As a young girl, few things were more fun than a sleepover with your best friends. Laughing until you cry, making up sick dance moves, truth or dare, and stuffing your face with chips and ice cream was the life from about 2nd grade on until… well, to this very day! And don’t forget talking about boys, prank calling them, and envisioning your wedding day to your schoolyard crushes. Such innocence. Such fun.

When it gets down to it, what would a sleepover be without a great movie that will prematurely teach you about sex, make you scream your head off with laughter, fawn over the hot lead actors, make you all cry, or scare you all just a little bit? But you’re all sleeping in the same room, so it’s all good. Walking around Blockbuster with your girls spending an hour picking the perfect flick is such a fun memory for so many of us and the following movies were sure never to disappoint. Guaranteed you’ve probably watched all of these with your friends during the ’90s and early aughts. So, take a walk with me down memory lane and relive simpler times of teenage move nights and sleepover fun.

24. The Craft (1996)

Light as a feather, stiff as a board… we all definitely tried to make our friends float with our own incantations and swore they rose at least half an inch! The Craft introduced us to three teenage witches and the new girl who joins their coven. They use their spells to get boys and get back at classmates. Genius! Fairuza Balk terrified you all when she takes her witchcraft a little too far, but it was a fantastic film all the same. We all watched this before we were old enough (don’t lie!), so the first viewing was always a little intense. But that only means it keeps getting better after that.

23. How to Lose a Guy in 10 Days (2004)

This is the ultimate rom-com, thus making it the most perfect sleepover movie. Kate Hudson‘s Andie is a women’s magazine writer tasked with doing an article on how to lose a guy in ten days basically by making classic relationship mistakes. Got it? Matthew McConaughey plays an ad exec who makes a bet that he can get a girl to fall in love with him in ten days. See where this is going? Kate Hudson and Matthew McConaughey have great chemistry and this movie can be watched over and over. And it was.

22. Cruel Intentions (1999)

This movie definitely taught you about sex and drugs and you also probably lied to your parents about what the sleepover movie when Cruel Intentions was the pick. It was fascinating and disturbing, all at the same time. Sarah Michelle Gellar plays a mean Manhattan prep schooler who uses girls for revenge. She’s also got a strange relationship with her step-brother, played by Ryan Philppe, who’s trying to sleep with her. Reese Witherspoon and Selma Blair also star. There’s young love, sex, cocaine, and backstabbing. Sleepover movie for sure! As long as your parents don’t walk in!

21. Sugar & Spice (2001)

A classic high school film telling the tale of high school cheerleaders pulling off a series of bank robberies. Kind of like the early ’00s version of Spring Breakers. Except in this one the crime-spree is for good cause. The head cheerleader is pregnant and they help her get the money she needs for the baby by stealing it… like good friends do. It’s unbelieavble and corny but super fun and great for a laugh.

20. Mean Girls (2004)

Of course you’ve seen Mean Girls and who better to watch it with than with your sleepover squad? Lindsay Lohan was the teen queen and the plastics were so fetch! We’ve all seen these movie about 1000 times, can quote every line and it is the quintessential pop culture reference, but it never fails to make us laugh or provide quality entertainment. Definitely a quotable sleepover favorite!

19. Clueless (1995)

Clueless is and will forever be an amazing film. This 90s teen classic shows us the rich kids of Beverly Hills before the reality show, and in much more hilarious way. Cher is pretty, popular, and starts trying to do good deeds for others in her life. Things don’t go as planned (does it ever in a sleepover movie?), but it’s fun watching her antics. We’ll probably never get over the fact that she falls in love with her ex-step brother, which just seems a bit weird, but anything for a young Paul Rudd, I guess.

18. She’s the Man (2006)

Remember when Amanda Bynes was the best and would do anything to give us a good laugh? We miss her. Here, she plays a twin who poses as her twin brother so she can play soccer at an elite school after the girls’ team at her own is cut. Channing Tatum plays the hot soccer team captain in one of his earliest roles which is a bonus. Another bonus: his shirtless scenes. This movie seriously has you rolling with laughter from beginning to end with all of Amanda’s classic mannerisms. What better way to spend a slumber party?

17. 13 Going on 30 (2004)

TBH being 13 was really hard at times and this movie made you forget your troubles of being an awkward teen girl. Jenna Rink is humiliated on her 13th birthday, desperate to be popular, and wishes to be 30, flirty and thriving, like the grown woman on the cover of her favorite magazine. Anyway, she wakes up the next morning, as an actual 30-year-old Jennifer Garner, though still a young teen on the inside. Needless to say, being 30 isn’t all it’s cracked up to be — especially because things with her BFF, Matty, are far from perfect.

16. The Holiday (2006)

So, home-exchange is definitely a thing and it’s not sketchy at all? And of course, everyone falls in love in the holidays. British Iris (Kate Winslet) is down in the dumps because her co-worker, whom she loves, is marrying another woman. He’s also totally stringing her along as a backup plan. Amanda’s (Cameron Diaz) BF is cheating on her, and she can’t deal (or cry) because she’s emotionally unavailable. Logically, they both opt for a holiday vacay and think the most stress-free way of doing so is by switching homes with a stranger. It’s the perfect movie for hopeless romantics — especially during the Christmastime — but when it came to all the teenagers watching it, Kate Winslet’s character was the only one super relatable. Unrequited love? Yeah, we been there, girl.

15. Coyote Ugly (2000)

A struggling songwriter moves to the city and works at the famous Coyote Ugly bar where all the bartenders are hot women with attitudes. This songwriter meets a cute guy (duh!), struggles with her new city life (yep!), and tries to get her big break as a singer/songwriter. How she struggles for so long is beyond me because, “Can’t Fight the Moonlight” and “The Right Kind of Wrong” are fabulous songs that would have you and your friends dancing all over the place. Coyote Ugly was like sleepover karaoke.

14. Legally Blonde (2001)

Legally Blonde is the ulitmate chick flick that inspired all of us to be lawyers and go to Harvard (until we realized it was really hard), but it also gave us the “bend and snap” pick up move which was the perfect thing to practice at a sleepover! Who better than your best girlfriends to help you perfect your new signature move for pickin’ up guys? Did it actually work? Did anyone ever do it? Who knows… but it was fun! Reese Witherspoon was perfect as the empowering Elle Woods and has no doubt graced countless sleepovers as the main movie entertainment for the night.

13. Final Destination (2000)

This movie was absolutely terrifying. You escape death just to be killed in the most horrific way?!?!?! Literally, WTF. A PG-13 horror movie, plus 90s hottie Devon Sawa, all the ingredients to make this scary flick a sleepover staple. It was gory, surprising, and definitely got in your head. At least after watching you didn’t have to sleep alone. This franchise is probably 90% of the reason our generation is terrified of a tanning booth. Final Destination, you know, and the 1000000 other reasons not to use a tanning booth.

12. Bring It On (2000)

Nothing riles up a group of girls at sleepover like a cheerleading competition movie, especially one as well done as Bring It On. Kirsten Dunst stars as a cheer squad captain in Torrance, California who learns that the graduating senior stole their routine from the Compton squad, and they’re are not happy about it. It’s cheer crisis that leads to a major cheer off. There’s also lots of fun cheers, music, and it’s just an awesome movie celebrating female friendship, but you already know that. What you might not have noticed at that age is that this sleepover movie is kind of like a crash course in cultural appropriation. Definitely makes it worth a re-watch, no?

11. Step-Up (2006)

Gotta have the movie that gave us a sexy Channing Tatum and some A+ dance moves. He’s an American treasure and dances like a god. He plays a wrong-side-of-the-tracks boy who’s paired with a privleged dancer in a showcase, played by his future wife Jenna Dewan-Tatum. Step Up is a super seductive dance movie that no doubt made you squeal and stare in that prepubescent stage. What’s more fun than a dance battle? The answer is nothing. Nothing beats a good old fashion dance battle.

10. Sleepover (2004)

Uh… duh, you used to watch Sleepover at your sleepovers. How could you not? Four teen girls spend the last night of junior high doing a sleepover scavenger hunt against the popular girls for control of the cool lunch table in high school. Winning plot. Plus, did you realize a young Evan Peters played the goofy skater kid who helped the girls out for a little bit? This movie is junior high in a bottle. Treasure it.

9. How to Deal (2003)

Mandy Moore has impressed us with her acting and her singing since pretty much the beginning of time. We’re not the only ones obsessed with This is Us, I’m sure. But long before the prime time drama, Mandy was playing the skeptical schoolgirl in How to Deal. This movie was definitely a bit more of an emotional sleepover film, dealing with death, divorce and teen pregnancy but sometimes you need an engaging movie that will make you all cry together.

8. 10 Things I Hate About You (1999)

Based on the Shakespeare play The Taming of the Shrew, 10 Things I Hate About You is a smart, genuinely funny teen comedy. When popular Bianca wants to date, her father makes the rule that she only can once her anti-social (and TBH, super mean but in a lovable way) older sister, Kat, starts dating. Thus beginning a teenage scheme involving the nerdy-but-nice boy who wants to date Bianca, the other guy that wants to date Bianca, and the bad boy who is paid to date Kat (or try to) played by the late, great Heath Ledger.

7. Miss Congeniality (2000)

When you re-watch this sleepover movie as an adult, it’s pretty hard to ignore how crazy is actually is — not that it makes it any less enjoyable. The plot follows a tough tomboy detective who goes undercover at a beauty pageant to intercept a bomb threat by a domestic terrorist. It’s some pretty serious stuff, but has a lot of humor, the extremely likeable Sandra Bullock and a great makeover montage. Sleepover movie win for sure.

6. Drop Dead Gorgeous (1999)

This dark comedy stars Kisten Dunst in one of her funniest and best roles as a poor, sweet pageant contestant in Minnesota where all of the contestants start dying one by one in mysterious ways. Denise Richard‘s mean, rich girl character seems to be behind it, but who knows? Even knowing the ending didn’t stop us for watching Drop Dead Gorgeous on repeat. This movie is so funny, witty, ridiculous, and full of crazy characters with insanely funny pageant stereotypes.

5. Save the Last Dance (2001)

Is there a single dance movie in history that it’s iconic in its own right? We’re convinced that the perfect sleepover movie has a little bit of tragedy, hardships, a love story, and a lot of dancing. Save the Last Dance has all of these, plus the essential charm. Julia Stiles stars as a teen ballet dancer who loses her mother in car accident and moves in with her dad in inner city Chicago. There, she meets a new crowd and learns a new style of dance: hip hop. She also falls in love. (Natch.)

4. A Walk to Remember (2002)

I really can’t think of a better sleepover movie than A Walk to Remember. There might not be much dancing, but there’s two parts tragedy to make up for it. Mandy Moore (a staple of teen movie nights) is the unpopular ministers’s daughter, forced into a tutor-student type scenario with the popular boy played by Shane West. If you haven’t seen this one (and at this point… HOW?!?!?), we don’t want to spoil the twist. Just know you’ll finish this movie with absolutely no tears left.

3. Now and Then (1995)

A killer sound track, coupled with the love and innocence of young friendship makes for not only a perfect sleepover, but a perfect teen chick flick that sticks with you for life. Now and Then brings us to the 1970s, telling the story of four best friends and of the summer when they were 13. They’re earning money for a treehouse and practicing seances in graveyward. Typical stuff. This movie explores what happens to your childhood friendships when you grow up… Cue all the promises to “not let that happen to us,” made by teenage girls after watching this sleepover movie.

2. The Princess Diaries (2001)

Wouldn’t it be cool to wake up and find out you’re a princess? If it hasn’t happened by now, it probably won’t ever happen, so, sorry. But it was fun watching nerdy and awkward Anne Hathaway go from frumpy and awkward to popular and awkward. It’s definitely messed up how all they really did to make her princess beautiful is straighten her hair, take off her glasses, and tweeze the brows (thus showing its age because power brows are in RN), but it’s a movie and that’s classic, so whatever.

1. Sweet Home Alabama (2002)

Reese Witherspoon is a go-to gal for the classic rom-com, and pretty much felt like another member of the clique since she was so often featured during our sleepovers. Sweet Home Alabama is one of the best films from the romantic-comedy heyday of the early 2000s. Reese plays a New York socialite who beomes engaged to the most perfect rich man (I wish) but she first must travel home to her small southern town to… wait for it… officially divorce her equally sexy high school sweetheart. YES. You probably know what happens but watch it again to relive all those feels.

LEAVE A REPLY

Please enter your comment!
Please enter your name here