1.
Writer/director Amy Heckerling originally pitched Clueless to Twentieth Century Fox as a TV series called No Worries — but the executives thought it “needed more boys”.
2.
Even when working on it as a movie, it took awhile to settle on the title Clueless. Before that, Amy Heckerling used the titles I Was A Teenage Teenager and later Clueless in California.
3.
Cher was partially inspired by Jeff Spicoli from Fast Times at Ridgemont High, which Amy Heckerling also directed. She recognised he was the most popular character she’d created and decided that that was because he’s “positive”, so she wanted to create a lead who was positive and happy — which became Cher.
4.
It was when she was re-working the idea from a TV show to a movie that Amy Heckerling revisited Jane Austen’s Emma and realized Cher was basically a modern Emma, and she could base the plot of Clueless on Jane Austen’s novel.
7.
Ben Affleck and Zach Braff both auditioned for the role of Josh, as did Jeremy Sisto, who got the role of Elton, and Justin Walker, who went on the play Christian.
8.
Before being cast as Josh, Paul Rudd originally asked to read for the role of Murray, not realising the character was black and thinking he was a “white guy who’s trying to co-opt black culture”. He also read for Christian and Elton before Amy Heckerling suggested he try Josh.
9.
Seth Green — who is Breckin Meyer’s best friend — was the other top choice for Breckin’s role of Travis.
10.
And Terrence Howard, who is close friends with Donald Faison, was a top contender for the role of Murray.
12.
Sarah Michelle Gellar was offered the role of Amber, but couldn’t get out of her obligations to All My Children, which she was working on at the time.
13.
Alicia Silverstone thought Cher was a “materialistic, annoying little bitch” when she first read the script. She changed her mind when she realised how much Cher cares about her dad and other people.
16.
Before making Clueless, Jeremy Sisto had previously worked with Alicia Silverstone on a movie called Hideaway — he played a serial killer who goes after her character.
17.
Amy Heckerling based the role of Mr. Hall on a friend of hers who was a teacher, who helped her observe real classes while she was working on the script, and even had a cameo as the principal in the final movie.
18.
But she always had Wallace Shawn in mind to play Mr. Hall — and he was actually a teacher for three years in real life.
19.
Amy Heckerling had a cameo as a bridesmaid for Miss Geist’s wedding to Mr. Hall — she is best friends with Twink Caplan, who played Miss Geist, in real life.
20.
Amy Heckerling borrowed the unique slang used in the movie from a bunch of places, including real teens at Beverly Hills High School and those auditioning for the movie, the castmembers and crew, the queer community, and, of course, her own brain.
21.
Executives wanted Josh and Cher to be next-door neighbours because they thought the ex-step-sibling relationship was “too incestuous” — but Amy Heckerling pushed back, arguing (truthfully) that her own grandparents had been step-siblings who met as teenagers.
22.
Breckin Meyer sprained his ankle while rehearsing one of the skateboarding scenes, and subsequent scenes that featured him had to work around the fact he couldn’t really walk.
23.
A fake, cardboard credit card was used for the “suck and blow” scene because some of the actors couldn’t “suck” on a real credit card long enough to film their shots.
24.
While filming Clueless, Paul Rudd’s real life echoed the movie in a scary way — like Cher, he was robbed at gunpoint after he’d been out with a friend one night.
25.
The “This is an Alaïa” dress wasn’t originally part of the script — the dress was chosen first, and then written in.
27.
Paul Rudd wore a lot of his own clothes to play Josh — including the Amnesty International t-shirt.
28.
Donald Faison didn’t actually have braces in real life — he wore them as Murray to hide an extra tooth he had (a baby tooth that had never fallen out).
29.
The hairclip Cher wears in the concert scene was later used on Amanda Bynes’ character in She’s the Man.
30.
Clueless costume designer Mona May later worked on Romy and Michele’s High School Reunion, which she described as a “grown-up” version of Clueless, aesthetically.
31.
For the iconic opening looks Cher and Dionne wear, the plaid suits were meant to be reminiscent of schoolgirl uniforms, while the over-the-knee socks were inspired by Cabaret.
33.
Two extras were randomly paired to makeout for a party scene — they later went on to get engaged in real life.
34.
Paul Rudd gave everyone one of those necklaces with their name written on a grain of rice as a farewell gift when shooting wrapped.
