Clueless has managed to be a cultural influence for the past 20 years, it’s been an annual watcher for me throughout that time and that’s pretty incredible in all honestly. If you’ve watched it one too many times and you’re looking for something similar to fill that Clueless shaped hole, I think I can help you out.
It’s clearly a movie with the message that some things never change, no matter how old you are, but it’s lovable in all of the same ways Clueless is. The adorable Drew Barrymore masquerading as a high schooler is sure to quickly win you over.
This time our main character has to deal with Harvard sorority sisters and the struggle to establish personal independence, Legally Blonde carries all the same joy that we loved in Clueless.
Consider this a more sadistic version of Clueless. There are some of the same satirical jokes about female relationships in both movies, and they’re so similar yet very different at the same time.
If you love dark comedy, you’ll like this one all about doing away with high school bullies, one by one. The main character starts to despise her popular friend group clique, the Heathers, she joins up with a rebel loner and they decide to start offing the bullies at school.
The similarities aren’t obvious with this one and it’s mostly the writing style that ties both this and Clueless together. Andie is an outcast at her Chicago high school. When one of the rich and popular kids at school, Blane, asks Andie out, it seems too good to be true. As Andie starts falling for Blane, she begins to realizes that dating someone from a different social sphere is not easy.