For some people, the idea of a teen movie is synonymous with the 90s. The movies made in the last decade of the 20th century had the benefit of being influenced by greats like John Hughes films and Heathers. They also had the benefit of taking place in an era were people were a lot more open to the idea of teenagers having sex. This created some interesting characters, stories and unforgettable movies.
10. American Pie- For some, this is the 90s sex comedy. While it isn’t the best film ever made, and it spawned some pretty damned awful sequels, American Pie is still pretty iconic. “This one time at band camp…” is the sexual joke of a whole generation.
9. Romeo +Juliet- Baz Lurhman’s version of the classic Shakespeare play is very 90s. But it is also well-acted (featuring Leonardo DiCaprio at the height of his heart-throb status), and visually stunning. It also handles the source material an a creative way and manages to keep it fresh.
8. Can’t Hardly Wait- What seems like it’s going to be a cliched film about having one last night of fun before the end of high school, actually ends up being surprisingly funny, touching and smart. While it is still pretty cheesy, it also has some memorable moments a great scenes. You will never hear “Paradise City” without thinking of this movie again.
7. Election- This Alexander Payne film is a great satire of the politics surrounding both the adults and the teens in high school. It uses the class president election as a frame, but the politics go way beyond that. The film becomes about sexual politics and gender politics and the politics of ambition.
6. Cry-Baby- The John Waters musical is a great send-up of the 1950s rock and roll subculture. The film, starring Johnny Depp, also pokes fun at the idiotic weight that teenagers put on their every feeling. Cry Baby Walker’s feelings are overdramatic in the most hilarious way, and the soundtrack is awesome.
5. Rushmore- Wes Anderson’s second film, Rushmore, is admittedly not my favorite of his movies. But it is one of the best high school movies ever made. Max Fisher’s (Jason Schwartzman) overblown sense of his abilities and the possibilities around him are at once completely ridiculous and totally relatable.
4. But I’m A Cheerleader- This indie film is super important. The story of a young girl who gets sent to a “rehab” facility that is supposed to keep her from being a lesbian. It is a story of self-discovery, a touching loving story, and a great satire of traditional gender roles and society’s expectations on its teenagers. It stars Natasha Lyonne of Orange is the New Black.
3. 10 Things I Hate About You- This movie is a classic for a reason. It is totally cheesy, and in some ways a complete paint by numbers high school romance movie. But it also features an awesome heroine in Kat Stratford (Julia Stiles) and one of the first great performances of the late Heath Ledger. It also has some great lessons in it about being yourself and not doing things to impress other people.
2. Cruel Intentions-Like 10 Things I Hate About You, Cruel Intentions is based on a work of classic literature. But instead of Shakespeare, it’s based on the steamy novel Les Liasons Dangereuses. The French story of sexual intrigue works surprisingly well in a preppy high school setting. So well in fact that it is classic. The movie also features performances by 90s greats like Reese Witherspoon, Ryan Phillippe , Selma Blair, and (my favorite), Buffy herself, Sarah Michelle Gellar.
1. Clueless- But if there is any movie that beats the 90s classic status of Cruel Intentions, it is Clueless. Yet another literary adaptation (those were seriously popular), Clueless is a modern retelling of Jane Austen’s Emma. Arguably one of Jane Austen’s best books, Emma is the story of a young girl who tries to play matchmaker. Clueless takes that same story and gives it a 90s valley girl spin. The script is hilarious and the acting is pretty funny as well. Overall Clueless is the most 90s movie I can think of, and that alone makes it worth being in the number one spot. But even without all the 90s goodness, it’s also pretty classic, and really funny.