Clueless (Amy Heckerling, 1995)
Adapted from Emma by Jane Austen
While the plot of Clueless might slightly defer from the original novel by Jane Austen, the strong minded, determined heart of Emma can clearly be found in spoilt Beverley Hills teenager Cher, whose matchmaking plans – like Emma’s – lead to much trouble. Due to the strong characters, fabulous outfits, and hilarious teen slang, Clueless still remains a cultural phenomenon 25 years later.
Romeo + Juliet (Baz Luhrmann, 1996)
Adapted from Romeo and Juliet by William Shakespeare
Unlike the other films on this list, Luhrmann’s adaptation largely stays loyal to the play’s original text – however, interestingly switching the location from Verona, Italy to Verona Beach, USA. While not strictly a teen movie, the casting of Leonardo DiCaprio got many a teen heart racing back in the ’90s. R+J also features a rousing portrayal of Mercutio by Harold Perrineau.
Cruel Intentions (Roger Kumble, 1999)
Adapted from Les Liaisons Dangereuses by Pierre Choderlos de Laclos
Moving it’s location from pre-revolution France to New York’s Upper East Side, this seductive teen drama, which starred Sarah Michelle Gellar and Ryan Phillippe, was just as dramatic as the original novel, and almost as scandalous.
10 Things I Hate About You (Gil Junger, 1999)
Adapted from The Taming of the Shrew by William Shakespeare)
A fan favourite from a time when teen Shakespeare adaptations were being released nineteen to the dozen, this quirky comedy drama – which was set in an American high school – remains just as popular today, due to the energetic ensemble cast and witty dialogue. It’s hard to believe that the late Heath Ledger’s performance as Patrick Verona was filmed less than ten years before his career high portrayal of The Joker in The Dark Knight.
The Half of It (Alive Wu, 2020)
Adapted from Cyrano de Bergerac by Edmond Rostand
Cyrano de Bergerac is clearly a director’s favourite of classic plays, as Netflix alone hosts countless modern interpretations. Low-key teen drama The Half of It is one of the better (albeit very loose) adaptations, subverting the original plot so that the lead character is the same gender as the girl they are crushing on. Advertised as a LGBT teen movie, THOI is also a lovely coming-of-age story about friendship and family.
O (Tim Blake Nelson, 2001)
Adapted from Othello by William Shakespeare
A darker item of this list, O‘s setting is (once again) an American high school, this time centring around a basketball team. As in the original, O, which stars 10 Things I Hate About You‘s Julia Stiles, features strong themes of jealousy and manipulation, with a suitably grim ending.
Easy A (Will Gluck, 2010)
Adapted from The Scarlet Letter by Nathaniel Nawthorne
This witty comedy both embraces and parodies the genre of teen movies, also somewhat breaking the fourth wall by having the lead character, Olive, openly imitate features of the original novel – wearing corsets adorned with a red ‘A’ while classmates gossip about her sex life. Easy A gives a more feminist, sex-positive take than most teen movies, and includes a sensational lip sync of Knock on Wood that Ru Paul would be proud of.