10 Must-Watch Movies from the 2000s That Defined a Generation

I have an undying love for movies, especially the ones I grew up with. The 2000s shaped me into the fabulous thirty-year-old girlie I am today, and I owe a lot of that to the iconic films of the era. My love for movies runs so deep that my sister and I even started a podcast where we recap our favorite childhood classics—shameless plug, but go check out Please Don’t Spoil the Movie, available everywhere you get your podcasts!

I like to think of myself as a bit of a 2000s movie expert (self-appointed, of course), and I firmly believe these films have stood the test of time. They’re the kind of movies that will continue to be loved, quoted, and rewatched for generations to come. But if you need a place to start, I’ve got you covered! Here are ten absolute bangers that shaped an entire generation of girlies.

1. Bring it On

Kicking things off with a movie so iconic it spawned six sequels, Bring It On! On the surface, it’s about two high school cheerleading teams battling it out for a national championship, but it’s so much more than that. This film dives into cultural appropriation, feminism, and classism, all while showcasing some kick-ass cheer moves. Talk about a cinematic masterpiece!

2. Mean Girls

On to another great American classic, Mean Girls. I honestly can’t imagine a person who hasn’t heard about this iconic film. But just in case… Mean Girls follows Cady Heron played by the amazing Lindsay Lohan as she navigates the wild world of American high school after growing up homeschooled in South Africa. She is deeply unfamiliar with the girl rules of American high school but soon rises to the ranks only to fall from grace when she files a little too close to the sun (aka popularity). This film is a perfect reminder that high school is basically survival of the fittest, especially for girls.

3. Legally Blonde

Stepping into the ultimate realm of girl power, we have the unexpectedly motivational chick flick, Legally Blonde! Elle Woods had her future all planned out: marry rich, live the dream as a stay-at-home wife, and be effortlessly fabulous. But when her boyfriend breaks up with her for not meeting his "serious" Harvard Law aesthetic, Elle takes her life into her own hands and gets into Harvard Law. Legally Blonde is the perfect reminder that you can do anything when you set your mind to it… especially if it means proving a man wrong!

4. She’s the Man

I can’t talk about movies from the 2000s without mentioning an Amanda Bynes classic and one of my absolute favorites, She’s The Man. She’s the Man is loosely inspired by Shakespeare’s Twelfth Night, so you know it’s going to be good. This movie follows Viola Hastings as she disguises herself as her twin brother to play on the boys' soccer team. Chaos, comedy, and awkward encounters ensue, all thanks to Amanda Bynes’ absolutely hilarious performance. It’s no surprise this film has a cult following.

5. John Tucker Must Die

There’s no plot I love more than one that involves ruining a man. And if that is something that interests you then John Tucker Must Day is the perfect movie for you. When a group of girls from different cliques discovers they’ve all been played by the same ultra-popular John Tucker, they band together to ruin his life. Because honestly, nothing brings women together like seeking revenge on a man who did them all dirty. John Tucker Must Die is the ultimate reminder that sometimes, karma just needs a little extra push.

6. The Princess Diaries

Everyone loves a fairy tale ending but if you want one that doesn’t fully revolve around a man, then Princess Diaries is the movie for you. Shy and awkward Mia Thermopolis is thrown for a loop when she learns that she is actually royalty. This movie had me hoping that one day I would wake up to discover that I was secretly a princess. But for Mia is just another reason for her to be bullied and be called a freak. In the end, Mia embraces her crown (because, honestly, who wouldn’t?) and discovers that true royalty isn’t just about tiaras and ball gowns but it’s about finding confidence in yourself.

7. A Cinderella Story

Speaking of fairy tale endings, A Cinderella Story starring Hilary Duff is a modern twist on the classic tale. Sam, who has spent most of her life being bossed around by her evil stepmother and stepsisters, takes a chance on love when she agrees to meet her mysterious secret pen pal. In the end, though, Sam chooses to put herself first, breaking free from her toxic family and chasing her dream of starting fresh at Princeton. Because sometimes, the real happily ever after is choosing yourself…and having a man on your arm is a small bonus.

8. Easy A

If there’s one thing that can get a group of high schoolers fired up it’s a juicy rumor. And no movie captures the messiness of the rumor mill like Easy A. Olive Penderghast, a smart and witty high schooler becomes the center of scandal after a little white lie about her virginity spirals out of control. Instead of shutting down the lies, she leans into her new bad girl image and even starts rocking a bright red ‘A’ on her clothes. But in the end, Olive sets the record straight and realizes that the only opinion that truly matters is her own.

Want to relive all the drama? Check out our latest episode, where my sister and I recap Easy A!

9. Step Up

If you love perfectly choreographed dance numbers and bad boys then Step Up is the movie for you. When rebellious street dancer Tyler Gage finds himself doing community service at a preppy arts school, he crosses paths with Nora, a passionate ballet dancer in need of a new dancing partner. Despite their differences, their shared love of dance brings them together as they push each other to step outside their comfort zones. Step Up isn’t just about incredible choreography it also teaches us the importance of taking chances, and chasing your dreams.

10. Save the Last Dance

And I can’t talk about worlds colliding through the beauty of dance without talking about Save the Last Dance. After the tragic loss of her mother, aspiring ballerina Sara moves to a new school in Chicago, where she struggles to fit in. But when she meets Derek, a talented hip-hop dancer who helps her rediscover her passion, their connection sparks more than just a little one-two step. And while Sara’s questionable final dance routine somehow lands her a spot at Juilliard, Save the Last Dance reminds us that stepping outside your comfort zone can lead to incredible possibilities.

Whether you grew up with these movies or are just discovering them now, there’s no denying the impact they had on an entire generation of girlies. From iconic one-liners to unforgettable dance numbers and legendary teen drama, 2000s movies truly understood us. So, if you’re in the mood for a nostalgia trip, grab some popcorn, queue up these classics, and let yourself be transported back to a pure time of flip phones, low-rise jeans, and peak teen cinema.