The 1995 film Clueless is one that remains popular today. You would be hard pressed to find people who haven’t seen the film even just once. The odd thing, though, about the film, is that it is incredibly dated in terms of slang, clothing, and technology, but it’s had a long lasting societal impact. 

Now, I’m not a fan of Jane Austen’s book Emma. However, to my understanding, Clueless is an excellent modern retelling of the story. And kudos to Amy Heckerling for that because adapting a classic novel is no easy feat. 

The film itself is very much a “90s” film. It is filled with now outdated fashion (even though the 90s keep trying to sneak back up on us on the Target clothing racks), outdated technology, and phrases like “way harsh”and “as if”, and even a mention of Marky-Mark. But, the film dates itself in negative ways, as well: referring to Christian as a “cake boy” and the use of the word “retard” are especially cringy. 

Speaking of cringy, I need to talk about that kiss. And, you know what kiss I’m talking about. 

Cher and her ex-step-brother become romantically involved, and I am always, always, always very conflicted about it. It’s not technically wrong. Cher’s dad was married to Josh’s mom for a while, which made them step siblings. Cher’s dad and Josh’s mom then divorced, severing that sibling relationship, but Josh still spends time at the house he spent years in. That seems pretty normal, I think. And, again, there is no relation between Cher and Josh, so it’s not technically “wrong” in that way. However, there is also the question of ages. Cher is 16 years old. Josh is a college freshman, making him 19, at the oldest, which is only a 3 year age difference. Again, not necessarily wrong, but it feels wrong. It all feels wrong. But, Paul Rudd, who plays Josh, and Alicia Silverstone, who plays Cher, have such great chemistry together that it makes me root for them. I’ve been endlessly conflicted about this match up ever since I first saw the film and I will continue to be conflicted about it for the rest of my life, I’m sure. 

I find it so interesting that this film has had a lasting cultural impact. As I stated before, it’s dated in a number of ways. And, yet, it continues to be present in the year 2020 (The 25th anniversary is this year and, pre-stay-at-home order, there were showings scheduled as a celebration in Los Angeles). I keep racking my brain to figure out why this film, being among so many other teen rom-coms in the 90s, is the one that has stood the test of time. I think I’ve narrowed it down to a few main things. The story of Emma is a timeless one. Every teenager can find some aspect of that story to relate to. Amy Heckerling did a phenomenal job of updating the story just enough and the cast of the movie has chemistry. Everything feels very natural. 

I feel like this film has become a time capsule, of sorts. To those that saw it in the 90s, it carries a sense of nostalgia. To those that saw it later, the film feels like it’s frozen in time, in the best way possible, as the most idealistic representation of the 90s decade. 

Also, quick shout out to Donald Faison for one of my favorite line deliveries of all time.