Alicia Silverstone in ‘Clueless’

Alicia Silverstone (front and center) stars as Cher Horowitz in the 1995 smart high school comedy Clueless. She is joined by Stacey Dash (left, as Dionne) and Brittany Murphy (right, as Tai). The film, directed by Amy Heckerling, was a loose modern riff on Jane Austen's book Emma. Alicia Silverstone was born in 1976, so she turned 19 the year the film was released.