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It’s hard to believe it’s been more than20 yearssinceCluelessmade its debut in theaters.
The quirky coming-of-age teen comedybecame an instant cult classic.

Today,Cluelessis a virtual time portal to all the hipness 1995 had to offer.
Gentlemen Prefer Blondes was also an influence
Inspiration didn’t come from just one source.
Heckerling drew from the comic novelGentlemen Prefer Blondesby Anita Loos when it came to shaping the characters inClueless.

Asshe told Jen Chaney, author ofAs If!
Originally calledNo Worries, the concept soon moved from television to feature film and was eventually re-namedClueless.
While she answers to Cher Horowitz in class, her report card reads Cher Hamilton.

In addition, her father receives a letter addressed to Melvin Hamilton, not Mel Horowitz.
So what’s with the name change?
The well-planned-out costumes were the brainchild of costume designer Mona May, who countsCluelessas 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.
It influences everything from character development to the set design.

But not everyone was a fan.
Alicia Silverstone confessed that she thought being fitted for so many outfits was annoying and pointless.
But not everyone was a fan of the focus on fashion.

The dress wasreissuedby the design house in 2010.
It’s hard to imagine anyone but Alicia Silverstone as Cher Horowitz.
However, there was a bevy of soon-to-be famous actors who auditioned for the part.

Future vampire slayer, Sarah Michelle Gellaralmost landedthe role.
And Gellar wasn’t the only future A-list actor considered for the lead.
Reese Witherspoon, Keri Russell and Tiffani Thiessen andwere all in contentionto play the fashion-obsessed Beverly Hills teen.

But for Heckerling, the lead was a clear choice thanks to a music video.
“I was watching an Aerosmith video of ‘Cryin’,“explained Heckerling.
“That was the first video she was in.

And I just fell in love with her.”
Instead, the part went to his close friend, Breckin Meyer.
In an excerpt from Jen Chaney’s book,As If!

And it turned out they were best friends….
But I’m sure each wanted the part.”
Dash portrayed Cher’s fashionable partner in crime in the movie and reprised the role in theCluelesstelevision series.
But Dionne’s white floral crocheted beaniewas almost filledby former Fugees member, Lauryn Hill.
Chapelle impressed Heckerling, but was a bit too jaded to pull off naive high school goofball.
At the 1996 MTV movie awards, three of the Golden Girlspaid homagetoCluelessby spoofing the film.
In 2015, the bookAs If!