privileged high-school sophomore who also happens to be clever and kind. And in Cher's world, the ultimate kindness is to lead someone into love. She sets her teacher up on a date when his unhappiness gets in the way of her receiving a good grade; and when an awkward new girl comes to their school, Cher and her best friend Dionne (Stacey Dash) make it their mission to give this clueless girl a makeover.
Tai, the new girl in school, is played to wide-eyed perfection by Brittany Murphy. It's sad to see her now in this early role, struggling to find her way with the popular kids. She's so good, and so believable—it's another reminder of the charm and talent that died with her.
Tai has a crush on rich-kid Elton (Jeremy Sisto, whose name Tai pronounces "EL'in"), so Cher and Dionne scheme to get the two together. Tai gamely goes along with the plan, but Elton is nursing a crush on clueless Cher.
Meanwhile, Cher's ex-stepbrother, sigh-worthy Josh (Paul Rudd), is home from college. He and his environmental concerns are a source of annoyance to Cher at first, but she slowly comes to realize just how deep and interesting he is, sort of like Cher herself.
There's a very funny scene in which Tai "almost dies" at the mall, and all sorts of other brilliant touches of 90s pop culture standing in for Emma's 19th-century setting.
That's the genius of Clueless, which Heckerling both wrote and directed. It's not just an arbitrary updating of a classic in an attempt to be clever (like often happens with modern settings of, for example, Shakespeare's MacBeth or A Midsummer Night's Dream). Instead, Clueless is clued in to exactly what makes Emma work.
Emma is set in a time when class and social standing were paramount; these ideas dominated everything from guest lists to marriage prospects. Combine that emphasis on social standing with the fact that privileged young ladies had all the time in the world to call on one another and very little else to think about, and you have the makings of incessant gossip and interpersonal meddling that is truly timeless. As Heckerling shrewdly perceived, the only modern setting that matches that 19th-century backdrop is high school. That was true in the 90s and remains true today, giving her film a surprising staying power. Heckerling and her impeccable cast show viewers the seamless connection between Austen's world and Cher's, meanwhile creating a movie that is tons of fun even for viewers who aren't the least bit clued in to Emma.
Clueless stands as a 1990s period piece with truths that transcend its setting. The language, clothes, and accessories immediately return viewers to the middle of the decade. Not only that, it's a great cast and a funny story. Altogether satisfying.