Clueless (1995)

Amy Heckerling loosely moved Jane Austen's Emma to a Beverly Hills high school, and the result is the smartest "dumb" comedy ever made about a rich girl learning she is not the center of the universe. Alicia Silverstone's Cher is a meddling matchmaker who is somehow lovable rather than insufferable, which is the whole trick of Austen's heroine too. Adults will catch how much the film knows about its world, and how its affection for every character never curdles into mockery. The one wrinkle that reads differently now is that Cher's eventual love interest is her former stepbrother, played by Paul Rudd, though the film treats it lightly.