Clueless
★★★★
I have now watched Clueless three times within the past three years, and I will admit, the brilliance of this film has grown on me. Back on my first rewatch in 2020, I noted that I thought Clueless was way overrated. I have completely changed my outlook. I originally saw it as a nostalgic, pop culture timepiece from the '90s, which it totally is. But what I have really noticed over multiple viewings is how director/writer Amy Heckerling tells this simple story to mean different things to multiple generations. The enjoyment that teenagers will gain from this movie is a different experience than a parent, yet everyone will enjoy their experience.
There is such a fun and free flow to all the scenes. This wouldn't be nearly as effective if Alicia Silverstone wasn't perfectly cast in this film. Cher could have simply been an airhead that we laugh at, but instead, we admire her confidence and ever-present street smarts. Heckerling has written a character who is supremely privileged and spoiled, but we root for her because somehow her heart always seems to be in the right place. As an adult, it's a delight to smirk at what Cher thinks are tragedies in life.
It's interesting watching Clueless from a romantic comedy perspective because I always saw it as just a teen movie. Cher's budding romance with Josh (Paul Rudd) still seems questionable, at best, but the seeds of chemistry that are planted throughout complement the other plots. A lesser filmmaker would only be able to stick with one path, but Heckerling uses a stellar supporting cast to allow us to invest in several plots of varying nature.
Clueless is not trying to say anything too deep. I mean, the title says it all. But like Cher, it's a ditzy movie that is disguised as something more meaningful. With memorable quotes, scenes and costume design, it's pure fun. And sometimes that's harder to pull off than being so serious all the time.