The Ultimate 90s Chick Flick Movie Playlist

Let’s take a trip down memory lane…

Anybody else up for a chick flick marathon? 

Let’s set the scene... 

It’s Friday night, you’re with your girl friends having a catch up and you’re feeling nostalgic. 

You switch on the DVD player and slot in a chick flick, and the marathon begins!

Yes, there are new movies released every week BUT there’s something about rewatching our favourite chick flicks that just hits differently. From a time filled with romance, sisterhood, comedy and female empowerment, the 90s were filled with feel good (and emotional) chick flicks that we still obsess over today. 

From the awesome 90s fashion to teaching us lessons in love and friendship, the 90s provided us with the best of the best. 

Here are just some of our favourite chick flicks of the 90s:

Clueless (1995)

Where have you been if you haven’t watched Clueless at least once in your life?! 

Nothing quite screams 90’s chick flick like Clueless. It is basically the defining movie of the 90s (and we’re not just talk about chick flicks either). 

Clueless revolves around Cher, a wealthy high school student in Beverly Hills who initially appears superficial until Cher and her best friend Dionne, decide to give new girl Tai Fraiser a makeover. In the process, Cher realises she needs a spiritual makeover and discovers that there is more to life than clothes and makeup.

Clueless is a whole lot of movie with substance and style. From the memorable quotes to the iconic fashion, we are very much still obsessed with this movie.  

Oh and Paul Rudd… helloooo!

Whether you’ve seen the flick or not, it’s not what you imagine it to be. From honest female relationships to iconic fashion, Clueless has everything you could ever want from a chick flick and more! 

We’re guilty of shopping for a yellow plaid skirt after watching it too.

Pretty Woman (1990)

Another movie that just never gets old.

First of all can we all just agree that Julia Roberts is the queen of ‘90s chick flicks?!

When it comes to 1990s chick flicks, Julia Roberts is pretty much a walking billboard for the majority of them and we’re so here for it! 

A recurring theme with 90s movies is the incredible fashion and the fashion in Pretty Woman trumps them all. 

Vivian’s style transformation will forever go down in history. From “lady of the night” to “high-class lady” - iconic. 

Let’s face it, back in the 90s Julia Roberts could’ve played a psychopath and we would have all been asking where she got her outfit. 

Yes, it’s not your typical love story but that’s what makes this movie so amazing. There are too many outstanding moments in the movie that we’ve lost count. 

And let's not forget the incredible soundtrack that goes with this movie. 

Pretty Woman stands the test of time and remains a classic with each new generation that watches this movie for the first time.

Never been Kissed (1999)

“All you need is for one person to think you’re cool, and you’re in. Everyone else will be scared to question it.”

There’s a small handful of people who would jump at the chance to return to high school in their adult years and Josie is one of the brave ones.

Starring Drew Barrymore, Never Been Kissed is about Josie, a copywriter for the Chicago Sun-Times, who goes undercover as a high school senior to find a gripping story. Instead, she discovers what it is like to be a student today versus when she was in school. 

Imagine a remake of this movie in 2022? Think we can all agree that the scenes in school today would be VERY different to what it was like back in the 90s. 

What would it take to get you to go back to High School? 

Drive Me Crazy (1999)

Who remembers Sabrina the Teenage Witch? Well, Sabrina is not so witch-like in this 1999 chick-flick. 

Drive Me Crazy stars Melissa Joan Hart and Adrian Grenier in an unlikely love story. Basically a go-to high school romance. In case you’re thinking, what is Drive Me Crazy and why have I never watched it?! Well here’s the lowdown…

Nicole and Chase used to be BFFs, then junior high happened. The high school dance is coming up but Nicole gets dumped. So does Chase. They stage a relationship to get at their exes. They visit each other’s worlds. Is love in the air? You’ll have to watch it to find out!

AND that’s not all! Britney Spears’ smash hit song Drive Me Crazy also featured in the movie and the music video for the song even features the movie’s two lead actors! Do we really need to say anything more?!

10 Things I Hate About You (1999)

From the outfits to the star studded cast, no 90s movie watchlist would be complete without 10 Things I Hate About You. This movie takes you on a roller coaster ride of emotions and captures teen drama, fear, and exploration perfectly alongside modernising Shakespeare in such a clever way.

The underlying message is about being true to yourself and that “you don’t always have to be who they want you to be”.

This movie teaches you that it doesn’t matter what’s on the outside. It’s what’s on the inside that counts.

10 Things I Hate About You is just as iconic now as it was back in the 90s and we absolutely love it!

She’s All That (1999)

She’s All That was your typical high school prom king and queen story. Freddie Prinze Jr. played the most popular kid in high school who accepts a dare to make the school’s outcast (played by Rachael Leigh Cook) into the prom queen. 

This movie demonstrates that love can be found in unlikely places, with people we least expect. 

She’s All That is an absolute classic. It’s light-hearted, an easy watch and recognises valuable life lessons about being honest and that there is always change for redemption if you are genuine about your feelings.

My Best Friend’s Wedding (1997)

This has got to be one of Julia Roberts’s best movies. With a relatable storyline that most of us can appreciate, My Best Friend’s Wedding is all about true love, friendship, and learning to let go for others’ growth. 

My Best Friend’s Wedding teaches us why it’s never a good idea to make one of those deals where you and your best friend promise to marry each other if no one better comes along.

You’d be lying if you said you didn’t go on an emotional rollercoaster when watching this movie.

Notting Hill (1999)

Julia Roberts and Hugh Grant falling in love. What more could you want from a chick flick?! 

If there was one thing that Notting Hill taught us, is that it’s to keep your language simple and straight to the point.

“I’m also just a girl, standing in front of a boy, asking him to love her.”

This movie follows the story of William Thacker, a simple bookshop owner whose life is forever changed when he meets the most famous film star in the world.

The chemistry between Julia Roberts and Hugh Grant is what makes this movie and will most definitely have you wanting to wander down to Notting Hill to find love on Portobello Road!

Think it's safe to say that we'll always have a special place in our hearts for the 90s and its chick flicks. We’re yet to find a 90s chick flick that we haven’t adored and we’re still watching them in 2022!

What are some of your favourite 90s chick flicks?

Let us know in the comments below!