What is the best high school movie? How long is a piece of string?

The best teen movie is a question so steeped in personal preference that it’s impossible to answer objectively. One woman’s Clueless is another’s Easy A. For some, a perfect high school movie is about partying, hijinks and having a good time. (Might we suggest Booksmart?) For others, they want romance, melodrama and doodling in notebooks. (Pretty In Pink or 10 Things I Hate About You is our drug of choice when we’re in that particular mood.)

Teen movies thrive in specificity – the devil is entirely in the details, things like Andie’s handsewn prom dress in Pretty in Pink, or all those bottles of Yakult in To All The Boys I’ve Loved Before. 

But what makes a teen movie sing is that even if you weren’t choosing plaid outfits from your computerised closet in the Nineties like Cher Horowitz, or even if you weren’t football mad like Jesminda and Jools in Bend it Like Beckham, everyone went through adolescence and almost everyone had the experience of going to a high school. The minutae might shift but the message of the agony and ecstasy of being a teenager is the same, no matter the setting. 

We’ve all been in Laney from She’s All That’s shoes. We’ve all fallen for Danny Zucko, the bad boy with a heart of gold. We’ve all had to work on ourselves, like Torrance did in Bring It On. We’ve all struggled through the low moments of adolescence, like Josephine in Looking For Alibrandi. (If you haven’t heard of the latter, it is a very popular Australian teen movie that deserves your love and affection about the perils of Catholic high school, big Italian families and falling in love.) 

We have all been there. And that’s the power of watching a smart, well-made high school movie. It validates the feelings and emotions and concerns of young people and reflects their experiences back at them. It tells them that what they are going through is normal. And, if you’re really lucky, it reminds them that everything is going to be alright.

So, what are some of the teen movies that shaped our lives and are well worth a re-watch, even as as a grownup? 

Bend it like Beckham – Sarah Shaffi, writer 

As a teenager, there weren’t many Hollywood films that featured Asian teenagers (there still aren’t), so Bend It Like Beckham was a revelation. Yes, people remember this film as being Kiera Knightley’s break-out role, but Parminder Nagra is the true star. She brilliantly portrays a teenager trying to navigate two cultures, as well as a crush on the then swoon-worthy Jonathan Rhys Meyers, the embodiment of the early 2000s teenage dream. Yes, it’s a little dated now, but I will always love Bend It Like Beckham for showing someone a little like me on the big screen.

Mean Girls – Fliss Thistlethwaite, Digital Executive Editor

If October 3rd means anything to you, we can be friends. Mean Girls is an iconic coming-of-age movie that, undeniably, shaped my teenage life. Although I might not have liked Regina George as a character, I certainly threw myself into dressing like her. Yes, I had a velour tracksuit (tell me who didn’t in 2004). Yes, I wore colourful vests, but stopped short of cutting out boob holes. And, yes, I’ve asked myself if butter is a carb. (It’s not, FYI.) And in non-Regina George related news, I’ve shouted “You go Glenn Coco” at friends, colleagues, runners on the street at least 17,453 times this year.

As I get older and wiser, I catch other character traits from the characters in the movie slipping into my every day. I proactively think about being the ‘Cool Mum’, not the ‘Regular Mum’ – get me a camera, a child and a Christmas nativity, and watch my transformation.

The best thing I learnt from Mean Girls is moral standing. I mean, not so much shouting “they don’t even go here” at people, but following the now-famous Cady ‘mathletes’ epiphany mantra.

“Calling someone stupid doesn’t make you any smarter. All you can do in life is try to solve the problem in front of you.”

Anyway, I digress. Can I get you guys anything? Some snacks? A condom? Let me know!

Clueless – Megan Murray, writer 

Clueless was just…glorious to me as a teenager. Alicia Silverstone’s perfectly flippy blonde hair had me yearning for a similar style, her penchant for fluffy pens is still affecting my stationery choices (my colleagues can attest to this – I’m always the only one wielding a sparkly, pom-pom-ended scribe in meetings) and every single damn fashion choice made an immortal mark on my wardrobe, and fashion forever. The beret, the matching sets, the sheer Calvin Klein slip dress with casual shirt thrown on top – this film has outfit inspiration for any occasion.

But, undoubtedly, the best thing about Clueless was that all of this glamour and gloss was simply for show, satirical really. Cher’s purpose in this film had nothing to do with wearing cute clothes or being popular, it was to teach teenagers several important lessons; always be true to yourself and don’t copy everyone else (shown in Cher’s refusal to give up her virginity because everyone else is), chicks over dicks every time (ew Elton!) and friendship is the most important thing. Period. 

I believed it all to be true then, and I still do now. Clueless, I’m like totally in love with you, even after all these years. 

13 Going on 30 – Meena Alexander, Sub Editor 

Like most teens, I was pretty self-obsessed. So imagine my delight when I saw this film for the first time and realised that it was all about ME. Just like Jenna Rink, I too wanted to escape suburban school life and become a high-flying magazine editor in Manhattan! I too dreamed of waking up in a £5 million Fifth Avenue apartment chock-full of Manolo Blahniks! I too was desperate to be 30, flirty and thriving!

I thought 13 Going On 30 would be my manual to obtaining all the things I so desperately desired, but instead it delivered some timely home truths: don’t be in a rush to grow up, because adult life is complicated – and a bag of magic wishing dust is the only way anyone in publishing can afford that many shoes. 

Little Women – Kayleigh Dray, Digital Editor 

Gillian Anderson’s 1994 adaptation of Little Women is the cinematic equivalent of wrapping your hands around a hot mug of cocoa on a rainy day and taking a deep, delicious sip. Because everything about it – from the music, to the costumes, to the cinematography – is gorgeous.

As a teen, I lapped up all those sisterly squabbles and romantic trysts. And I was so utterly captivated by Winona Ryder’s Jo that I began to – subconsciously or consciously – channel her in everything I did. I stomped around in lace-up boots, wore inappropriate hats, taught myself to whistle, and prayed that my fountain pen would leak all over my fingers as I scribbled story after story after story. I cut my hair off into a haphazard pixie, almost definitely so that I could act out Jo’s tearful “my hair” scene with my own sister in the dead of night. And I decided that, like Jo, I was destined a life as a writer in the big city (although, unlike Jo, I have since been proven correct on this matter). 

But the film also taught me some valuable life lessons, too. Together, the March sisters helped me to become kinder, more empathetic. They reminded me that it’s better to give than receive, that shared experiences are far more valuable than baubles or trinkets, and that patience truly is a virtue be – no small thing, considering I was a selfish teen with a penchant for slamming doors and screaming “it’s not fair!” whenever my own Marmee initiated a curfew.

Essentially, I loved Little Women then, I love it still, and I make a point of watching it every single Christmas. Because, even now, it serves as an important reminder that it always better to be “happy, beloved, contented, than queens on thrones, without self-respect and peace”.

Booksmart – Hollie Richardson, writer 

Molly and Amy might be over a decade younger than me, but they are my new heroes. I texted my teenage sister immediately after watching Booksmart, telling her she HAS to go watch it (which probably means she’ll avoid it like everything else I recommend to her).

Along with being one of the funniest films I have seen in years, led by female directors, writers and actors, it also acknowledges and celebrates every kind of kid in school today - a far cry from the American high school tropes I grew up with. Don’t get me wrong, you’ll hear me reciting Mean Girls and Clueless lines until the day I die, but Booksmart is refreshingly fetch. 

Easy A – Regan Okey, Social Media Editor

I think I must have watched and re-watched Easy A on repeat for a week, without stopping.

I don’t know what exactly it is about Emma Stone’s Olive that I found myself relating to so much (it was probably because she was just so incredibly sarcastic), but I really respected and admired her, and I still do. Olive is fierce, and a little bit silly and I think everyone should watch Easy A once, or three times in their life.

A Cinderella Story – Lucy Robson, SEO executive

This silly and brilliant millennial retelling of Cinderella was entirely relatable for a generation of teenagers, whose most meaningful connections with other humans were all forged via secret, late night chats online. Hilary Duff’s Sam (Cinderella) is no different, in a chat room-only relationship with a mystery boy named ‘Nomad’, where they bond over their shared teenage angst, using profundities such as “I can be surrounded by a sea of people and still feel all alone.”

Luckily, rather than ‘Nomad’ turning out to be an unappealing weirdo, he is of course Chad Michael Murray, and the most popular boy in school. What are the chances then, that when they first meet at the dance, he fails to recognise her as his classmate Sam who he see’s every day at school, despite an extremely flimsy disguise, to say the least. Queue the rest of the fairytale playing out, but also in true millennial form Prince Charming is struggling to commit, which is met by the timeless quote from Sam: “Waiting for you is like waiting for rain in this drought! Useless and disappointing!” on that note, I’m going straight home to watch it for the millionth time. 

To All The Boys I’ve Loved Before – Hannah-Rose Yee, writer 

I’ve watched so many teen movies that they’ve all started to blend into each other, but it wasn’t until I saw Netflix’s To All The Boys I’ve Loved Before last year that I realised that I had never seen a teen movie that featured teens who looked like me. 

I think that’s why I had such a powerful response to watching that movie for the first time last year at the very un-teenage age of 27. I streamed it five times the first weekend it premiered on Netflix alone. And then I downloaded it onto my phone and watched it a further [redacted] times.

Even now, a year later, I think about this movie a lot. It’s certainly not limited only to the fact that it features an Asian woman in the lead role, and that it positions her as being worthy of love and attention. It’s also to do with the clever writing, the saturated cinematography and that gorgeous fever dream of a high school hunk Peter Kavinsky.

Ah, Peter Kavinsky. Peter Kavinsky! Peter Kavinsky. The best high school movies ought to have a shiny, breathless pin-up if they possibly can. And they don’t come more shiny or breathless than Peter Kavinsky. He’s one of the greats, like Freddie Prinze Jr in She’s All That, or Heath Ledger in 10 Things I Hate About You, 20% good boy energy, 80% lopsided smile that makes you weak at the knees. I love you, Peter Kavinsky!  

Images: Rex Features