Clueless began as a TV series.
No, we're not talking about the spinoff TV series, which ran from 1996 till 1999, with most of the cast reprising their roles, minus, of course, Alicia Silverstone. Amy Heckerling, who directed National Lampoon's European Vacation, Johnny Dangerously, Fast Times at Ridgemont High and a few episodes of its short-lived TV spinoff, initially pitched Clueless as a teen soap series in the vein of Beverly Hills, 90210. The show would have been called No Worries. Heckerling figured Jeff Spicoli was so popular because he was always so positive, so she decided to create a character with that same personality trait. Cher was born. As No Worries evolved from the initial TV series idea, the name was changed to I Was a Teenage Teenager. Then it became Clueless in California, which was eventually shortened to Clueless.
Clueless owes much to Jane Austen.
Several years before Pride and Prejudice and Zombies, Heckerling borrowed elements of a classic Jane Austen story and repurposed them for modern times. The title character in Emma, which reminded Heckerling of old TV shows like Gidget when she read it in college, inspired Cher. Most of the rest of the characters have counterparts in Jane Austen's story, too; Dionne is Isabella, Tai is Harriet, Josh is George, Elton is Philip Elton, and so forth. Heckerling spent some time at Beverly Hills High School, listening to how contemporary teenagers spoke. She invented some slang of her own, too, like the idea of "Betties and Baldwins" - which itself inspired an English hair salon situated on Small Street in the Old City area of Bristol.
Josh and Cher owe something to the director's family, too.
Cher ends up with Josh, whose mother was briefly married to Cher's dad. The whole stepsibling romance didn't seem crazy to Heckerling, because she was well acquainted with a couple that'd lived it: her grandparents. They were a stepbrother and stepsister who were teenagers when their widowed parents got married.
Reese Witherspoon auditioned to play Cher.
According to a richly detailed Entertainment Weekly story and the fantastic book As If: The Oral History of Clueless, by Jen Chaney, a number of actresses tried out for the lead role, including Reese Witherspoon. It was reportedly offered to Sarah Michelle Gellar, who declined because of her shooting schedule with All My Children. Heckerling says a casting-director pal suggested "the girl from The Crush," but she was more interested in getting "the girl from the Aerosmith videos." When she finally watched The Crush, she realized they'd been talking about the same person.
Lauryn Hill and Terrence Howard auditioned, too.
Stacey Dash, who at 27 was the oldest of the actors playing teenagers, read with Terrence Howard before she was paired with Donald Faison. Before meeting Dash in Los Angeles, Faison had read with Grammy winning musician Lauryn Hill in NYC.
There's a Perfect Strangers connection.
While Clueless was in production, Heckerling was dating Bronson Pinchot, star of the hit sitcom Perfect Strangers. The fictitious Bronson Alcott High School was partly named for him and presumably named for Amos Bronson Alcott, a 19th century writer, Abolitionist and vegan. (Alicia Silverstone is now vegan herself.)
Two Clueless castmembers actually went to Beverly Hills High.
Beverly Hills High School served as the location for Bronson Alcott High School in Clueless. Not only was it the same high school where Heckerling had done some of her research - both Alicia Silverstone and Breckin Meyer had been students there.
Rollin' with the Homies...
Who can forget "Rollin' With the Homies," the '90s single with a special romantic connection for at least one Clueless character? The Clueless Oral History revealed that it was actually Coolio himself who suggested the song for the movie. Impressively, actor Jeremy Sisto came up with the "Rollin' With the Homies" dance.
The CGI clog.
The clog that knocked out Elton's dance partner wasn't real. Sure, there was a prop clog used during filming, but the shoe that audiences saw hitting Brittany Murphy in the head was added in post, as the prop clog simply didn't look convincing.
The clothes, the clothes, the clothes.
Speaking of fashion, there are said to be more than 50 different types of plaid throughout the movie, seven of which are on Cher alone. In fact, Cher changes her clothes 60 times in Clueless. Her white dress stayed so popular, Calvin Klein reissued it in 2010. First time Costume Designer Mona May avoided dressing characters in all black, opting for fun and colorful designs instead. The hard work paid off: after Clueless, she worked as Costume Designer for movies like Romy & Michelle's High School Reunion, The Wedding Singer, Never Been Kissed, and Enchanted.