By their very nature, teen films tend to get dated very quickly.  Fashions, music, and cultural references — all of these serve to make a film popular when it’s first released and occasionally laughable just a few years later.  Take 1995’s Clueless for instance.  Watching it now, it’s impossible not to get a little snarky when Cher Horowitz (Alicia Silverstone) refers to a hot guy as being a “Baldwin.”  When heard today, it’s hard not to wonder if Cher is thinking of beefy rageaholic Alec or ultra-religious realty TV mainstay Stephen.  (Personally, I prefer to think that she was thinking of Adam Baldwin.)

Clueless is one of those films that I always remember watching on TV and loving when I was little but, whenever I watch it now, I always find myself feeling slightly disappointed in it.  It’s never quite as good as I remember and, with each viewing, I’m just a little bit more aware that, while both were very well-cast in their respect roles, Alicia Silverstone and Stacey Dash weren’t exactly the most versatile actresses of their generation.  There’s a reason why Dash is now a political commentator and Silverstone is best known for that video of her spitting food into her baby’s mouth.  As well, watching the film now, it’s hard not to think about how the talented Brittany Murphy would tragically pass away 14 years after its initial release.

And yet, I can’t help it.  I still enjoy Clueless.  I could spend hours nitpicking it apart and pointing out what parts of it don’t quite work as well as they should but ultimately, Clueless is a fun movie that features and celebrates three strong female characters, which is more than you can say for most teen films.

Directed and written by Amy Heckerling (who earlier directed the classic Fast Times At Ridgemont High), Clueless is based (quite directly) on Jane Austen’s Emma.  In this version, Emma is Cher, the spoiled 16 year-old daughter of a lawyer (played, very well, by Dan Hedaya), who lives in Beverly Hills and who is happy being superficial, vain, and popular.  In fact, the only person who ever criticizes Cher is her stepbrother, Josh (Paul Rudd), who is studying to be an environmental lawyer and is visiting during a break from college.

When Cher plays matchmaker and deftly manages to pair up two of her teachers (played by Wallace Shawn and Twink Caplan), she realizes that she enjoys helping people.  (Though, it must be said, the only reason she helped her two teachers wass because they were both taking out the misery of being single on her…)  So, Cher and her best friend Dionne (Stacey Dash) decide to help another student, new girl Tai (Brittany Murphy), become popular.  After giving Tai a makeover, forbidding her to date skater Travis (Breckin Meyer, who is adorable), and trying to set Tai up with rich snob Elton (Jeremy Sisto), Cher is shocked to discover that Tai has become so popular that she is now challenging Cher’s social status.  Even worse, Tai decides that she has a crush on Josh right around the same time that Cher realizes the same thing.

Plus, Cher still has to pass her driving test…

As I said before, Clueless is hardly a perfect film but it is a very likable movie.  Director Amy Heckerling creates such a vivid and colorful alternate teenage universe and the script is full of so many quotable lines that you can forgive the fact that the story sometimes runs the risk of getting almost as superficial of Cher.  It may never be quite as good as I remembered it being but Clueless is still an entertaining and fun movie.