grant is the book store owner she falls in love with.

Cry Baby (1990)

Cry Baby is a film that doesn’t really fit into one category or genre. It’s a musical romantic comedy, with traces of drama and theatre. Johnny Depp plays a motorbike-riding juvenile delinquent (shocker), who seduces beige good-girl Allison. Together, they cause ruckus in Baltimore. It’s seemingly set in the 1950’s, with a very Grease-like energy to it.

Never Been Kissed (1999)

A Drew Barrymore classic, Never Been Kissed is about a girl who gets to rewrite her high school history and find the man of her dreams along the way. It’s cheesy, but entirely relatable.

Strictly Ballroom (1992)

Baz Lurhmann’s first-ever film and, in my opinion, one of his best. Strictly Ballroom takes us into the over-the-top drama that is the world of ballroom dancing, with ridiculous rules, upper-middle bogans and terrible fake tan. This is a film about dancing, creative expression, taking risks and not judging a book by its cover – all with a bit of Baz Luhrmann charm.

Pretty Woman (1990)

Richard Gere and Julia Roberts are perhaps the most attractive rom-com couple in living history and in this juicy flick, it’s a boy-meets-hooker love story. We’re going to overlook the general misogynistic story-arc of this film because its fairytale quality is what makes this film so charming. Also, Richard Gere is a 10/10 babe.

The Wedding Singer (1998)

Robbie (Adam Sandler), a wedding singer, meets Julia (Drew Barrymore), a waitress, at a reception and the two hit it off. But alas, she is engaged to another man who treats her badly. Robbie decides he must stop herwedding and his plan is ICONIC. Adam Sandler and Drew Barrymore are the perfect rom-com duo. It’s funny and endearing and will have you feeling optimistic about romance, which is what we’re all here for, right?

Mrs. Doubtfire (1993)

Mrs Doubtfire isn’t your typical rom-com, but we couldn’t not include it. Robin Williams is at the centre of this film, playing a dad who is on the cusp of losing custody of his kids. He takes matters into his own hands and transforms into Mrs Doubtfire, a quirky, yet qualified nanny. This film is hilarious and packed full of love. Get your tissues ready.

The First Wives Club (1996)

The First Wives Club stars Hollywood queens Goldie Hawn, Diane Keaton and Better Midler – need we say more? They play best friends who re-connect when their husbands all leave them for younger models, and the ‘first wives’ set out to seek revenge. It’s feminism before feminism was truly known.

Runaway Bride (1999)

Another Julia Roberts and Richard Gere special right here. Julia Roberts plays Maggie Carpenter, who has run away from her own wedding three times. Richard Gere plays a reporter who covers a story on her, which gets him fired, so he goes to check out the situation for himself… and you guessed it, they fall in love.