1995 – Clueless

Paul as Josh
Directed by: Amy Heckerling
Written by: Amy Heckerling
Produced by: Barry M. Berg, Twink Caplan, Robert Lawrence
Production year: 1994
Original release: July 19, 1995
Running time: 1 hour, 40 minutes
Other cast: Alicia Silverstone, Stacey Dash, Brittany Murphy
Misc: IMDB | Amazon | iTunes

Shallow, rich and socially successful Cher (Alicia Silverstone) is at the top of her Beverly Hills high school’s pecking scale. Seeing herself as a matchmaker, Cher first coaxes two teachers into dating each other. Emboldened by her success, she decides to give hopelessly klutzy new student Tai (Brittany Murphy) a makeover. When Tai becomes more popular than she is, Cher realizes that her disapproving ex-stepbrother (Paul Rudd) was right about how misguided she was — and falls for him.