When it comes to adaptations of classic media, it's hard to find one that's both more bonkers, and more honest to the source material, than Clueless. Loosely based on Emma, the Jane Austen novel about a young noble girl who spends her days playing matchmaker, the film transplants the action from Regency-era England into late 1990s Beverly Hills, and yet somehow manages to keep the spirit and substance of the original story. That's not to say it's a straight adaptation in a new setting, though (so it bears little resemblance to the Joss Whedon Much Ado About Nothing in that regard) as the film is smart enough to make the changes needed to update and modernize the film to make it work for the generation that would have been watching it at the time.
Clueless is a film that's easy to fall into, a bit of a silly trifle where you hang out with a privileged, but sweet, girl as she goes about her life during a semester of high school. She makes new friends, tries to help people, and comes at everything from her sweetly oblivious bubble. It would be easy to hate this girl if she were presented in any other context, but the movie, written and directed by Amy Heckling (who had previously directly Fast Times at Ridgemont High, National Lampoon's European Vacation, and the first two Look Who's Talking films) knows how to present her in such a way that the audience loves instead loathes her. It's a smart, tight balancing act that could have gone very poorly very quickly.
Cher Horowitz (Alicia Silverstone) is a rich girl who has everything. Her father, Mel (Dan Hedaya), is a powerful lawyer who can afford to give her everything she wants. She the most popular girl in school, beloved and wanted by everyone. She and her best friend, Dionne (Stacey Dash), essentially run the school and there's almost nothing they can't do. Hell, even when she gets bad grades on her report card, Cher is able to argue her grade up, taking a C-plus average up to an A-minus. This, to say the least, impresses her lawyer father to no end.
In the process of helping her own grades, though, she gets the bug for helping others. When she pairs up two teachers together (to make them both happier and, in the process, improve her own grades), she decides she wants a further project to work on. That's when she meets new student, Tai (Brittany Murphy) a girl desperately in need of a makeover. She and Dionne remake Tai's look, help her with her life, and generally try to make her into a clone of themselves. But will Tai's popularity at the school eventually eclipse Cher's own? And as she's helping everyone else, when will she find time to really help herself?
As a loose remake of Emma, there are a number of elements that are carbon-copied over in one respect or another. Tai is a stand in for Harriet Smith, a young, unsophisticated women that Emma takes under her wing. Cher meddles in Tai's love life (in another parallel), shooing her away from a match that actually could be good for her (in the long run) towards a man who has no interest in the young woman. Cher finds a love connection for two teachers at school, much as Emma found a suitable match for her friend, and former governess. The elements line up enough to make the inspiration fairly obvious.
And then there's the love story for Cher. As in the novel, this version of the Emma character tries, and fails, to find love all before realizing that her own love connection was right in front of her: her (former) step-brother, Josh (Paul Rudd). The chemistry between Josh and Cher is palpable, with them going from antagonizing siblings to falling for each over the course of the film. With that said, one of the flaws of the film is the age difference between Josh and Cher. He's in college, and (while never specified) likely at least a senior, while Cher is a high schooler working on her learner's permit (so no older than 16). It's a stark enough age difference that the love story between them does feel just a little sketchy. In fairness, in the original novel Emma was 20 and Mr. Knightly, her own live interest, was 36, so the age difference was even larger there. But it still seems icky now, when you think about it. Making Josh slightly younger, or declaring him a freshman in college, could have helped this a lot.
Of course, what sell so much of this film is the lead performance from Silverstone. While not her break out role (she'd starred as the crazy stalker girl in The Crush in 1993, and had appeared in a trio of Aerosmith music videos as well), it was Clueless that really put her on the map. He performance here, blending ditziness, obliviousness, sweetness, and caring, is the kind of tightrope act that most actresses (and actors) couldn't pull off. Hell, just go and watch the loose spin-off TV show, also called Clueless, starring Rachel Blanchard in the Cher role, so see just how well Silverstone handled this. Cher could come across as too self-invested, too oblivious, too uncaring, but Silverstone manages to find a core to the character that really works. She's a likable protagonist despite her landed wealth and nobility status in life and school.
And while I do pick at the age difference between the leads, there is no denying that Paul Rudd was a charismatic foil for Silverstone. Their chemistry is palpable, yes, but the two also have solid comedic repartee as well. Their back and forth bickering is fun to watch, and there's a lightness, and easiness to it that feels lived in. Rudd has, of course, continued on since then playing likable, easy going leads in a lot of films, and Clueless . In fact, Clueless was Rudd's first on screen role (followed closely by the awful Halloween: Curse of Michael Myers) and it's clear here why the actor has had such staying power in Hollywood.
But, even more than the stars, what is most deserving of praise is Heckerling's script. The writer has been praised, and rightly so, for delivering a set of characters with their own lingo, their own way of acting, that would go on to influence the generation (and future writers as well). As soon as this film came out, "as if!" became a regular statement for months (and years, even). There are any number of catchy phrases and words that the characters say that, now nearly 30 years later, as so ingrained in normal speech that they don't even sound odd or funny anymore.
The film is still funny, mind you. The script is littered with a ton of jokes, many of them at the expense of Cher and her friends because of their own obliviousness and the bubble they live in. It's not mean spirited humor, which is why it works, it just helps to deflate them a little and say, "hey, they may have all this money but they really are, well, clueless." And despite having seen this film a number of times over the years, I do still find myself laughing regularly during the film. It has a way with its turn of phrases, with the reactions from the actors, with the comedic pacing, that keeps it funny even all these years later.
If there is any other flaw with the film it's that it isn't quite as timeless as it once was. There are regular references to actors that either seem simply dated -- Cindy Crawford, the Baldwins, Luke Perry -- or are outright cringey -- Cher proudly declaring herself a fan of Mel Gibson, for example. All of the tech in the film is dated too, from large CRT monitors to chunky, old school flip-phones. Hell, at the start of the film, Cher uses a computer program to pick out her clothes and it's supposed to highlight how rich and out of touch she is; now, though, I expect there's 300 different apps like that in the Play store right now. Of course, the biggest thing that stuck out to me is when, in a scene, Cher loses her phone and has to call her step-bro for help. She knows his number, from memory. Who still remembers numbers anymore?
These are, of course, minor quibbles for a film that otherwise still holds up really well. The film continues to have it's fans, being held up as one of the great comedies of the 1990s, and it's true. Whatever else may have come out after it -- the less impressive TV show, a series of novels no one cared about, a reboot TV show that still has yet to get off the ground -- that doesn't take away from the greatness of this film. It's a light, bubbly, enjoyable remake of the Emma story, and whether you like it because of it's literary roots or just because it's a great comedy, the film is a fun comedy to watch.