The Best Sleepover Movies Of All Time, Ranked By Early 2000s Aficionados

What is it with teen movies and rom-coms romanticizing jobs in media? Anyway, watching Drew Barrymore portray a Chicago Sun-Times writer portraying a high school student was a favorite for us all. Besides, David Arquette had to make an appearance in this list somewhere or it just wouldn’t be right.

God, this movie was SO FUN. It was my first introduction to Rob Schneider, Anna Faris, and Rachel McAdams, but it had some familiar faces too — Tia and Tamera, the real-life sisters I grew up watching on Sister, Sister. This movie gets to the heart of female friendship and crushes and being an awkward high schooler.

My friends and I dreamed of growing up to sing karaoke in dive bars, wearing little cut-up crop tops, just like Britney did as Lucy in this movie. Honestly, this was kind of like an early Sex and the City, where we all identified with one character or another (I wanted to be a Mimi so badly). Kim Cattrall playing Lucy’s mom has nothing to do with it.

Cry Baby came out in 1990, but it was still a fixture at all the early 2000s sleepovers I attended. While it definitely checks the “fantasy of falling for a bad boy who changes for you” box, it felt like a more theatrical choice than your average teen movie.

Watching Nick Cannon through a 2025 lens feels weird now, but at the time, this movie was a gem. It’s a riff on the classic storyline of popular-girl-gets-stuck-in-arranged-dating-with-the-nerd, but I dunno, something about it kept us coming back.

Should we have been watching it? No. Did that stop us? Also no. This movie kicked off a massive franchise of scary movie parodies, and Anna Faris was brilliant in every iteration. This felt like one of the first movies we got our hands on that was an “If you hear my mom coming, turn it off!” type of experience.

Piper Perabo singing “Can’t Fight The Moonlight” is seared into my DNA, and my sister and I would belt out the LeAnn Rimes version in the car like, all the time. It scratches that itch of teenagerhood where you wonder what it would be like to drop out, run away, and start a new life doing something crazy your parents would hate.

Is there anyone who didn’t want Drew Barrymore’s dress from this scene?! This retelling of Cinderella was perfectly timed for those of us who had loved the animated Disney version but were ready to grow it up a little. Plus, Prince Henry was peak ‘90s dreamboat material.

Heath Ledger made his mark on many a teenage heart in this movie, and honestly, just as many of us girls fell in love with Julia Stiles. Kat Stratford was an idol to those of us who were perfectly fine being the unpopular girl who did the assigned reading (and took no prisoners while she was at it). Come to think of it, is this movie why we’re all obsessed with enemies-to-lovers books now?

Drop Dead Gorgeous is one of the most under-appreciated 2000s teen movies, in my opinion. The cast is full of heavy-hitters, and as Jia Tolentino so expertly put it for The New Yorker, the movie gets “that being a teenage girl is, in fact, deranged and dehumanizing and frequently unsubtle.” That said, it’s rife with stereotypes and offensive portrayals of marginalized groups, so maybe watch it with your teen on their first screening.

Whom among us didn’t learn the opening choreo to this movie with their best friend and perform it ad nauseam along with Kirsten Dunst? Bring It On was always on at my childhood best friend’s house, and when I think of iconic 2000s teen movies, it’s one of the first that comes to mind.

Somehow, Now & Then never made it into my household — every time I watched it was at a friend’s house. So, this classic is firmly cemented as a sleepover movie for me. The cast is star-studded, the spooky-factor is there, and the message of how friendships grow and change always felt extra poignant when watching it with your own BFFs.

Listen, I adore every single movie on this list, but no film does it all quite like 13 Going On 30. It’s got a little bit of magic, lots of nostalgia, a coming-of-age story, the idealized magazine editor career, and the chic city apartment. It has every single element you could want from a slumber party movie,