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This came out in 1995, though I probably didn't see it until at least a few years later. I forget when exactly I first saw it. But anyway, I suppose the second time I saw it was in 2012, which is when I'm writing my review. I should say, the movie was quite popular when it first came out, and started a number of trends, perhaps most notably in slang (or at least popularizing Valspeak outside California). Looking at the movie now, it seems kind of dated, for various reasons, but the mid-90s were kind of an interesting transitional time, I think. I mean, for example... look at the kids' cell phones. They look kind of clunky by today's standards, but if you see any movies with cell phones from the 80s, the ones in this movie are definitely a lot less clunky. (Of course, the inclusion of cell phones in the movie at all was meant to be just one more aspect of how spoiled the kids were, as mentioned in the TV Tropes link above, which is ironic in retrospect. But on the other hand... not too many years earlier, even rich kids wouldn't have had them, because they simply didn't exist. So, like I said... a transitional era.)
I also want to mention that I wasn't quite sure what category to put my review in. I was thinking comedy, then I thought, dramedy. Then I thought maybe I'd add a seriocomedy subsection to my movie section, as dramedy was a subsection of drama. Then I thought about making a whole third category for seriocomedy movies, separate from both comedy and drama. Then I thought that'd be too much work, especially so late at night, so I was just going to put my review in romantic movies. Then I changed my mind, and decided to start the seriocomedy section, after all, and I moved five movies from dramedy and one from comedy, to the new section, in addition to adding a new review for Clueless. You don't care about any of this, but I do, so there.
Oh yes, and as I was watching the end credits, I thought, "Maybe I should try to write my review with the kind of slang in the movie." But then I was all, "As if. That'd definitely be too much work." But I will say this: the girls in this movie are all total Bettys.
Anyway, it's set in Beverly Hills. The main character is a high school girl named Cher Horowitz (Alicia Silverstone, in the role that made her famous). Cher narrates her thoughts throughout the movie. Oh yeah, I also need to mention that the movie is commonly considered a loose adaptation of Jane Austen's novel "Emma," which I've never read, though I must have seen at least one movie based on it. I remember nothing of the story or characters, so I can't really comment on any similarities in this movie. Anyway, Cher's father, Mel (Dan Hedaya), is a lawyer, and a widower (Cher never really knew her mother). At some point, Mel was remarried to another woman, who had been married at least once before, and had a son named Josh (Paul Rudd). Josh's mom and Mel are now divorced, and she's moved on to yet another husband (her fourth). So anyway, Josh, who is in college, and studying to become a lawyer, is Cher's "ex-stepbrother," but still seems to have a better relationship with Mel than his own mother (and certainly better than his relationship with his new stepfather). As for his relationship with Cher, they kind of act like your typical siblings who find each other annoying, or whatever. At least most of the time.
Cher's best friend is Dionne (or "Dee", played by Stacey Dash), who's dating a guy named Murray (Donald Faison), though Dee and Murray seem to argue a lot. And there's another girl at school named Amber (Elisa Donovan), who does not get along at all with Cher and Dee. Um... the movie spends a little while just letting us get familiar with Cher and her lifestyle, before really kicking off the plot. That begins with Cher getting a report card with grades that aren't as good as she'd like. So she finagles grade bumps from almost all her teachers (which pleases her father, because it shows she has debate skills, just like a lawyer; though ironically, in her debates for one of her classes, she's not quite as good). The one holdout was Mr. Hall (Wallace Shawn). She decided the reason he refused to bend on his grade is that he was unhappy... because he was single. So she got Dee to help her trick him and another teacher, Ms. Geist, into starting a relationship. The scheme is a stunning success not just for Cher, but pretty much all the students of both teachers. That gets Cher wanting to do more "good deeds."
Her next project comes along in the form of a new student named Tai (Brittany Murphy). Cher convinces Dee to help her make Tai more popular and self-confident and whatnot. Tai forges an immediate connection with a stoner named Travis, but Cher discourages that, and tries to set Tai up with a popular guy named Elton (Jeremy Sisto), though that... doesn't go so well. Later, Cher starts dating a guy named Christian... which also doesn't go quite as she expected. And... things continue to get complicated in various ways. I don't want to spoil any more plot developments, but I will say Josh gradually becomes much more important to the plot than he seemed at first. And the movie does have a really happy ending for just about everyone.
Anyway, the movie has some great music. And it's all really funny and sweet and cool and stuff. Cher is very likable, far more so than you'd expect a spoiled rich girl to be. She pretty much... well, I mean, she is totally true to certain stereotypes, but simultaneously subverts certain stereotypes. It's a very neat balance, which is greatly helped by hearing her inner monologue, so she basically comes off as... an ordinary teenage girl (which puts me in mind of the theme song from the TV spin-off of the movie; see other stuff). Anyway, all the actors in the movie did an awesome job, especially Silverstone. I guess that's all I can think to say (I hope I'm not forgetting anything important). It was just a really fun movie.