This is Cher (Alicia Silverstone), a teenage girl in Beverly Hills who like her best friend Dionne (Stacey Dash) was named after a famous singer who now does infomercials. She attends a high school there, and considers herself very popular, no wonder when she spends so much time on her clothes and makeup and ensuring everyone around her is in positive mood, even her grumpy litigator father (Dan Hedaya) who strikes terror into the hearts of most people. Her mother passed away when she was very young, and dad remarried, then divorced, though he is still in contact with his ex-stepson Josh (Paul Rudd) who hopes to follow in his footsteps into the law business, but is currently in college. As for Cher, there's nothing she likes more than a project...
Not necessarily a school project, more a personal one, and not necessarily her own person either as Cher was based by director Amy Heckerling on a literary heroine, Jane Austen's do-gooder Emma. As an example of how Austen was revived in popularity in the nineteen-nineties, that wasn't the only sign Clueless was set to become a time capsule drawn from a position slap bang in the middle of the decade, as some of its humour was so time specific you'd imagine the gags about how often the characters use their mobile phones would be lost on viewers a short time later as the technology became ubiquitous. Then there were the fashions so set in 1995 that you imagine Cher and company might as well have been kitted out in corsets and bustles.
Naturally, if this were all about capturing the spirit of the age both in dialogue and appearance, Clueless would have become a nostalgia piece and little else, but as Heckerling had achieved with her eighties snapshot Fast Times at Ridgemont High there was more to this than the pretty faces, as that positive attitude of its heroine was put under the microscope and found wanting. Not that Cher was a bad person, she was simply rather blinkered by her privileged lifestyle and needed a gentle nudge in the right direction to get the benefits of a rounded personality: friends, romantic partner, valuable contribution to society, and so on, though not necessarily in that order. She already thinks she is making a crucial contribution by cheering others up, mostly by matchmaking.
She sets up two of her teachers (Wallace Shawn and Twink Caplan, who was a producer here) for a relationship, though she does so for selfish reasons as she works out if her teachers are happy, they will award her better grades, and she's right about that, indicating good deeds are as much about the satisfaction it gives the do-gooder as the ones they benefit. Yet that is no reason not to try and help, the film tells us, simply be aware of the bigger picture and you will be far more benelovent in your actions and their ultimate effect. If that sounds a bit heavy for a frothy teen comedy, there are scenes in the last act where Cher is suffering a crisis that's entirely her own fault, because when a new girl arrives at school, Tai (Brittany Murphy), all she can see is a problem to be solved.
Tai would have probably got on very well with skater boi Travis (Breckin Meyer), her most obvious boyfriend material and not because they both share an interest in getting high, but when Cher takes her under her wing she mistakes her social status as aspiring when the girl would be content where she was, meaning the inevitable "I've created a monster!" realisation for Cher by and by. Yet even if there are harsh words shared, Heckerling liked her characters too much to give them problems that were insurmountable - even her lead's nemesis, Amber (Elisa Donovan) is pretty harmless when you get down to it - therefore the overall effect was sweet rather than the bitchiness it could have lapsed into in other hands. If a good many of the jokes were very tied to a time and place, the director did an effective enough job of not populating her film with crushing caricatures which would have sabotaged both the humour and how cute the whole thing was, and Clueless remains winning even after its heyday is long gone. The nostalgia factor is always to be reckoned with. Music by David Kitay.