If you love 2000s chick flicks like I do, this was a tough list to put together, but someone had to do it. Originally this list was going to be 10, but I thought I’d make my life harder and write my top 5 to make sure they were really the top tier. Also, this is not a ranking because that would be even tougher, so instead these are in order of release dates.
For context, what I like in a chick flick:
- a makeover/glow up
- excellent style
- new girl
- friendship drama
- a cute boy
- an A list chick flick actor (eg. Hilary Duff, Amanda Bynes, Lindsay Lohan)
- genuine laugh-out-loud humour
1. Legally Blonde (2001)
This movie is one of the reasons why I love chick flicks: it shows you that it’s not mutually exclusive to be girly and be smart, which is what some 2000s movies imply. Elle Woods starts the movie sweet and girly and pink and she ends the movie sweet and girly and pink… as well as being a strong lawyer with a new boyfriend and an enemy turned friend. When she uses her knowledge of haircare to win her case, it is *chef’s kiss* fantastic.
I’ve never seen another movie quite like Legally Blonde, which is unique in its focus on school and career. I believe that has to do with the cast not being in high school, which makes it a movie that appeals more the older I grow up. You don’t have to leave your girliness behind in adolescence. You can have it all–the girly, the partner, the friends, the style, and the career.
I’m waiting for the medical version of this movie, Hollywood.
2. What a Girl Wants (2003)
Who wouldn’t love finding out that their long lost father is actually a very big deal across the pond and has a beautiful house with opportunities to meet a bunch of beautiful people wearing beautiful clothes? It’s a fun story that would never happen in real life, but that fantasy angle of the movie is what makes the movie such good escapism–and that’s what I’m ultimately looking for in a chick flick.
To be a good chick flick–an actually genuinely good chick flick–your movie needs to be grounded by a solid story with solid actors, and Amanda Bynes and Colin Firth do just that in this film. Amanda Bynes was the queen of comedy back in the day–I almost included She’s the Man–and she does a perfect mix of bubbly humour that she wholeheartedly commits herself to. Additionally, I saw this movie before I even knew who Colin Firth was, but even my little kid self could tell he was more special than your average estranged father. The scene where he rocks out in leather pants? So cringey. But he sells it like no other.
3. Mean Girls (2004)
I debated about leaving this out because wow, recommending Mean Girls, how original, but it really is worthy of its spot here. Mean Girls is a true classic in the way you read Shakespeare in class and you realise that humans have been the same for eons, it’s just the setting of the characters that’s different. Sure, maybe it’s a modern day classic–I doubt it was possible to spread rumours so fast back in the day–but even though society has changed and the technology has evolved, the overall lessons of the movie are still very relevant almost 20 years later.
Not only is the movie genuinely funny with a lot of legendary one-liners that I don’t even have to mention, it showcased great actors perfectly cast for their part, as well as important lessons about what being a modern teenager means. Dumbing yourself down or changing yourself for the attention of a boy, the subtle expectations society has for every aspect of body (it’s not just weight!) as well as the complex and everchanging dynamics of female friendships. The humour alone could have carried the film, but the messages are what make it an absolutely worthy classic.
4. A Cinderella Story (2004)
I know everyone loves Lizzie McGuire, but for me this is Hilary Duff at her finest (we’ll add Chad Michael Murray too because honestly, I haven’t seen One Tree Hill). What can be said other than the iconic lines in this film (off the top of my head, I can name “no dad, I’m throwing away yours” and “waiting for you is like waiting for rain in this drought”), Princeton being the school of choice for the princes and princesses (so smart!), and the amazing diner aesthetic?
This movie sparked at least half a dozen remakes of modern Cinderella versions that were honestly terrible compared to this one. I don’t mind twists to Cinderella as long as it works, but a lot of them simply didn’t work. This movie did a classic version of modern Cinderella and it did it very well: the beautiful ball gown, innocent and doe-eyed Hilary Duff, and a sweet relationship between our two leads based on feeling misunderstood that is a necessary addition to any modern Cinderella. It is infinitely satisfying when a movie does a classic right.
5. Angus, Thongs and Perfect Snogging (2008)
This movie has been described by my friends as juvenile, which just means it’s not acceptable because they’re on the younger side and they act like it. Kind of. Still, though Georgia and her friends are pretty immature, it’s an immature that feels honest and real at the age of 14. I distinctly remember worrying about my looks and feeling like uncool was a disease and being embarrassed because you didn’t know the right thing to wear at a party. Though I never wore an olive costume.
It’s the willingness of this movie to commit to the cringiness of being a young teenager that makes it, because it feels true to the experience of being a teenager. The truth is, it’s very difficult for most of us to know how to be cool, let alone at 14. When you’re older, you’ve learned a few tips on how to fake fitting in, but really being cool just matters less as your world expands. We’re not really much better at it just because we’re older, we just don’t need to be and we hide it better. I don’t know many movies that really show all of the good, the bad, and the ugly of being a teenager quite like Georgia’s movie does.
Honourary Mention: To All the Boys I’ve Loved Before (2018)
I’m cheating, but I wanted to give a shoutout to this movie because it gives Asian representation… which points to one of the problems with 2000s movies and culture overall. These movies do not hold to a 2021 standard. Though I lament at the fact that there will not be more 2000s movies, chick flicks need to reflect the society that young girls and women live in, and it is hard to argue that our culture has progressed in some very valuable and necessary ways.
Barring the Asian representation and a more modern shift, this is also just a genuinely good film. Lara Jean has the excellent style required of a great lead character, and the story’s focus on old-fashioned letters brings a call back to a time before our current digital age. Fake relationships are a classic chick flick trope, and Peter Kavinsky plays a great modern hero: open-minded in trying new things, and unafraid to wear his girlfriend’s scrunchie on his wrist without appearing masculine. It’s a movie that balances out modern and old-fashioned in just the right ways, while staying sweet and true to the spirit of 2000s films.
Well, there it goes. My 5 favourite 2000s chick flicks. I’d be interested in learning yours down below!