The movie is basically set around the life of pampered rich girl Cher (played by Silvertone) who can argue anything to get what she wants, as taught to her by her lawyer father (played by Hedaya). In her high school, she is the leader of a group of girls just as vain and clueless as she is, including her best friend Dionne (played by Dash). Brittany Murphy plays Tai, a new student at the school whom Cher takes on as her charity case to make her over into one of the groups. When Tai's personality changes Cher then sees firsthand how she treats people and ultimately learns to grow up. The other big plot revolves around Cher's love life. She tries to make out with her school crush and is surprisingly rebuffed, and then falls for Rudd's character, which is a bit creepy given that he is her stepbrother.
For those who get the Whatever! edition of the DVD, the extras include the trailers, a bunch of behind-the-scenes featurettes (seven in all ranging from about three minutes to almost twenty minutes), and then a bunch of previews for other movies. So, if you like bonus material, you get a good amount here.
Overall, the movie is a classic. It is very funny and has some dramatic moments. Yes, the thought of Cher and Josh becoming a thing is a bit creepy and is probably not something that would be added to the storyline if it was made today, but it was not the focus of the movie by any means. Of course, the various actors have gone on to have wildly varied careers since Clueless with Silverstone basically having retired from acting, Rudd making blockbuster movies (and hardly aging), and Murphy having tragically passed away after her career hitting a bit of a slump. It would be nice if they make a 20th-anniversary Blu-Ray within the next couple of years and get the cast together to do a commentary track and new cast interviews. Who knows whether that will actually happen, but for now, this is a great version of the movie (there is a Blu-Ray upgrade of this set floating around out there), and it is definitely worth watching.