Oh, sleepovers. Nothing is better than spending a night with your bestfriends overdosing on junk food, laying around in your most comfortable and embarrassing pajamas and watching five movies in a row. Sleepovers can either be extremely relaxing or hard to recover from, but they are so funny and irreplaceable that I personally think there should be an international Sleepover Night. 

Movies, obviously, are a must-be according to the Sleepover Bible (made up by me right now), but sometimes it can be hard to choose what to watch. I guess one of the best ways to decide is having a marathon or establishing a theme: you can watch the whole Harry Potter/Pirates of the Caribbean/Star Wars saga, go for a tv series like Friends or Grey’s Anatomy or follow a fil rouge that links together a few films.

What I’m proposing you today is one of my favourite themes: teen movies from 1990 to 2000. Beside being extremely funny and unmissable if you are a movie amateur, they definitely left a mark in the filmmaking history, defining a generation not so far in time from ours. They can also teach you something about style or pop culture, so you have no excuses left not to watch them!

JAWBREAKER (1999)

People worshipped them and cursed them, but everybody wanted to be them .

In Jawbreaker you have all the ingredients for a classic teen movie: a high school, a popular and mean clique of Queen Bees, a kind-hearted girl loved by everyone, a prom, hot guys - with the only exception that this is not a classic teen movie.

Jawbreaker is a dark comedy and (surprise!) it involves a kidnapping, a death and police investigations. Written and directed by David Stein, the movie revolves around the “Flawless Four” of Reagan High School, Los Angeles:  Courtney Shayne, Marcie Fox, Julie Freeman and Elizabeth Purr. They all rule the school with a terror regime, except for Liz. She is not as mean as her friends and makes no differences in relating with others - her beauty and honesty, then, make her the most loved and admired girl. 

Obviously, this generates jealousy in Courtney, Marcie and Julie, who decide to prank their friend on seventeenth birthday, by performing a fake kidnapping. They take her off guard early in the morning, binding her with ropes and pushing a jawbreaker candy into her mouth. The girls lock Elizabeth in the trunk of a car and drive towards the mall to celebrate their friend’s brithday with breakfast. However, once they open the trunk, the sight is definitely not what they expected it to be…

Jawbreaker is worth watching not only for the twisted, surprising plot and the iconic (and definitely realistic) language used by the girls, but also because it explores the dynamics of a group of girls with the voice of an outsider, Fern Mayo, who finds herself involved in the events against her will. This movie is gonna make you laugh, startle and maybe regret not living in 1999.

Cruel Intentions (1999)

In the game of seduction there’s only one rule: never fall in love.

Drugs, sex, a hot step-brother, games of seduction, classy and total black outfits, rich mansions. If you like this list, Cruel Intentions is the perfect movie for you. Beside having an incredibly attractive cast, a young Reese Witherspoon included, its plot twists the usual “mean clique” dynamics.

Set in a wealthy Manhattan, the film is about an oddly assorted couple: Sebastian Valmont and his step-sister Kathryn Merteuil. He’s well known for his countless sexual conquers and seductive manners, which perfectly match Kathryn’s inner wickedness and malice - but they always both manage to get away with it thanks to their fascinating looks and charming attitudes. 

The tight relationship between the two not only sees them accomplices in many misdeeds, but also gives rise to explicit sexual innuendos, as Sebastian’s not-so-secret fantasy is to sleep with Kathryn. Despite wishing the same, the girl likes to play it hard to get, so she decides to set up a bet: if Sebastian will be able to seduce Annette Hargrove, Kathryn will have sex with him - otherwise, she’ll get his vintage Jaguar. It’s not as easy as it seems: Annette is the daughter of their school’s headmaster and has recently written an article on saving her virginity for marriage.

As the time goes by and the relationship with Annette develops, Sebastian will find his controversial morals hardly tested. He’ll also have to manage the seduction of the young and naive Cecile, the new girlfriend of Kathryn’s ex, and he’ll be soon torn between his usual lifestyle and a wager maybe too hard to win, even for his unbeaten ego.

Cruel Intentions is weird, explicit, somehow shocking. It points out the differences between boys and girls as it comes to sex, providing a few interesting reflections under a chic, witty and dark atmosphere. Kathryn’s outfits are ICONIC and the movie will make you want more - and you’re lucky, because there are a prequel and a sequel.

Clueless (1995)

Dear diary, I’m more fabulous than five minutes ago.

I don’t even know how to start with this and if you’ve never seen Clueless before… oh my gosh, you can’t imagine what you’ve missed. This movie is p-e-r-f-e-c-t! 

Yes, we have a Queen Bee, Cher, with her sidekick Dionne. And yes, she’s vain and superficial. But she is funny, gorgeous, good natured, harmless and extremely relatable. You could easily make any quote from her character yours, really. She’s crazy wealthy and lives in a mansion in Beverly Hills, obviously being the most popular girl at school.

The movie explores Cher’s life and her attempts at making “good deeds”, showing how her attitude is more innocent than biased. She decides to give Tai Frasier, a “tragically unhip” girl, a makeover aimed at initiating her into the popular universe of their high school; she tries to act as cupid and match two professors (also to raise her grades); all of this, just for the sake of “giving back to the community”.

Cher’s hilarious adventures continue as she finds herself facing a new, attractive boy at school, her annoying stepbrother, the driving license exam and other teenage things we’ve all been through. I loved this movie because she’s fierce and self confident in a positive way, for once - and I won’t even mention the outfits of almost every character, which I’ve seen more than once reinterpreted in the latest collections of many fashion brands. And let me add that Alicia Silverstone’s facial expressions are the best thing in the world… In a few words: watch it. You won’t absolutely regret it.

The Craft (1996)

“You girls watch out for those weirdos” - “We are the weirdos, mister”

Everyone loves a bit of magic. Candles, chanting odd words, summoning the supernatural, meeting in the middle of the night - all things you probably don’t do but that still sound fascinating and attractive, especially if you are a young girl with a mysterious past in a new school where you know no one.

This is how it goes for Sarah Bailey once she arrives to the catholic academy of St. Benedict, Los Angeles. A group of outcasts, with difficult, gloomy lives and rumored to be practicing witchcraft, notices that Sarah is not as normal as she seems, thus luring her into joining their coven. The powers of the four girls reach a whole new level as they try to fix their messy lives and make up for any wrong that had been unfairly done to them.

However, nothing is easy when it comes to unearthly powers - the group will face difficult personal struggles and they will soon understand that everything comes with a price. 

This thriller will open your eyes on the hard life of social rejects in a surreal way, making you think twice before exposing someone not as lucky as you - you never know what may be their revenge. I loved The Craft because it explores a different side of the world depicted in the movies listed above - it gives voice to the unheard and shows things from a different point of view.

10 Things I Hate About You (1999)

But mostly, I hate the way I don’t hate you, not even close.

Sisters can be so different. Take Bianca and Kat Stratford, for example. One is popular, beautiful, admired and elegant, the other is a smart, casual, ironic bookworm. Cameron James (and adorable Joseph Gordon-Levitt) is head over heels for Bianca as soon as he sees her, but he’s warned by a friend that the girl’s father doesn’t allow her to date anyone. This doesn’t only upset Cameron, but Bianca as well - that’s why before the prom she quarrels with her dad until he agrees on letting her go at one condition: Kat has to find a boyfriend and go to the prom, too, causing Bianca to become furious since her sister will never want to be with someone.

Cameron finds out about the new rule and decides to find a boy who will date Kat, so then he’ll be able to go out with Bianca. The mission seems impossible, but of course we have Heath Ledger, in the role of Patrick Verona, who once again becomes the hero and (obviously with a heavy salary) agrees on trying.

Will the mission stay professional? Will Kat resist to Patrick’s charm or will she be trapped by the good-looking outcast as bitter as she is? Will Bianca go to prom with Cameron? You need to watch the movie to find out. This is one of my favourite ones, I’ve seen it at least three times and it’s just great - I always like watching the development of a romantic relationship, because each one is different from the other. And the singing scene on the bleachers? Iconic.

Romeo + Juliet (1996) - trailer

If love be rough with you, be rough with love.

Do I even have to say something?? I mean, Leo DiCaprio, Shakespeare’s most known masterpiece, love and death, Baz Luhrmann. This is enough, isn’t it?

Romeo + Juliet is the modernized and adapted version of the famous, tragic love story. It’s visionary, surreal, heartbreaking and it should be seen at least once a week because it’s just too much. It is set in a imaginary Verona Beach, where the adventures and deeds of two families in war intertwine with the forbidden love affair of a young boy and girl. The plot follows Shakespeare’s script, but you won’t find swords or horses. Guns and sportscars, gas stations and a swimming pool are just a few of the innovative twists Luhrmann has used in this dreamy and loud film.



What about you? What are your favourite 90ies/sleepover movies? Let us know by commenting this post, the Facebook page or sending an ask! x