Director: Amy Heckerling
Stars: Alicia Silverstone, Stacey Dash, Brittany Murphy
Plot: Cher is rich, pretty, blonde, popular and knows how to talk anyone into doing just about anything. When she can't get a teacher to give her a better grade, she and her friend Dion match him up with another teacher to make him happier... and maybe a but laxer on his expectations. When a girl named Tai transfers to Cher's school, she and Dion give her a makeover and attempt to find her a boyfriend. Cher soon realizes that she wants a boyfriend herself, but no one seems right. She goes through a spiritual makeover and realizes that there's more to life than clothes and popularity before she finds the boy of her dreams.
During the game of "Suck and Blow," the cast was unable to sustain the breath to make a real credit card pass from mouth to mouth; a prop card made of cardboard was substituted that still did not work. Holes were drilled into it to make it easier, and when this failed also, the whole cast's lips were heavily coated in chapstick to force the card to stick.
Alicia Silverstone (Cher) actually did not know how to correctly pronounce "Haitians" in the classroom scene. Director Amy Heckerling told the crew not to correct her because she liked it so much and wanted it to be in the film.
The film's writers sat in classes at Beverly Hills High to get the flavor of the students.
Alicia Silverstone did not have to audition for her role in this movie.
Plot, Characters, Themes and Values are all based on Jane Austen's novel [Emma]. Amy Heckerling was asked by Paramount to write a film for teenagers, and she instantly remembered the novel she read as a teenager.
While filming, Paul Rudd was mugged and had his backpack stolen, which held his script for the movie.
According to the script for Clueless (1995), the restaurant scenes were supposed to take place at California Pizza Kitchen, but when the CEOs of that franchise read the breadstick/penis jokes in the script, they would not allow filming to take place in their restaurants.
In the scene where Cher is packing for her father and is surprised by Christian's call, he is at a museum. The painting behind him is of two men affectionately in an embrace, another foreshadow of his sexuality.
The films that Christian watches on video with Cher, Some Like It Hot (1959) and Spartacus (1960), provide clues to his sexual orientation. The first movie deals with cross-dressing men (who are escaping from a mob hit). The second includes the famous scene where a Roman master (Laurence Olivier) tries to seduce his male servant (Tony Curtis).
The book Christian is reading during class, "Junky" by William S. Burroughs, is another clue and indication of his sexual orientation, as its author had strong homosexual desires.
The scene where Cher wanders around and realizes her true feelings for Josh as fountains erupt is borrowed from Gigi (1958), where Gaston does the same thing. The music playing when Cher stands at the top of the stairs in her white dress before her date with Christian is taken from the same movie. Gigi, incidentally, wears a white dress both times that particular theme is played.
DIRECTOR_CAMEO(Amy Heckerling): makes a cameo as Miss Geist's maid of honor at the wedding scene. She is also in the bouquet catching scene and is the source of most of the struggling.