I’m going to start off by saying, “How have I not seen this film before?!”

I didn’t really know what Clueless was about. Obviously I had heard about it and knew that it had become a classic teen film, but for some reason I had never seen it. Then, scrolling through Amazon Prime, I saw it and thought I may as well watch it.

Well, all I can say is what a great decision that was!

Clueless is a genuinely funny teen comedy, with engaging characters, a good story, and some touching moments that make this film stand out from the countless other films in this genre.

Dionne Cher and Tai
Cher, Dionne, Tai

The plot is loosely based on the Jane Austen book Emma, which perhaps explains why the story is so good! Although a modern-day (well…90s) version of Emma may seem unnecessary and die-hard Austen fans may shudder at the thought of it, I think Clueless has perfectly captured the feel of the story and the central character and is worthy of merit in its own right.

Directed by Amy Heckerling, Clueless is a real feel-good film without ever straying into the territory of cliché and cringiness. Packed with genuinely laugh-out-loud moments, brilliant quotes, romance, and, of course, the irresistible main character of Cher Horowitz, Clueless has appeared out of nowhere to become one of my favourite films!

Plot summary

Clueless is centred around Cher Horowitz (Alicia Silverstone), a popular and stylish student who lives in a Beverly Hills mansion with her widowed father (Dan Hedaya). From the beginning Cher appears to be your classic “Valley Girl” teen and, along with best friend Dionne (Stacey Dash), she is one of the “coolest” and most popular students at school.

Cher in class
Cher Horowitz- matchmaker extraordinaire

Also in the picture is Josh (Paul Rudd), Cher’s sort of ex-step brother who is staying at their house. They are very different- college student Josh is concerned about the world and its issues, while Cher is very self-absorbed and more concerned about shopping, popular culture, and how she looks. They constantly bicker and disagree, but it’s all good-natured and their relationship slowly develops throughout the film…

After she gets a lower grade than she wanted in class, Cher thinks the way of improving it is not by working harder, but instead by playing matchmaker between two teachers at her school- Mr Hall (Wallace Shawn) and Miss Geist (Twink Caplan). This works, and the two teachers in their newfound happiness from their romance are more inclined to give out good grades.

After the success of this, Cher looks for more good deeds to do. Enter Tai Frasier (Brittany Murphy), a new girl who Cher and Dionne plan to make fashionable and cool.

Tai Frasier
Unsuspecting Tai

Cher and Dionne take Tai on as their pet project, giving her a makeover and turning her into one of the “popular” girls. They try to make her lose interest in Travis Birkenstock (Breckin Meyer), a skate boarding student (and stoner) who they don’t consider a good match, and try to set her up with the incredibly popular Elton (Jeremy Sisto).

However, unknown to Cher, Elton in fact fancies her and tries kiss her, which Cher completely turns down.

Cher in a Calvin Klein "dress" with Christian
Calvin Klein says this is a dress

Cher then pursues a seemingly perfect student called Christian (Justin Walker), perfect for her except the fact he is gay, as Dionne’s boyfriend Murray (Donald Faison) points out.

Towards the end of the film Tai and Cher’s friendship becomes strained and Cher is forced to look at herself and her relationships. She realises that she actually has feelings for Josh, and aims to do more charitable and humanitarian deeds like leading the Pismo Beach relief work.

As expected, Cher and Josh end up together and they all live happily ever after!

Josh and Cher sitting
Josh and Cher…kind of weird but kind of sweet

Who doesn’t love Cher?

Cher Horowitz is the best thing about Clueless. Played fantastically by Alicia Silverstone, Cher is such a magnetic character and she steals every scene she’s in.

If I could dress and look half as good as Cher then I would definitely feel like I’m winning at life.

Throughout the film we regularly hear Cher’s thoughts through voiceovers, which helps us see things from her perspective and makes us feel more sympathetic towards her. Her voiceovers are incredibly memorable and highlight the many quirks of how Cher thinks!

Cher tries to act grown up, but is in fact quite naïve. However, perhaps surprisingly, she is intelligent in her own way!

She may not know where Bosnia or Kuwait are, but she knows about pop culture, has a lot of sense and her arguments in class about Haitians in America and violence on TV are actually quite convincing. Even if she can’t actually pronounce Haitians correctly…(which was apparently a genuine mistake by Silverstone).

Cher in car after failing driving test
“You can’t be the absolute and final word on drivers licences?”

It could have been easy for Cher to be a selfish, spoilt, unlikeable, bitchy character, but she was quite the opposite. Yes she was self-absorbed and more concerned about shopping and fashion than educating herself about the issues of the day, but it was obvious she meant well with everything she did.

She looks after her dad (trying to make him healthier), she’s a great and supportive friend, she’s always positive and doing things for others, and she likes to see people happy.

Cher is definitely not perfect, notably when she doesn’t understand why it matters whether her housekeeper comes from El Salvador or Mexico. Also, Cher and Dionne taking Tai under their wing is quite selfish as they tried to change Tai’s image to suit them, but again they meant well and they all do become genuine friends in the end.

Whatever Cher does, even if it’s questionable, it’s impossible to dislike her as she’s not deliberately being hurtful or malicious!

Throughout the film Cher is always shown to know her own mind, but she also starts to learn and grow up towards the end. Unlike some films Cher doesn’t undergo a massive U-turn and suddenly become responsible and mature; she is still recognisably the Cher from the beginning of the film, it is just she is starting to become more aware of things outside her privileged life (although clothes are probably still her main priority!)

Tai, Cher, and Dionne at school
Three friends

Here come the girls

Clueless is great for showing supportive female friendships. Cher and Dionne are close, and they welcome Tai into their circle with no problems. Admittedly their motives for being friendly weren’t entirely selfless, but they were never snide or cruel to Tai or made her feel left out.

Too often we might see teen girls judging each other and getting into petty battles trying to outdo each other. And, the biggest cliche of them all, falling out over boys.

However, Cher, Dionne, and eventually Tai, support each other and are able to have quite mature and open conversations about sex for example. Even when Tai and Cher argued, they were able to get past it and make up, which is really refreshing for a film centred on teen relationships!

He is kind of a Baldwin

It was pretty obvious that Cher would end up with Josh (especially if you know the story of Emma), even though the fact they were sort of step-siblings makes their relationship a bit questionable. I’m happy to overlook it though as I think they made a great couple!

They bickered a lot but they were evidently fond of each other. You saw this from Josh when he defended Cher after one of her dad’s team got annoyed at her when she messed up with some documents. Also when Cher came down in her infamous Calvin Klein dress you could see Josh was feeling a bit confused and overcome!

From Cher’s side it took longer to realise her feelings. It wasn’t until she was trying to understand why she didn’t like the idea of Tai and Josh together that she suddenly concluded she liked him.

Cher and Elton
Cher and Elton? Ugh..As if!

Another reason why Clueless stands out from your standard teen rom-com is that it does touch on some serious issues, notably the scene when Elton tries to come onto Cher in the car.

It had some serious undertones and raised the topic of consent. It also highlighted the fact that Cher is at heart just a vulnerable young teenager and showed Elton to be a nasty piece of work. When Josh comes along to get Cher like a knight in shining armour, then you know things will only end one way!

Favourite Clueless Quotes

There are so many amazing quotes in Clueless. Before watching the film I read about how quotable it was, and they were not wrong!

The entire film is worthy of being mentioned, but a selection of my favourite quotes are:

“Dionne and I were both named after famous singers of the past, who now do infomercials.”

Cher

“So okay, I don’t want to be a traitor to my generation and all but I don’t get how guys dress today. I mean, come on, it looks like they just fell out of bed and put on some baggy pants and take their greasy hair – ew – and cover it up with a backwards cap and like, we’re expected to swoon? I don’t think so.”

Cher

“You see how picky I am about my shoes and they only go on my feet.”

Cher (talking about boys):

“I was surfing the crimson wave.”

Cher (talking about her period):

“I don’t get it. Did my hair get flat? Did I stumble into some bad lighting? What’s wrong with me?”

Cher (after Christian walks out)

And possibly my favourite part in Clueless:

Mel: “I don’t think they need your skis.”

Cher: “Daddy, some people lost all their belongings. Don’t you think that includes athletic equipment?”

When Cher donates her belongings to the Pismo Beach relief effort
Cher and Dionne in plaid
Iconic outfits

I also loved how Clueless combined pop culture references to older and more classic novels or artists, like when Cher compared people to artworks by Monet and Botticelli.

“She’s a full-on Monet…It’s like a painting, see? From far away, it’s OK, but up close, it’s a big old mess.”

Favourite Clueless Scenes

I’m tempted to just say the whole film is my favourite scene because there are just too many iconic moments to choose from!

However one that sticks out in my mind is when Dionne is driving with Cher and Murray and accidentally ends up on the freeway.

The switching on the windscreen wipers instead of indicating, the screaming and the panic, the old lady in the car, the massive truck, there’s so much packed into just one minute!

You could feel their stress and panic and it was definitely an accurate representation of how I felt when I learnt to drive! I don’t know why this scene doesn’t seem to be talked about more as I found it one of the funniest visual scenes in the film!

I say visual scenes because there were just so many classic lines which were incredibly witty and funny. One of my favourites was after Josh and his girlfriend Heather picked up Cher, and Heather tried to sound intelligent but just ended up looking like a fool!

Heather: “It’s just like Hamlet said, “To thine own self be true.””

Cher: “Hamlet didn’t say that.”

Heather: “I think I remember Hamlet accurately.”

Cher: “Well, I remember Mel Gibson accurately, and he didn’t say that. That Polonius guy did.”

Finally…

If you haven’t already, watch Clueless! Don’t make the same mistake I did and wait 24 years. And if you have seen Clueless, it’s time to watch it again!

It is one of the wittiest and funniest films I’ve seen, with one of the best film characters ever in the shape of Cher Horowitz.

“Iconic” and “must-see” are terms thrown around a lot in the film industry, but Clueless deserves every word of praise it gets.