Clueless: A Sharp, Funny, and Surprisingly Smart Teen Classic

Ms. Stoeger, my plastic surgeon doesn’t want me doing any activity where balls fly at my nose.
There’s a sea of dumb teen movies. Many of these even portray characters that are supposed to be smart. We know this because other characters constantly refer to them as smart, even though their actions don’t really reflect this. For a long time, I assumed Clueless was one of these films. It wasn’t until a few weeks ago that I saw this film, at the insistence of my podcast co-host Maria, and I was pleasantly surprised. This is very nearly the exact opposite of the trope I just described. The characters are surprisingly smart, although other characters tease them for being dumb. Written and directed by Amy Heckerling (Fast Times at Ridgemont High, Look Who’s Talking) and starring Alicia Silverstone, Paul Rudd, and Brittany Murphy, this is a surprisingly sharp teen comedy based on Jane Austen’s Emma. The dialogue is witty, the characters are well-fleshed-out, and the film has some great things to say about women in society without forcing the statement to the detriment of the plot. This is undoubtedly one of the classic teen films of the 90s, and one of the smarter films in the genre, and it still deserves attention today.
The plot follows Cher, an attractive and independent young woman from a rich family, and centers on her group of friends, including her best friend Dionne and a new student name Tai, whom Cher and Dionne adopt to teach her about beauty and polite society. Cher is used to getting her way with everything, even if she has to work for it. She negotiates higher grades with her teachers; she’s able to buy pretty much anything she wants, even if that means she has to take care of her constantly-working single father; she has the friends she wants, even if she has to train them to be as cool as she is. As Cher matures, she begins questioning what she would look for in a romantic relationship, as well as her own intentions in trying to shape and define the people around her. Will she ever be more than a clueless young woman? Many in her life tell her no, but she seeks a deeper answer.
He does dress better than I do. What would I bring to the relationship?
For all of the talk about clueless, shallow teenagers, this film and its characters are actually rather smart. As my podcast co-host Maria pointed out, Cher’s insight about Amber being like a Monet painting is not an observation a dumb person would make. Cher is inexperienced and naive, but she is not dumb or entirely selfish. Many of the lines in this film are witty and memorable, and Alicia Silverstone does a great job bringing this complex independent young woman to life. Also, Brittany Murphy stole the show with the adorably awkward Tai. Be warned that the dialogue in this film is probably the most 90s ever—so much so that a book was later published instructing readers on how to talk like the characters in this film. As someone who went to high school in the 90s, I won’t say that this is entirely accurate, but the characters and dialogue in this film are definitely the epitome of 90s teen culture, and I mean that in the best way possible.
Clueless also has some great things to say about women in society. The film focuses on the female characters and their relationships with each other—something rare for many movies, but especially teen movies. It doesn’t shy away from showing us the hardships of being a woman. Teenage guys can be creeps, and Cher has to deal with that in not-so-comical ways. Men are constantly telling Cher she’s dumb and shallow, even when that reputation is not earned. In her single-parent household, Cher functions as both a mother and a wife in taking care of herself and her father, but gets absolutely no credit for that. Perhaps most surprising about this film, though, is that it celebrates both feminism and traditional femininity, and very few films will do justice to both. Is it alright for a strong female character to also love shopping and beauty? Yes, absolutely! This is one of the more profound points the film makes.
For all the depth here, though, the film is, first and foremost, entertaining. It’s very funny and goes way beyond the cheap gags that plague other teen comedies. There are a few jokes that touch on how out of touch these rich, privileged teenagers are with what regular teenagers have to deal with, such as when Cher claims she doesn’t need to know how to park a car because everywhere has valet, but for a film about the richest, most popular kids in school, these characters are surprisingly real and relatable. Much like its source material, the film also pokes fun at the day’s social customs, many of which are still in practice in 2019.
Should I Watch Clueless?
Is Clueless the perfect 90s teen film? Well, Ghost World certainly gives it a run for its money (despite being released in 2001), but this is certainly the best 90s teen film on my list. This is a smart comedy that comments on the role of young women in society without forcing an agenda, and it features some really well-written characters that I genuinely enjoyed watching—a real feat, since virtually all the 90s teen films I grew up with trained me to hate the popular kids. If you haven’t seen this one and enjoy teen films, this is a must-see film. I’ll say I enjoyed it a lot more than I thought I would and was surprised by the film’s intelligence and wit.
Movies Like Clueless
- 10 Things I Hate About You (1999) - An updated retelling of Shakespeare’s The Taming of the Shrew, 10 Things blends sass and sincerity for a story that’s quirky, surprisingly feminist, and quintessentially 90s. Like Clueless, the women are strong and live for more than the male characters. Julia Stiles and Heath Ledger really sell their characters: an antisocial older sister to the most popular girl in school, and an odd but charming man working hard to win her heart. If you like 90s teen comedies, this is one of the better ones.
- Mean Girls (2004) - A clever teen satire of a girl who unwittingly falls into a group of popular mean girls and then accidentally falls for one of their ex-boyfriends, Mean Girls picks up a torch from Clueless and runs with it. Teen comedies are not known for being smart, but comedy genius Tina Fey imbues this one with cleverness as well as effective comedy and quotable dialogue. Mean Girls has become a modern classic that is well worth watching for fans of Clueless.
- Legally Blonde (2001) - I hate to say this, as I famously hate Legally Blonde, but it’s a great spiritual successor of Clueless: a beautiful student who everyone has written off as dumb succeeds in her ambitions, proving all of her detractors wrong. Though the character Elle is intelligent and the story feminist, the film isn’t quite as smart as Clueless. It’s still worth a watch, though, if you’re looking for an empowering feminist story about women overcoming stereotypes without abandoning the femininity they enjoy.
- Runtime: 1:37
- Director: Amy Heckerling
- Year: 1995
- Genres: comedy, teen
- Rating: PG-13

About Brandon
My name is Brandon, and I love movies. Not bad ones, though—just the good ones. I’m curating and reviewing a list of classic, essential-viewing, or just plain good movies from all decades, and I've been reviewing them since 2016. I also co-host Peculiar Picture Show, a podcast about movies and mental health and write about Dungeons & Dragons options, builds, and optimization.
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