10 of the best 90s rom-coms, ranked.

Romantic comedies really hit a sweet spot in the 1990s. 

There was Julia and Drew and Sandra and Hugh and Richard and Ben. 

There were ridiculous storylines that we just couldn't help but get swept up in. 

There were a lot of laughs. And there was always a happy ending. 

Here are 10 of the best 90s rom-coms, ranked: 

10. The Wedding Singer

Image: NewLine Cinema. 

Adam Sandler and Drew Barrymore give good rom com. 

The Wedding Singer follows the story of Robbie (Sandler) a wedding singer, who falls in love with a waitress named Julia (Barrymore) in the lead up to his own wedding. 

It's a funny tale about being with the wrong people and falling in love with the right person at the wrong time. 

Plus, what a soundtrack! 

9. There's Something About Mary

Image: 20th Century Fox. 


I think we all remember where we were when we first saw that infamous "hair gel" scene in There's Something About Mary.

Some of us were tweens and we've never really recovered from it. 

There's Something About Mary follows the story of Ted Stroehmann (Ben Stiller) who is about to go to the prom with his dream girl Mary Jensen (Cameron Diaz) when his scrotum gets stuck in his zipper. 

13 years later, Ted hires a private detective to track Mary down. But he soon realises he's not the only man who is obsessed with Mary. 

There's Something About Mary is heavy on com, and light on rom, and it showcases Diaz and Stiller at their comedic best. 

8. While You Were Sleeping

Image: Bueno Vista Pictures. 

While You Were Sleeping is an underrated gem. 

It follows the story of Lucy (Sandra Bullock), a Chicago Transit Authority token collector, who is obsessed with a man named Peter (Peter Gallagher) who buys a ticket from her every morning. 


When Peter is attacked and thrown onto the train line, Lucy saves his life and accidentally leads his family to believe that she's Peter's fiance. 

While Peter is in a coma, Lucy gets to know his loveable family, and starts to fall in love with his brother, Jack (Bill Pullman). 

7. My Best Friend's Wedding

Image: TriStar Productions. 

My Best Friend's Wedding is a movie about second chances and learning to let go. 

Jules and Michael have been best friends for years. But when Michael announces that he's marrying Kimmy Wallace, a college student eight years his junior, Jules realises that she may have missed her chance with him. 

My Best Friend's Wedding has all the elements of a bloody good rom-com - Julia Roberts' hair, a sing-a-long, a duplicitous bridesmaid and Rupert Everett as the ultimate gay best friend. 

6. You've Got Mail

Image: Warner Bros. 


You've Got Mail is screenwriter Nora Ephron at her best. 

The 1998 rom-com follows the story Kathleen Kelly (Meg Ryan) an independent bookstore owner who is in a relationship with a guy who she thinks is... fine. 

While in an internet chat room (remember those!) she meets a user named NY152. They hit it off immediately but Kathleen has no idea NY152 is Joe Fox, the heir to Fox Books, the mega bookstore that is opening up across the road from her shop. 

You've Got Mail is a movie about opposites attracting and how sometimes the worst thing possible can actually be a blessing in disguise. 

5. The Truth about Cats and Dogs

Image: 20th Century Fox. 

The Truth about Cats and Dogs is another underrated 90s gem. 

It follows the story of Abby Barnes (Janeane Garofalo), a vet and the host of a radio show called The Truth About Cats and Dogs. When photographer Brian (Ben Chaplin) calls into her show for advice, unexpectedly sends her a gift and calls her at work to ask her out; she agrees to meet. 

There's just one small problem. The woman Abby describes on the phone is actually her neighbour Noelle (Uma Thurman). 


Abby convinces Noelle to go on the date with her, and hilarious results ensue. 

4. Never Been Kissed

Image: 20th Century Fox. 

Look, is this movie slightly problematic through at 2021 lens? Yes. 

But is it bloody amazing? Yes. 

Never Been Kissed follows the story of 25-year-old copy editor Josie Geller (Drew Barrymore) who finally gets her big journalistic break. The only problem is she has to a return to high school, a place where she was ruthlessly bullied. 

When she returns to school, Josie discovers the kids still hate her, and she starts to develop feelings for her English teacher (Michael Vartan), who believes she's a 16-year-old girl. 

3. Sleepless in Seattle

Image: TriStar Pictures. 


All I can say is... MAGIC! 

Sleepless in Seattle is one of the best rom-coms of all time and I won't hear otherwise. 

Is it a ridiculous storyline? Yes. It is corny at times? Yes. But does it make you believe in taking chances? It sure does! 

The 1993 film follows the story of Sam Baldwin (Tom Hanks), who loses his wife to cancer and moves his young son Jonah to Seattle for a fresh start. 

One night, Jonah calls into a radio talkback show to talk about how lonely his dad is. The radio host convinces Jonah to put Sam on the line and millions of women across America fall in love with him. 

One of those women is Annie Reed (Meg Ryan), a Baltimore Sun reporter who convinces her editor to let her travel to Seattle to track Sam down. 

The rest as they say is... MAGIC. 

2. Pretty Woman

Image: Touchstone Pictures. 


Pretty Woman is one of the most iconic movies of the 90s, with several scenes firmly holding a place in pop culture history. 

It's also just a bloody good film. 


The movie follows the story of Edward Lewis (Richard Gere) a high powered corporate raider who buys struggling companies and sells them off in pieces for profit. 

While in his way to the Regent Beverly Wilshire Hotel late at night, Edward stops and asks a sex worker named Vivian Ward for directions. 

She accompanies him to the hotel, and they end up spending the week together. 

During that week, Vivian teaches Edward how to have fun again, and he teaches her that she's deserves more than what she's settled for. 

1. Notting Hill

Image: Universal Pictures. 

The movie featuring the most awkward, bumbling, fumbling, floppy-haired version of Hugh Grant was always going to make the top of my list. 

I bloody love this movie. 

Notting Hill follows the story of divorced bookstore owner William Thacker (Grant), who works in his bookstore all day and then comes home to his eccentric housemate Spike (Rhys Evans). 

Will thinks his life will always be this way until one day Hollywood star Anna Scott (Julia Roberts) walks into his store. 

This movie tells a fantastical, unbelievable story, against a backdrop of loveable genuine characters - a combination which makes you fall in love with it, time and time again. 

Keryn Donnelly is Mamamia's Pop Culture Editor. For more of her TV, film and book recommendations and to see photos of her dog, follow her on Instagram and TikTok.