The best teen movies are the ones that transcend their genre and generations. Regardless of our age and how old we were when these movies were released, we can still relate to them.
Two of my favorites are based in classic literature, Taming Of The Shrew by William Shakespeare and Pygmalion by George Bernard Shaw. They were also rebooted into Broadway musicals, Taming Of The Shrew remade into Kiss Me, Kate and Pygmalion remade into My Fair Lady.
10 Things I Hate About You is the story of the Stratford Sisters. Biana (Larissa Oleynik) is extremely eager to be popular and date Joey Donner (Andrew Keegan). But her hilarious and cringe inducing overprotective father (Larry Miller) will not allow Bianca to date until her older sister Kat (Julia Stiles) is dating. Kat has no interest in dating anyone. Cameron James (Joseph Gordon-Levitt) is new to the school and falls in love with Bianca instantly. He uses Joey, who pays Patrick Verona (Heath Ledger), to date Kat, so he can go on a date with Bianca. The end result is very interesting and very entertaining.
I love this movie. The screenwriters kept the Beatrice and Benedict relationship between Kat and Patrick (as well as some of the Shakespearean language from the play) while dulling the sexist and misogynistic language of the original text. The late Health Ledger (pre Batman and pre Oscar for Brokeback Mountain) has a massive potential as an actor, that potential shines through in his later roles. Julia Stiles is another up and comer who proves that she has the talent to go very far.
She’s All That starts at the tail of senior year. Popular Zach (Freddie Prinze Jr) has just been dumped by his girlfriend (Jodi Lyn O’Keefe). Zach’s friend Dean (the late Paul Walker), makes a bet that Zach can turn any of his female classmates into prom queen. Zach’s choice is Laney (Rachael Leigh Cook), the artsy outsider.
I love this movie. It’s one of those movies that I can find on cable and brought back to that time in my life. The coup that makes this movie stand out from other teen movies of this era is that Zach and Laney are each dealing with their own internal pressures. As their relationship grows, they find a way to deal with those pressures. This is another movie full of then up and coming performers (Usher, Gabrielle Union (who also had a part in 10 Things I Hate About You), Anna Paquin, Dule Hill) who have had steady careers since then.
Both of these movies have quotable lines and soundtracks that fit in so perfectly with era that they premiered.
I recommend them both.