The classic teen comedy Clueless, directed by Amy Heckerling, stars Alicia Silverstone as Cher Horowitz, a Beverly Hills teen.
This 1988 dark comedy, directed by Michael Lehmann, follows Winona Ryder’s Veronica Sawyer as she navigates the treacherous social hierarchy of her high school, which is ruled by a clique of popular girls called Heather.
In 1997, Danny Boyle directed A Life Less Ordinary, a romantic comedy with fantasy elements. Ewan McGregor played a janitor, while Cameron Diaz played Celine Naville, a spoiled heiress.
The romantic comedy 10 Things I Hate About You was released in 1999 and directed by Gil Junger.