by Emily Maesar, Staff Writer

“It is a truth universally acknowledged, that a teenage girl in possession of a good fortune, must be in want of the mall.” Oh, wait. Sorry, wrong Austen! 

I jest, but this month we’re taking a look at teen films that are based on classic literature. While 1995, in particular, saw a large influx of adaptations of Austen’s work (a lot of which live in the beloved canon), there’s none so remotely suited to my work here as Amy Heckerling’s modern, teenage adaptation of Emma: Clueless. And while Audrey Hepburn shines in My Fair Lady, there’s no doubt that most people my age know the very basic plotline of George Bernard Shaw’s famous stage play Pygmalion because of 1999’s She’s All That. 

Now, I did toy with adding Shakespearian adaptations into this particular piece, or even doing a whole column about just those films, but I ultimately decided against it. I do think those flicks and their place in the teenage film canon are worth examining, but they aren’t quite as… present as Clueless and She’s All That. Both of which are currently being courted for remakes with one (Clueless) being announced, while the other (She’s All That) already making it to production, with TikTok star Addison Rae as the lead. 

And that’s something I find fascinating about the staying power of both of these films. They are, at their core, stories about transformation. Sometimes that transformation is physical, but it’s also usually a “makeover of the soul,” as Cher would say. That teenagers (and former teenagers) have found those stories interesting since at least 1816 reminds us that the want to change is a universal experience, especially for those people in an age range filled with self discovery. 

So, let’s get into the movies!

Clueless is the story of Cher Horowitz (Alicia Silverstone), a teenage girl who lives in Beverly Hills with her rich father. She’s a bit oblivious, but ultimately sweet. The film is a year in her high school life as she navigates new friends, messy romance, and becoming a better person than she was at the beginning of the story. It’s a long journey that involves matchmaking, makeovers, and realizing she’s in love with her ex-step-brother, Josh (Paul Rudd). 

Written and directed by Amy Heckerling, whose first feature was the acclaimed 80s teen film Fast Times at Ridgemont High, Clueless was actually stuck in pre-production hell for years. Originally, Heckerling imagined it as a pilot (which is fun to think about since they did actually make a TV series based on the film that ran for three seasons). Once she decided on it being a film, though, it was optioned by Fox where the film went into turnaround. 

Eventually Scott Rudin (who was publicly outed as being extremely abusive) read the script and championed it. Paramount Pictures eventually won a bidding war to make the film, and it’s fair to say that Rudin’s involvement is what made it possible at all. Which is certainly something we all have to contend with, given how involved in many films Rudin has been–including films we’ve already talked about, or will talk about later this year. 

But he saw something in Clueless, and was able to bring into our lives probably one of the most influential teen films of all time. I talked in my first column in this series about how influential Buffy the Vampire Slayer was on modern, but specifically teen, vocabulary. But the series for Buffy, that allowed that vocabulary and style of speech to make it into the mainstream, was only possible because of Heckerling’s work on Clueless. Because Cher and all her friends were monstrously successful, Gail Berman thought it would be worth it to approach Whedon about making the series. 

And then, of course, there’s the fashion! ModernGurlz, a fashion YouTube channel that I love, even did an interview with costume designer Mona May about all of her work–including Clueless. That interview is full of really interesting insights into May’s choices for the costuming in the film, but in particular the yellow plaid suit that is forever burned into popular culture–even more than twenty-five years later. From full recreations in the “Fancy” music video, to high fashion pulling aspects from it for their collections, Cher’s first day of school outfit is iconic. Not to mention her simply dropping Alaia’s name, while being held at gunpoint in the Valley, skyrocketed the general public’s knowledge of the designer in question. There’s no doubt that this film simply did something for all of us, on an aesthetic level. 

So. While it’s technically a loose adaptation of Jane Austen’s Emma, most of the main characters and bigger plot points are expertly adapted for modern, 90s rich teenagerdom by Heckerling. The spirit of Austen’s original text is present and I, on just a personal level, think it’s probably the most successful adaptation of its type, in terms of where it draws its line in story fidelity and genre. 

Like, something that I think resonates with people about Clueless, and specifically about Cher, is how truly carefree she gets to be. This is, of course, because of her wealth, but she gets to play at being an adult because she has the freedom of money (and whiteness, of course, though race is not a topic of conversation in either this or She’s All That). 

I also think that Alicia Silverstone actually being a teenager (she was 19 when the flick came out in 1995) really gives the film a feeling of authenticity. Not to mention that it always tickles me that there are at least two moments where Silverstone mispronounces something (with confidence, of course) and they weren’t actually scripted as funny moments. Particularly, her saying “Spartacus” really sticks in my head as one of the funniest things in the world - and Heckerling was smart to not correct her because it’s just so Cher. It’s the little things, the “should we leave a note” things, that are both hysterical and so utterly charming. 

Now, on the less charming side of things is the cultural artifact of She’s All That. So, let’s talk about it and it’s legacy as a shockingly influential film… but also as a very mean one. Honestly, in revisiting the flick for this piece I was so surprised that it’s almost too mean to really enjoy. At least for me. 

An adaptation of both George Bernard Shaw’s Pygmalion and George Cukor’s My Fair Lady, She’s All That is the story of popular student body president Zackary Siler (Freddy Prince, Jr.) whose girlfriend breaks up with him when they return for their senior year from spring break. Heartbroken and angry, he makes a bet with his friends that he can turn any girl into his prom queen. Dean (Paul Walker) picks Laney Boggs (Rachael Leigh Cook), the resident weirdo artist girl, as the object of Zack’s prom queen project. There are complications, like the fact that Laney thinks Zack is a loser and the classic pitfall of her finding out about the bet - but eventually they both realize that they really do like each other and start dating after everything with prom shakes out.

What’s interesting about She’s All That, at least to me, is the comparisons you can make of its plot with another of the film’s 1999 contemporaries: 10 Things I Hate About You. That film is one of the aforementioned Shakespeare adaptations (based on The Taming of the Shrew) and it has a similar story of a guy trying to take out the weirdo, angry girl because someone else is forcing his hand (in 10 Things it’s because Heath Ledger’s character is getting paid rather than for a bet). But what I think 10 Things does significantly better than She’s All That is that it really makes you understand why those characters actually fall for each other. All the dots are connected in a way I just don’t think they are in She’s All That, which I think is a big issue with the writing. 

Which is how I’m going to transition into talking about the writing of She’s All That. Because, dear reader, did you know that M. Night Shyamalan most likely did an uncredited polishing of this film? No… wait. He actually said he just fully ghost-wrote the damn thing. 

After he said that, in 2013, the former head of development at Miramax, Jack Lechner, said both Shyamalan and Fleming did substantial writing on the story. According to Lechner, Fleming wrote the initial script that Miramax bought and Shyamalan did an uncredited rewrite. Lechner also said that content from both versions made it into the final cut of the film. With all that being said, Fleming is the only person credited and he’s also written the gender flipped remake coming to Netflix, directed by Mean Girls director Mark Waters, titled He’s All That.

And of the cultural legacy? Among other things, we did get the teen film parody Not Another Teen Movie in 2001. It borrows from a lot of films, but takes the majority of its plot beats from She’s All That. It also happens to be Chris Evans’s feature debut. So, I’m grateful for that, if nothing else. 

What’s fascinating to me, overall, is that I think it’s pretty clear that neither of these films particularly represent who teenagers were in the 1990s. I think they both fall into two distinct categories: who Heckerling hoped teenagers were in Clueless and who Fleming (and/or Shyamalan) thought teenagers were in She’s All That. 

I’m inclined to hope that teenagers are more on the Heckerling side of the equation, rather than the Fleming side–but I know the truth is probably somewhere down the middle. Even today. Teenagers can be horribly mean (there’s a reason Clea DuVall’s character still feels true), but I also think there’s a wealth of kindness and empathy pouring out of teenagers today. Even if it takes people a while to get off their own planet, like Cher does. 

I’m hoping He’s All That is a bit kinder than its 1999 counterpart and that the Clueless remake (should it actually happen) remains as empathetic as the 1995 film was. Because these two films are truly cultural artifacts of teenagerdom and its perception in the 1990s, and their impact into the modern era is pretty clear cut. I don’t think there’s a way to extricate either film from who we are as a culture, and I don’t know that I’d ever actually want to, given how much they’ve changed the landscape. 

I just want modern teenagers, and the media about them, to have the style and care of Cher Horowitz, and the truly iconic moments of Laney Boggs, walking down the stairs to “Kiss Me” by Sixpence None the Richer.