Silverstone's hobby is improving the lives of others. She matches whiny-voiced Wallace Shawn with fellow teacher Twink Caplan. She transforms new girl Brittany Murphy into a socialite, but fails in setting her up with Jeremy Sisto. After all, Murphy has more in common with stoner Breckin Meyer. Meanwhile, Silverstone fails to observe the obvious, that she belongs with hunky Paul Rudd.
How others will see it. A summer box office smash, Clueless set Hollywood abuzz about the career prospects of Alicia Silverstone, the "It" girl of 1995. Then she gained a few pounds (gasp!) and was cast in a bad Batman movie, and the star parade moved on to Sarah Polley or whomever.
There were undoubtedly some folks who were not surprised that a nice rich teenage girl like Silverstone could make the great stretch of playing a nice rich teenage girl. Some folks even realized that it was writer / director Amy Heckerling that was responsible for the success of Clueless, namely those on the boards of the Writers Guild of America, and the New York Film Critics Circle, who nominated her for Best Screenplay.
Today at imdb.com, Clueless has a high 144K user ratings, which demonstrates that the film is iconic if by no means universally well regarded. In fact, men between the ages of 30 and 45 grade it a mere 6.4 out of 10, though women over 45, my favorite demographic, give it a more respectable 7.3. It is probably no surprise that American viewers grade it more highly than do those outside of the U.S., with grades of 7.0 versus 6.6.
User comments note that the movie is based on Jane Austen's "Emma", whose story is conveniently in the public domain, though I missed the chapter where Emma's would-be boyfriend turns out to be gay. The user comments are generally glowing, with "Joyous and sparkling" as a typical headline.
How I felt about it. I first saw Clueless about twenty years ago. I graded it highly, and published a positive review. Someone who had been reading my reviews, and actually believed in my grades, was not happy with my judgment on Clueless. He couldn't understand why I graded Clueless, a film tailored at teenage girls, much higher The Conversation, the Coppola film sandwiched between the first two Godfather movies.
Well, those two movies are great. They are even better than Clueless. But Woody Allen's success with Annie Hall (1977) and Manhattan (1979) doesn't make Interiors (1978) any more watchable. In other words, you have to judge a film on its own merits, and not because a certain director made them during his or her "good" period. Hitchcock, for example, scattered great movies over a long period of time along with movies that are clearly not so good, not that I've actually seen Jamaica Inn (1939).
What I am saying is that Clueless can be a really good movie, even though it was written and directed by a woman before such things were heralded, and even though the movie is targeted to young women. They deserve good movies too, you know. The Twilight series didn't cut it.
And it isn't that Heckerling never made any other good movies. Any American teenager in 1982 could tell you that Fast Times at Ridgemont High was good. It even made a star out of Sean Penn, not to mention Phoebe Cates, Jennifer Jason Leigh, and Judge Reinhold. Look Who's Talking was also really good for a comedy, even if it was targeted to women in their 30s. And it did have one of the funniest gags I have ever seen, George Segal exploding. You had to be there.
The big rap on Clueless, besides the fact that Stacey Dash was ten years too old to be in high school, is that the movie gradually morphs from an LOL (I know you hate that abbreviation, but it is such a time-saver) satire on rich teen culture into a "who am I really" self-evaluation, that predictably ends up in the hottest girl hooking up with the hottest guy. As if nobody could see that coming. Marlo Thomas, bless her heart, would undoubtedly opine that Alicia Silverstone doesn't have to commit to anyone. She can go to college without a perfect ten special other, just like everybody else.
Which only proves that Clueless isn't as great as Casablanca, but it remains one heckuva teen comedy, with a bang-up screenplay and a few worthy moments of introspection.