Clueless (1995)

Loosely based on Jane Austen's novel Emma, Clueless follows Cher Horowitz, a 16-year-old high schooler who's struggling with all the angst and drama and responsibility that comes with being a teenager — while living in Beverly Hills, wearing Armani and driving a Jeep. Cher (Alicia Silverstone) selflessly decides to help a dorky new girl (Brittany Murphy) become cool and popular, with unexpected results. But luckily her older, handsome stepbrother (played by Time Lord Paul Rudd) is there to help her get through it all.