20 Things You Probably Didn’t Know About Clueless

If you’ve never seen the classic coming-of-age comedy movie Clueless, then you really are missing out.

Telling the story of a popular high school student who befriends a new pupil and gives her a makeover, it really is one of the best movies of the 1990s, and below are 20 things you probably didn’t know about it.


20. It’s based on a Jane Austen novel

Clueless might seem like just another vapid teen movie, but its chief inspiration is actually pretty academic.

The plot is loosely based on Emma, a Jane Austen novel about a privileged but kind-hearted matchmaker whose schemes get out of control.

Like Cher, Emma has to learn that her meddling is not always wanted or needed, and instead channels her energy into becoming a better person.

These literary allusions can be seen in Cher’s own use of classic poetry to set up her two unhappy teachers.

Also, Jane Austen was famous for writing about the lives of women that other authors considered trivial or unimportant, so she’d probably be super into Clueless as a spiritual successor.

It wouldn’t be the first high school film to call on classic literature for inspiration. After all, 10 Things I Hate About You is based on Shakespeare’s The Taming of the Shrew!

19. Director Amy Heckerling sat in real high school classes to get the film’s slang right

Teen movies are hard to write, in part because teenagers are arguably the fastest-changing demographic on Earth.

In the time it takes to cast, film and release a movie, everything about teen culture could have already changed – from what clothes are in fashion to what slang people are using.

To avoid this problem as much as possible, the film’s director, Amy Heckerling, sat in real high school classrooms and observed how they talked, integrating the most up-to-date phrases into the script.

The director took inspiration from all different kinds of teenagers, taking expressions from different cliques and observing how they differed.

Cher’s iconic “as if!” in response to any kind of difficulty actually came from the LGBT community, with lesbians, in particular, popularising the phrase in various different high schools around America.

18. Reese Witherspoon almost played Cher

Credit: dtstuff9 via Flickr

Though Silverstone’s casting was locked-in pretty early in production, her taking the role of Cher wasn’t always a foregone conclusion.

At one point in the casting process, Reece Witherspoon seemed like the obvious choice, as she was likeable, experienced and, most of all, blonde.

Credit: Eva Rinaldi via Flickr

Witherspoon had proven she could play the kind of character the movie was going for, and at the time she had far more feature film credits to her name than Silverstone.

Thankfully, the studio’s ambivalence towards casting someone with any kind of star profile led to the virtually unknown Silverstone being picked.

Credit: Georges Biard via Wikimedia Commons

This gave Witherspoon the chance to play her own enterprising party girl turned activist a few years later, when she starred in Legally Blonde.

17. Buffy’s Sarah Michelle Gellar was also almost cast

While casting for Cher was still all up in the air, producers reached out to Sarah Michelle Gellar, who at the time was famous for being the biggest bad girl on daytime television.

This was down to Gellar’s stint as Kendall Hart on All My Children, the long-lost daughter of one of the show’s feistiest characters, who was furious at her abandonment and determined to get revenge.

Gellar had become a breakout star who was praised for her ability to remain likeable while making mistakes, making her perfect for Cher.

Unfortunately, once Gellar entered into negotiations for Clueless, it was realised that shooting would conflict with her existing shooting schedule for All My Children.

Gellar soon finished her run on the show to allow her to be in other projects – in part due to her having to turn down Clueless.

16. Jeremy Renner was almost the object of Cher’s affections

Credit: Eva Rinaldi via Flickr

Many future stars auditioned for Clueless, with Owen Wilson and Zooey Deschanel among those seen by casting.

This was due to the film having so many characters to cast and not much of a budget to speak of, which led producers to cast cheaper up-and-comers with potential instead.

Credit: Elen Nivrae via Flickr

Jeremy Renner was one of the on-the-rise actors who got the Clueless casting call. He went out for both the characters of Josh and Christian.

Renner ended up losing out for the part not just once, but twice, being passed over for both of the parts he auditioned for.

Credit: Eva Rinaldi via Flickr

This rejection quelled Renner’s interest in starring in teen rom-coms, and the future Marvel actor went on to seek out more challenging and controversial roles.

16. Alicia Silverstone was at the time best known for starring in Aerosmith videos

Although she had also appeared in the TV show The Wonder Years, Alicia Silverstone prior to Clueless was mainly known for starring in the music videos for Aerosmith’s songs Cryin’, Amazing and Crazy.

These music video appearances made Silverstone a name in Hollywood, and also gave her the nickname ‘the Aerosmith chick’.

Thanks to MTV, the Aerosmith music videos were impossible to avoid, and most teenagers could recognise the pretty blonde who starred in them.

That made Silverstone’s transition into teen movie star a pretty easy one, since Clueless’ unique lexicon and fashion also became part of teen culture pretty quickly.

Even now, most people can name Silverstone as the Aerosmith chick, even before they talk about her starring in Clueless.

15. The movie’s principal was a teacher in real life

If the bumbling but loveable principal in Clueless feels realistic to you, it’s because the actor playing him was drawing on some real-life experiences.

The actor who plays him, Herb Hall, is actually a drama teacher, who at the time had been teaching daily at a school for over a decade.

Until Clueless, Hall’s acting resume was mostly filled up with TV commercials and theatre work, rather than movies.

However, thanks to his position at Beverly Hills High School, the setting of Clueless, Hall was given the opportunity to star in the film in his first featured role.

Hall has continued to act, since appearing in the movie Closure in 2018, though he did recently retire from teaching after 28 years at Beverly Hills High.

14. The film was so successful that Alicia Silverstone was given a $10 million-dollar movie deal

Clueless was both a critical and commercial success, and led to Alicia Silverstone signing a deal with Columbia/TriStar reportedly worth around $10 million.

Silverstone went on to star in a number of different movies as part of the deal, including Le Nouveau Monde, Hideaway and The Babysitter.

However, most of the movies were not particularly successful, with True Crime, released in 1996, for one going straight to video.

Despite this, Alicia Silverstone also remained a household name and fashion icon, constantly being scrutinised and admired in turn for her red carpet choices.

In recent years, Silverstone has featured in everything from The Killing of a Sacred Deer to Diary of a Wimpy Kid, movies which are definitely not going straight to VHS.

13. One of the movie’s actresses died tragically

Brittany Murphy, who starred in Clueless as Tai Frasier, sadly met a tragic end at the age of 32 after developing pneumonia.

After Murphy’s death in 2009, Alicia Silverstone said “I loved working with Brittany. She was so talented, so warm, and so sweet.”

In 2019, ten years after her death, multiple tributes poured in to remember the actress and her contribution to teen culture as a whole. Breckin Meyer was one of those to speak out.

Meyer knew Murphy long before either of them were cast in Clueless, so when they were eventually cast as love interests, it only solidified their best-friend bond.

With that said, Meyer made it clear that their relationship was more akin to siblings than romantic, but that they loved working on-set together.

12. The Clueless team have reunited on other projects over the years

The cast of Clueless made no secret of the fact that they loved working together, and that they would continue to work together whenever they got the chance.

These team-ups have been numerous, but most famous is the collaboration between Silverstone and Clueless director Heckerling on Vamps – a comedy about two vampires who are struggling with their love lives.

There was also a Clueless reunion on the sitcom Suburgatory, with Alicia Silverstone starring on a multi-episode arc and Clueless director Amy Heckerling helming one of the episodes.

Not only that, but Jeremy Sisto (Clueless’ Elton) co-starred in the series, giving him the chance to play off both Heckerling and Silverstone.

Unfortunately, neither Vamps nor the TV collaborations were ultra-successful, even if everyone no doubt had a lot of fun on set.

11. A remake is in the works

The immediate success of Clueless meant that it spawned a spin-off TV sitcom as well as a series of novels and comic books.

Not only that, but Paramount Studios recently announced that they have started production on a feature film remake.

The Clueless television show, which ran from 1996 to 1999, didn’t exactly follow the plot of the movie, instead asking the question of what happens when the Queen of High School vanishes.

In the first episode, Cher disappears, and it follows Dionne’s attempts to step into her high heels and run the hallways.

All the same characters are present, only with a slightly more modernised aesthetic, and updated slang terms.

10. The “suck and blow game” is actually harder than it looks

Every teen movie has to have a house party scene – it’s one of the genre’s key recurring motifs – and Clueless is no exception.

Clueless’ own party scene is made even more epic by the fact that the movie is set in Beverly Hills, where every character essentially has their own mansion to run around.

This makes the party a huge and raucous affair, including everything from underage drinking to getting high, and culminating in a game of suck and blow.

The suck and blow game might seem spontaneous and sexy, but the reality of shooting it was far less glamourous.

The game proved way harder to achieve than anyone expected, and so a real credit card had to be swapped out with a cardboard prop.

When that didn’t fix things, the cast were forced to smother their lips in chapstick to make sure the card would stick. Yum.

9. Clueless’ jokes lost the movie an endorsement

All teen movies are a little bit risque – that’s why they’re so popular with an age group that’s constantly looking to feel cool and independent.

With that said, Clueless specifically definitely doesn’t shy away from pushing boundaries, which resulted in the film losing both an endorsement and a shooting location.

Essentially, all of the movie’s restaurant scenes were supposed to be filmed at California Pizza Kitchen, until the CEO actually came to set and looked at what was being filmed.

The plethora of dirty jokes comparing breadsticks to certain kinds of human anatomy allegedly offended the CEO so badly that he refused to allow any scenes to be filmed at his restaurant chain.

Instead, the scenes were changed to take place on school premises – that’s why there are so many scenes set at the high school cafeteria.

8. Paul Rudd didn’t realise Murray was black

Paul Rudd was eventually cast in Clueless as Josh, Cher’s brainy nihilist step-brother and eventual love interest.

However, that was far from the only part Rudd auditioned for. Rudd first tried to play the part of Christian, excited by the opportunity to play a gay character that went beyond just stereotypes into having a real personality and depth.

When that didn’t pan out, he asked to audition for Murray, a character that obviously wasn’t offered to him as an option.

Murray eventually went to Donald Faison, and the character was supposed to be played by a black actor right from the beginning.

Rudd hadn’t noticed this, because reading the script Rudd thought the character was more like a comedic hip-hop wannabe who was trying too hard, not an actual African American character.

7. Heckerling and the casting director wanted two different actresses for Cher, not realising they were both Alicia Silverstone

Looking back, Alicia Silverstone is the perfect casting for Cher, and it’s hard to imagine anybody else in the iconic role.

With that said, Silverstone was a gamble at the time, since not only had she done very little film work, but she was also new to the entertainment industry as a whole.

She was mainly known for her work modelling, and for her work as a villainous schoolgirl in The Crush, where she attempts to murder the older men who she develops crushes on.

Clueless was mainly picked by the director herself and the casting director, who both wanted different actresses for the part.

The director wanted the beautiful girl from the Aerosmith videos, while the casting director wanted the intriguing actress from The Crush.

When they discovered she was one and the same, it seemed like destiny itself was saying Silverstone was perfect for the part.

6. Silverstone really didn’t know how to pronounce Haitians

Though Cher is supposed to be resourceful, cunning and kind, not all of her qualities are positive.

She does have a dumb blonde streak which leads her to be overconfident or reckless, just like when she drives straight past a stop sign without even trying to slow down.

Another example of this not-so-smart side of Cher is revealed in debate class, where she pronounces Haitians as Hate-I-Ans.

This might seem like a classic gag written by the film’s writer, but it was actually Silverstone’s own mistake.

She mispronounced the work after only seeing it in the script and never hearing it aloud, and the director stopped other people from correcting her because the moment was “so totally Cher”.

5. Brittany Murphy was very similar to her character

All of the cast of Clueless were very much at the beginning of their careers when the movie was shooting, and so they were far from living the glamourous life depicted on-screen.

This meant that none of the cast were very much like their characters, with the exception of Brittany Murphy, who played Tai.

Throughout the movie, Tai is portrayed as an uncool person, who doesn’t have great fashion sense and doesn’t really know how to be popular.

She later insults the queen bee of the school when she gets a handle on popularity and ascends the high school totem pole, calling Cher a virgin who can’t drive.

In truth, it was Murphy herself who couldn’t drive, and who had never had a serious boyfriend at the time of shooting the movie.

4. There are several hints to Christian’s identity

One of the biggest themes in Clueless is that very few characters are exactly what they seem to be.

For example, Cher is a rich girl who doesn’t have her life together in the way she wants people to believe she does.

One of the biggest ways in which this manifests, however, is in the character of Christian, whose complete disinterest Cher remains oblivious to.

Despite Cher being unable to see that Christian is definitely more interested in guys than girls, the movie does drop several hints.

Christian suggests movies like Some Like It Hot and Spartacus, and he reads Junkie, by iconic gay writer William S. Burroughs.

3. There’s already been a Clueless TV series

The revived interest in Clueless, from brand new films in the works, to runway fashion and music videos, might distract from the fact that there’s already been a Clueless television show before.

It aired in 1996, and though it did not star Alicia Silverstone, many of the original cast did return to reprise their roles.

The role of Cher was taken up by Rachel Blanchard, who had previously starred in several episodes of Are You Afraid of the Dark and War of the Worlds.

Stacey Dash returned to play the role of Dionne, and Murray continued to be played by Donald Faison across the three seasons.

The show ran from 1996 to 1999, and had a pretty dedicated following, even if it isn’t looked back on super fondly today.

2. Cher has 60 outfit changes through the course of the movie

There are quite a lot of things about Clueless that have become iconic over the years, but the biggest thing is definitely the fashion.

Cher’s iconic yellow plaid outfit has been pastiched and parodied constantly, including in music videos and runway fashion.

Clueless really leaned into the fashion, by giving Cher alone 60 outfit changes across the whole runtime of the movie.

In addition to this, there were 53 different plaid colours and patterns, with different widths and fabrics, throughout the wardrobes of every character.

The result is that almost every scene of Clueless features at least one iconic outfit (as well as a couple that haven’t aged so well).

1. Clueless is actually the second part in a trilogy

Extended universes are all the rage when it comes to superhero movies, but less common with chick flicks and teen movies.

With that said, Clueless is actually the middle instalment of a trilogy of spiritual sequels, which begins with Fast Times at Ridgemont High.

Fast Times, Clueless, and the last instalment, 2000’s Loser, were all directed by Heckerling, who had a passion for movies centring around teenagers and high school.

Each comedy was supposed to draw attention to a different kind of teen outlook, aesthetic and subculture, even if some were more popular than others.

Clueless in particular has remained the most iconic of the bunch, with Fast Times at Ridgemont High coming a close second.

As for Loser, it turns out that the realities of teen life on the cusp of the 2000s is just less engaging for audiences, at least with Heckerling directing.