When Clueless debuted in theaters in 1995, the filmmakers and cast were probably, well,
clueless about just how much of a classic the teen dramedy would instantly become.
The quirky coming-of-age tale of an upper crust debutante and her pals was a trendsetter
in fashion, lingo, and attitudes alike.
And it holds up as a fun piece of '90s iconography that reminds audiences of a simpler, albeit
snappier, time.
"I thought it reeked."
"I believe that was your designer imposter perfume."
But no matter how many times you've seen Clueless in the two decades since it dropped, there
are some things that even Cher Horowitz's most faithful fans might not know.
Here's a look at the untold truth of Clueless.
Literary inspirations
Writer-director Amy Heckerling has long maintained that Clueless is a modern retelling of Jane
Austen's novel Emma.
Fascinated with the social mores depicted in the novel, Heckerling pulled Austen's cast
of characters and basic plotlines and dropped them into the contemporary setting of Beverly
Hills High School, circa 1995.
Cher's well-intentioned but misguided attempts at matchmaking closely parallel Emma's journey
into young adulthood.
Clueless reminds us that learning to navigate the world of gossip, social hierarchy, courtship
are timeless rights of passage.
What people might not know is that her inspiration didn't come from just one source.
Heckerling also drew from the comic novel Gentlemen Prefer Blondes by Anita Loos when
it came to shaping the characters in Clueless.
As she told Jen Chaney, author of As If!: The Oral History of Clueless,
"I remember reading Emma and Gentlemen Prefer Blondes.
Those characters: what I gravitated to was how positive they could be."
Small screen start
While the movie eventually did have a television spin-off, Clueless was originally conceived
as a TV show.
In the early '90s, Amy Heckerling — who was best known for directing the movie Fast
Times at Ridgemont High — began development on another project that also centered around
Southern California teens.
Originally called No Worries, the concept soon moved from television to feature film
and was eventually renamed Clueless.
Could you imagine Clueless as anything other than the one hour, forty-five minute-long
movie perfection that it was?
"Ugh, AS IF!"
Moniker mistake
Eagle-eyed Clueless fans have noticed a pretty major flaw in the movie when it comes to the
matter of Cher's name.
While she answers to Cher Horowitz in class, her report card reads Cher Hamilton, and her
father receives a letter addressed to Melvin Hamilton instead of Mel Horowitz.
So what's with the name change?
There's speculation that the goof is a shout out to Heckerling's directorial film debut,
Fast Times at Ridgemont High.
The classic teen comedy stars Jennifer Jason Leigh as Stacy.
Her last name?
Hamilton.
The ick factor
Studio bigwigs were reportedly worried that the budding step-brother/step-sister romance
in Clueless would be a tad too icky for audiences to stomach.
"I had an overwhelming sense of ickiness."
But Heckerling insisted how the lead characters should connect.
The step-sib love story actually made perfect sense to Heckerling — because it happened
in real life for her grandparents, who met when they were teenagers.
"And suddenly.
Oh my God.
I love Josh!"
Costuming win
You can't talk about Clueless without talking about the fashion.
The well-planned-out costumes were the brainchild of costume designer Mona May, who counts Clueless
as her first feature film.
May pulled together looks for each character based on their personalities.
For Cher, each outfit was specifically chosen to highlight her character's growth throughout
the movie.
Meanwhile Dionne rocked sassier designs like leopard prints and bold colors, which reflected
her ascension into sexuality and womanhood.
So, there was a lot of thought that went into making the Cherwear so darn cute and fashionable.
"Thank you very much."
But not everyone was a fan of the fashion focus of the film.
In fact, Alicia Silverstone herself confessed that she thought being fitted for so many
outfits was annoying and pointless.
Silverstone told xoJane that she "had to endure something like 67 outfit changes" as she transforms
from self-absorbed teen to a slightly more self-aware young adult.
It really was all about the fashion, even down to the backdrop.
According to production design, the scenery was purposely kept drab and muted to ensure
the clothes popped.
Designer redux
A lot of designers earned some shoutouts through Clueless ...
"Oh no.
You don't understand.
This is an Alaiah!"
"An a-what-uh?"
"It's like a totally important designer."
And at least one designer took advantage of being name-dropped by the flick.
The little white mini Cher wears on her first date with Christian was, she explained, a
dress by Calvin Klein that prompted a classic father-daughter debate over what constitutes
wearing actual clothing — as opposed to parading around in your underwear.
As a result of the movie mention and its continued popularity even years later, the fashion house
ultimately reissued the dress in 2010.
Cast sliding doors
Hard as it is to imagine anyone else playing Cher, tons of soon-to-be famous stars also
auditioned for the part.
In fact, future vampire slayer, Sarah Michelle Gellar almost landed the role, while Reese
Witherspoon, Keri Russell and Tiffani Thiessen and were all in contention to play the fashion-obsessed
Beverly Hills teen.
Ultimately, it was Alicia Silverstone's appearance in the Aerosmith video for "Cryin'" that won
over the film's writer-director.
Heckerling would later explained,
"That was the first video she was in.
And I just fell in love with her."
The part of Cher wasn't the only one that was competitive for castmates.
Travis Birkenstock, the lovable stoner who skates away with Tai's heart was almost played
by Seth Green before it was ultimately given to Breckin Meyer.
Luckily, the two were close pals and didn't let the competition interfere with their friendship
afterward.
Meanwhile Dionne's white floral crocheted beanie was almost filled by former Fugees
member, Lauryn Hill, and none other than legendary comedian Dave Chappelle was considered for
the part of Murray — before Donald Faison nabbed the job.
Chapelle impressed Heckerling, but was a bit too jaded to pull off naive high school goofball.
She told The Hollywood Reporter, "He was just amazing — he was such a mensch [but] I needed
somebody who was really innocent, a goofy kid."
Rolling with the homies
Even two decades after its initial release, it seems like we still can't get enough of
Clueless — there's even a musical that's been in the works since 2012.
According to Heckerling, Clueless the Musical will use classic songs from the '90s to tell
the story and reaffirm, once again, its forever status as a staple of its generation.
We can probably already predict one song that'll make the playlist ...
"Rolling with the homies."
"Rolling with the homies!"
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