Sleepover 90s Comedy Movies: My Top 5

I very rarely sit down by myself to watch a film; I often find that if I’m alone, I don’t have the attention span. I’m always checking my phone, sending a tweet, or catching up with group messages that seem to ping every second of the day. I prefer watching films during nights in with the girls – 90s sleepover style. I love getting all cosy in my pyjamas, grabbing some pizza or nibbles, and sitting down with my friends for a good old giggle. Comedy is definitely my preferred genre – I get scared very easily, so horror films are out of the question (to the dismay of many an ex-boyfriend). I also hate violence and can’t deal with blood or gore, so most action films are a no-go for me. I can’t stand watching sad films, nor ones with particularly complex plots; my general reasoning for watching a film in the first place is to be entertained without having to think about it too much! There are so many good comedies available to watch with the girls – so where do you start? I’m a sucker for the classics, and I’ve listed my top 5 from the 90s below. You may have well seen most (or even all) of them; but these are so good, I can watch them a million times over!

1. 10 Things I Hate About You (1999)

“10 Things I Hate About You” has every piece of the puzzle in terms of creating the perfect romantic comedy; a simple plot, relatable characters, and a few famous faces! An adaptation of Shakespeare’s “The Taming of the Shrew”, the plot follows the adorable Joseph Gordon-Levitt as he tries to win the heart of Larisa Oleynik. His main obstacle? Her father’s rule that she can only date if her unapproachable sister (played by Julia Stiles) does. Cue a plan involving Heath Ledger, a bad boy in Andrew Keegan, plus a lot of Shakespeare references – and you have a whole lot of drama!

2. Clueless (1995)

The cast of “Clueless” surely deserve an award for the cast to have aged the least in the past 20 years! This was one of the first girlie comedy films I ever watched at a sleepover – and it’s still a favourite of mine to this day. Alicia Silverstone plays a privileged 16 year old in California who doesn’t take an interest in the guys at her school – but she’s certainly popular with them! As well as struggling with teenage romance, she also takes new kid Brittany Murphy under her wing with the help of best friend Stacey Dash, whilst arguing with ex-stepbrother Paul Rudd (who literally hasn’t aged a day). This film inspired a lot of the fashion choices of the mid-90s – and you might have seen them recreated in Iggy Azalea’s homage to the film for her track “Fancy”.

3. Never Been Kissed (1999)

Drew Barrymore has been a favourite actress of mine for a number of years, and this is one of her best comedic performances in my opinion. She plays Josie, a dull copy editor looking for her journalistic big break. She gets the opportunity to go back to school undercover for a huge article – but her experience in high school first time round wasn’t exactly pleasant. She has help from her brother David Arquette, is befriended by school nerd LeeLee Sobieski and develops a crush on teacher Michael Vartan. Will her cover be blown, or will she get her story?

4. She’s All That (1999)

The best films in romantic comedy involve some sort of makeover (Miss Congeniality anyone?) and this one is no exception – even being the main basis for parody “Not Another Teen Movie”. Freddie Prinze Jr is the most popular guy in high school – but then he’s publicly dumped by his queen bee girlfriend. Claiming he can turn any girl in school into the prom queen, his friends present him with a bet – in the form of Rachael Leigh Cook, a nerdy student with a passion for art. But as he spends more time with her, his conscience starts to get in the way of his pride! Matthew Lillard is fantastic as the comedic new boyfriend of the queen bee, while Paul Walker plays the bad boy orchestrating the bet.

5. The Wedding Singer (1998)

I could watch this film all day long, even just for the incredible soundtrack! Set in 1985, Adam Sandler is the town’s best wedding singer – with his own wedding imminent. Drew Barrymore has arrived in town with her rich fiancé (Matthew Glave) and the two become friends – but with his engagement to Angela Featherstone in ruins and her fiancé not being as perfect as he seems, can the pair admit that they have feelings for each other before it’s too late? This film will have you in stitches – and watch out for the cameo from Billy Idol!

That concludes my top 5 90s comedy sleepover films – is your favourite on the list? Let me know in the comments!