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“It’s October 3rd” – Movies From the 2000s That Shaped our Generation

This article is written by a student writer from the Her Campus at UVM chapter.

By: Isabel Petrou

We can all remember the first time we heard, “On October 3rd he asked me what day it was. It’s October 3rd.” From that moment, our lives changed. One can say this for any of the monumental chick flicks from the 2000s. I’d like to believe that we all have a little Regina George, Cher Horowitz, Mia Thermopolis, and more icons within ourselves. They truly shaped who I am today, and so did every other hit movie during the Y2K era.

As the crisp autumn air approaches, it is time to get cozy and open up any streaming platform while I name off the best memorable chick flicks of our generation:

Here is my top 14:

Mean Girls

Of course, we have to start with the first movie you think of when you think of Y2K. The only movie that has the most iconic quote about fall. Mean Girls truly is the movie for the girls. Also who else screams 2000s more than Lindsey Lohan herself? Of course, we cannot forget Rachel McAdams and Amanda Seyfried’s iconic performances. This movie follows Cady (Lohan) entering a new school where she encounters “The Plastics” aka the rulers of the school. This movie portrays every high school cliche to ever live. Oh and did I mention there’s LOTS of pink?

10 Things I Hate About You

It’s no lie that after watching this movie we all either became a Heath Ledger girly or a Joseph Gordon Levitt girly. No in-between. Kat Stratford is THAT girl when it comes to moody rebellious teenage girls. This movie stars Julia Stiles and Larisa Oleynik as sisters. Bianca (Oleynik) is not allowed to date until her older sister Kat (Stiles) does. This seems impossible until Patrick (Ledger) comes into the picture and can connect with Kat like no other (thanks to Cameron’s (Levitt) scheming all to get Bianca’s heart). The “Can’t Take My Eyes Off of You” scene still lives rent-free in my mind.

Confessions of a Teenage Drama Queen

You didn’t think I could go through this entire article without mentioning another Lindsey Lohan Movie, did you? Again, she is the face of the 2000s! Mary Elizabeth Cep (Lohan) is the classic teenage girl. However, she has a second persona named Lola who’s destined to become a movie star. Mary goes from living in the Big Apple to living in a normal town in New Jersey. Megan Fox plays the mean girl and as always, she delivers. Not to mention Lohan’s character is ultra obsessed with a boy band’s lead singer (hello Harry Styles prediction!).

How To Lose a Guy in 10 Days

Three words: the yellow dress. Common, I know we all wish we could be Kate Hudson in that yellow dress with Matthew McConaughey looking at head over heels. It’s a core memory. Andie Anderson (Hudson) is on a mission to write a piece on how to get a man to leave in 10 days and she wants to go full method acting on this assignment. Enter Ben Berry, the perfect victim. Except- he’s trying to make a woman fall in love with him in 10 days. This includes the ultimate enemies-to-lovers trope.


As if, I couldn’t forget to mention Clueless! Cher (played by Alicia Silverstone) is an authentic Beverly Hills it girl. She has it all: the mansion, the clothes, the car, and the status. As any other classic popular girl, Cher is on a mission to give the new girl a makeover. In the end, Cher learns a little more about herself and that she may be more than a pretty face. 

27 Dresses

If you didn’t dream of standing in a bar singing “Benny and the Jets” with the man of your dreams after watching this movie then did you even pay attention? In all honesty, I have never listened to the Elton John classic the same ever since. Katherine Heigl and James Marsden’s chemistry is off the charts in this movie. It follows professional bridesmaid Jane (Heigl) whose job is to do all things wedding (and be in them). One day she finds out her sister is marrying the love of her life and she immediately questions what she’s doing with her life. Then enters reporter Kevin who is invested in Jane’s sort of “sad” story. I still don’t know how she fits all those dresses in that small closet.

13 going on 30

Jennifer Garner’s rainbow dress in “13 Going on 30” is truly a fashion staple. I think everyone and their mother dreams of getting their hands on it.  Jenna (Garner) is sick of junior high and wishes she could be an adult already. All of a sudden her wish is granted and she’s 30 years old except life isn’t as grand as she expected. Who doesn’t love a plot where the character is in the wrong body or time period?

Sisterhood of the traveling pants

Blake Lively, Alexis Bledel, and America Ferrera. That’s it. That’s all I have to say. No, but seriously I don’t remember the last time we got this stacked of a female-led cast. This is a movie that has honestly become a generational staple. It follows 4 best friends all embarking on extremely different summers yet they all share this one pair of jeans that somehow fits them all perfectly. We go to Greece, South Carolina, Maryland, and Mexico but the story highlights the ultimate value of friendship.  

Bring it on

Oh to be a cheerleader in California. This is a feel-good movie about two feuding cheer squads. There’s drama, there’s dancing, and there’s a lot of badass female energy. I say it’s a solid favorite for the girls. Kirsten Dunst, Gabrielle Union, and Eliza Dushku star, and there’s no doubt that they shine. I could rewatch the cheer competition routines from the end over and over again. 

Princess Diaries

Before Anne Hathaway became the people’s princess, there was Mia Thermopolis. Hathaway plays a normal girl from San Francisco whose life completely flips around when she finds out she’s the princess of Genovia. We watch Mia go through the struggles of becoming royal and all the baggage it carries along with it. Julie Andrews shines of course as the queen of all queens. I think we are all still waiting to find out we are secretly princesses as well. 

Legally Blonde

Elle Woods is a household name at this point. When you think of girl power, I think “Legally Blonde.” Elle Woods (Reese Witherspoon) has everything she wants in life. The perfect clothes, the attractive boyfriend, and of course the sorority status. She is the girl everyone wants to be. All of a sudden her boyfriend dumps her calling her “too blonde” and the rest is history. Elle realizes she needs to show him that she can do more than that so she gets into Harvard Law. “What, like it’s hard?”


I’m still waiting for my talking starfish earrings. Aquamarine is every mermaid-obsessed girl’s favorite movie. Sara Paxton stars as Aquamarine in all her blonde and blue hair glory. Two teenage girls teach Aquamarine to live a normal human life which ends up being harder than they thought. Aquamarine just wants to show her dad that love is real and she finds that with a human. I’m forever longing for my “Island in the Sun” romantic dance scene.

Coyote ugly

Every girl and their mother watched “Coyote Ugly” and immediately booked their trips to NYC to go sing and dance on top of the high tops at a women’s run bar. This movie follows Violet (Piper Perabo), an aspiring singer who goes to NYC to pursue her dream. She ends up getting a job at a bar called Coyote Ugly where she befriends the “Coyotes” who work hard to make their money even if that means they have to entertain drunk guys. This is the perfect movie to watch with your girl gang. It screams women supporting women.

Hi! My name is Isabel Petrou. I am a current Sophomore studying Public Communication at The University of Vermont. I love reading, enhancing my style, going to the beach, and trying fun iced coffees from cute cafés. I am so excited to be a part of Her Campus and write articles that truly help college students make the most out of their time at school!