Now, I'm sympathetic to this message, because high school, let's face it, was not a pleasant experience. But it's not all bad either, and unless you grew up to become a rich Hollywood producer, we might find that our adult lives aren't all that much better than high school. So there's always room for a movie that takes a different tack, and what Clueless does is to focus on how few real problems a high school student has to face -- particularly if, like Alicia Silverstone's Cher, that student happens to be attractive, rich, and clever enough to argue her way out of any situation. (It's implied that Cher will grow up to be a lawyer like her father.) Cher's problem is that she doesn't have enough problems; like Jane Austen's Emma, she has lived "with very little to distress or vex her," to the point that she can't accept that things won't always turn out exactly as she plans them.
Most teen movies and shows are about characters who are denied the things which they feel they're entitled to, and whose fulfilment comes in getting those things: Molly Ringwald gets her big date, Ferris Bueller bucks authority; the Freaks and Geeks grow up to be Judd Apatow and Paul Feig. Clueless is about a character who learns that she's not always entitled to have her own way, that in fact sometimes good things happen when she's not always scheming to get her own way; that's one of the things that makes it different from other teen movies, and so refreshing.
Also, I'm hardly the first to mention that Clueless is the best movie ever made from a Jane Austen novel. Here is a point-by-point comparison of Clueless with its source, Austen's Emma. There are other, smaller points of similarity; Emma's boredom with village life is parallelled in Cher's boredom with high school boys.
Clueless has the distinction of featuring two actors, of opposite sex, who went on to voice the same cartoon character. Brittany Murphy (Tai) became the voice of Joseph Gribble on King of the Hill (she still does the voice of Luanne), and Breckin Meyer (Travis, Tai's love interest) took over the voice of Joseph after the character went through puberty.
Finally, the best thing about Clueless is the dialogue, a half-literate half-slangy jargon that's sort of the Beverly Hills High School equivalent of Damon Runyon. Some great examples:
CHER: So like, right now for example. The Haiti-ans need to come to America. But some people are all, "What about the strain on our resources?" Well it's like when I had this garden party for my father's birthday, right? I put R.S.V.P. 'cause it was a sit-down dinner. But some people came that like did not R.S.V.P. I was like totally buggin'. I had to haul ass to the kitchen, redistribute the food, and squish in extra place settings. But by the end of the day it was, like, the more the merrier. And so if the government could just get to the kitchen, rearrange some things, we could certainly party with the Haiti-ans. And in conclusion may I please remind you it does not say R.S.V.P. on the Statue of Liberty. Thank you very much.
MURRAY: Street slang is an increasingly valid form of expression. Most of the feminine pronouns do have mocking, but not necessarily misogynistic undertones.
MEL: Anything happens to my daughter, I got a .45 and a shovel. I doubt anyone would miss you.