When Clueless director Amy Heckerling was casting the movie back in the early 90s, she came across a number of up-and-coming actors and actresses who are now household names. In an interview with Vanity Fair for the 20th anniversary, Amy revealed the shortlist for Cher, which included young talents like Cybill’s daughter Alicia Witt, Kelly Kapowski aka Tiffani Thiessen, #HairGoals Keri Russell, and the actress Amy recalls the casting director told her she ‘had to see the girl in Flesh and Bone’, who turned out to be Gwyneth Paltrow.
But the one person that could’ve donned the Alaia dress is Legally Blonde herself, Reese Witherspoon.
“I had my heart set on Alicia… But Fox … wanted me to explore all the options… I met with Reese because everyone said, ‘This girl is amazing. She’s going to be huge.’ I saw some movie where she had a southern accent. Maybe it was on TV, a movie of the week. But I did see some scenes of hers and went: ‘Wow. She’s amazing.’ But Alicia is Cher.”
As for Cher’s love interest Josh, Fox casting director Carrie Frazier was really gung ho on a young Ben Affleck, and was “heartbroken” when he wasn’t cast. Other tidbits – Dave Chappelle could’ve been Murray (Donald Faison) and Sarah Michelle Gellar had to turn down the part of Amber due to her obligation to All My Children at the time.
With the infinite amount of permutations that could’ve happened with casting back then, we could’ve seen an entirely different Clueless – but we think they got it right. But moving forward in an era where there seems to be an announcement for a reboot of some 90s TV show or movie every day (hi, Fuller House, The X-Files, and Twin Peaks), we got to thinking what it would be like if Clueless, which is itself loosely based on Jane Austen’s Emma, what would a modern day BevHills Clueless look like with some of today’s hottest and up-and coming actors? Here are our personal picks for Clueless 2.0 – do you agree?
Kiernan Shipka as Cher Horowitz
What Alicia Silverstone was in 1995, Kiernan Shipka is in 2015. A likable blonde teen who looks impossibly polished, but can still pull off the Girl Next Door thing. Plus if you watched Mad Men, you know that Kiernan is such an incredible actress that she would bring out whole new layers in the character.
Besides, when you think about it, Cher Horowitz is the logical extension of a 16-year-old Sally Draper.
Alternate casting: Amandla Stenberg
Zendaya as Dionne Davenport
In real life, Zendaya is a smart, well-spoken, fashionista. Some of the characters she’s played have a bit of sass, and Dionne is kind of a mix between the two Zendayas. Dionne is also a girl who knows who she is and comes across as super confident, without being arrogant, and that’s Zendaya to a T.
Alternate casting: Maia Mitchell
Rowan Blanchard as Tai Frasier
You’re going to need to bear with me on this one. Do you watch Girl Meets World? No, because you’re a grownup? Fine. Maybe you watched Boy Meets World. Rowan plays Cory’s daughter, and she’s the perfect 2015 answer to Cory Matthews. A little awkward, sort of wide-eyed and naive, but above all a smart kid with a heart of gold. Another 90s character that shared those traits: Tai Frasier. She’s a bit younger than the rest of the prospective cast, but so was Brittany Murphy. It made it all the more believable that she was the fish out of (New Jersey) water.
Alternate casting: Maisie Williams
Dylan O’Brien as Josh Lucas
TBH, Paul Rudd could just reprise his role as Josh because THE MAN HAS NEVER AGED. In 20 years, the son of a gun looks exactly the same. But I guess it would be weird if he romanced a teen Kiernan Shipka. I don’t watch Teen Wolf. Nor have I seen The Maze Runner. But I know a good looking teen idol when I see one. Dylan is one of those folks who is part of multiple fandoms and is big on the Internetz (like the Tumblrs and whatnot). He can be charming and romantic and perfect as Josh.
Alternate casting: Gregg Sulkin
Through Friday Night Lights, Parenthood, and Fruitvale Station, we became Michael B. Jordan superfans. To the point where we will cast him in Clueless although his teen years are long past. I mean, having at least one actor in his or her late 20s is a teen movie tradition, right? While we usually see him in dramatic roles, we’d give anything to see the former Vince Howard explain that he shaved his head “cause I’m keeping it real!”
Only problem: somehow, in some way, he’d manage to make us cry. He always does.
Alternate casting: Tyler James Williams (He’s funny. And he grew up!)
Jaden Smith as Elton Tiscia
First of all, Elton has a last name, apparently?
Second, I feel about Jaden Smith the same way you would about a little brother or cousin. I’m sure he’s overall a good kid who will turn into a great grown up, but Lord, do you want to punch him sometimes.
Punchability, I would argue, is the hallmark of Elton Tiscia.
Plus, not that I doubt Jaden’s acting skills, but it wouldn’t be a stretch for him to play a rich kid who’s so used to getting what he wants that he can’t even imagine that Cher isn’t into him.
Bella Thorne as Amber Mariens
It’s not just the red hair. Bella is just so awesome at playing the girl you love to hate, but she could also bring out the genuine wackiness that is Ambular. But even with atrocious hair and outfits, it’s clear that she belongs in Cher’s tier.
Alternate casting: Mae Whitman
Miles Heizer as Travis Birkenstock
Not to typecast, but did you watch Parenthood? Miles is amazing as a sensitive, lovable stoner. I feel like the 90s teen pothead stereotype (Birkenstocks, ponchos) is a bit of a thing of the past. Now Travis would be a more mainstream skater who made up for in heart what he lacked in motivation.
Christian needs to be handsome in an old-school way, the kind of debonaire gent that never courts ladies anymore … you know, because he’s not into them. Ezra Miller seems like a natural choice for lovable Rat Pack wannabe Christian. He’s so pretty a teen girl would swoon over him, but with the same “I don’t care” attitude that makes Cher think he’s playing it cool and taking their relationship slow. Really, really slow.
Alternate casting: Ross Lynch, Asa Butterfield
They didn’t really give Summer much to do, did they? That makes it the perfect role for a bit of stunt casting. The only requirement: that she be traditionally pretty enough that she makes sense in the Noxzema ad that is Cher’s circle of friends. Our pick is Oscar nominee Hailee Steinfeld, a fantastic actress who could maybe hopefully get a few lines this time around. After Pitch Perfect 2, we’d also like to request a song or two.
Alternate Casting: Ariel Winter, Cara Delevingne
Bob Odenkirk as Mr. Horowitz
My problem with Dan Hedaya as the OG Mr. Horowitz was that he made me think he had a secret life as a gangster – like Al Capone gangster – in the past. I feel like Cher’s dad of course needs to be stern and strict to a certain point, but also obviously caring for his daughter. Bob Odenkirk, while playing a scummy lawyer on Breaking Bad and Better Call Saul, has a heart to him that can take that gangster feel away. He’s also obviously very funny without even trying, so saying just one line in the dryest of tones will make him a stand out star.
Alternate Casting: Jeff Daniels, Michael Keaton
Leslie Jones as Ms. Stoeger
I love Leslie Jones. If you’re not familiar with her work, you probably don’t watch Saturday Night Live. But get to know her because she’s going to be huge. She’s been in the comedy game for a long time, but didn’t become a more recognised name until she was promoted from writer to cast member on SNL. She’s in the new Ghostbusters movie alongside Kristen Wiig, Melissa McCarthy and Kate McKinnon, so you know if you are in their squad, you have to be able to be just as funny, if not funnier. The role of the Ms. Stoger the gym teacher may be small, but in this fake reboot, it could have potential to be big.
Zach Galifianakis as Mr. Hall and Kristen Wiig as Miss Geist
I would like to say for the record that prior to choosing these two, I totally forgot they have a movie coming out later this year called Masterminds in which they play a couple of dumb criminals. Maybe it was in my subconscious, but let’s just face the facts here – I’m a casting genius. Anyways, 20 years ago, Miss Geist and Mr. Hall were 40ish and 50ish in real life, but as a nine year old, they looked so old to me. In our reboot, I think the way to go is to play up the comedy. If we have a cast of teens who are good at comedy, we need adults like Leslie Jones and Bob Odenkirk to knock it out of the freaking park with jokes. The pairing of Kristen and Zach just makes me laugh looking at them and thinking of what could possibly come out of their mouths when paired up together. Kristen also plays shy well, and Zach can play shy confidence. It’s a match made in blog fake movie heaven.