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Time travel may not yet be possible, but for the next best thing watch Clueless. In the two decades since its release, Amy Heckerling’s cult-classic teen movie has become shorthand for Nineties pop culture: flip phones, plaid skirts, sassy slang. The two syllables of its title seem to pack more nostalgia than literal rose-tinted glasses. At the centre of it all is, of course, Alicia Silverstone’s blonde, sweet-as-pie high schooler Cher, a Beverly Hills update on Jane Austen’s most likeably unlikeable heroine Emma.
Now 30 years after the film’s release, Clueless the Musical has arrived in the West End, with original music by Noughties guitar queen KT Tunstall. No one is happier about this than Heckerling herself, who has written a new script, and who from the start had always pictured her candy-coloured story set to snazzy choreography.
“It’s not a realistic world I was making,” Heckerling explains in between rehearsals at Trafalgar Theatre. “It’s happier, nicer, cleaner, richer, with less strife, less racial tension. Everything is wonderful and the only thing to worry about is who likes who.” In short, it’s a musical sort of world. But back then, she shrugs, Hollywood wasn’t making musicals.
Fans of the original can breathe a sigh of relief knowing that this is a faithful adaptation. The story remains the same: teen queen Cher (now played by the equally blonde Emma Flynn) rules her school as a benevolent dictator whose vow to do more “good deeds” leads to her taking a new girl under her wing and playing cupid with two lonely teachers. It remains as compulsively quotable as ever; “As if!” gets a whole song of its own while.
Heckerling’s personal favourite quote? A line delivered by Cher during a class debate about Haitians seeking refuge in the US: “May I please remind you; it does not say RSVP on the Statue of Liberty!” Heckerling pauses, adding dryly: “Although it probably does now.”
Picture the creator of Clueless. Now picture the opposite, and you’ve got someone close to Heckerling. The writer, now 70, wears black skinny jeans and a black jumper. Her black hair is unruly, forming a fuzzy halo knotted around her head. And her black eyeliner is heavy. Far from any leisurely Valley Girl uptalk, Heckerling speaks low and fast in a Bronx accent. A real New Yawker. All of which to say, she is the antithesis of Cher, which was, of course, the whole point.
When I met Alicia Silverstone, I just loved her. She did this goofy thing, where instead of picking up her glass of soda to drink, she put her head down to the glass like a little kid
Heckerling first read Austen’s Emma as a film student at NYU drowning in Kafka, the Russians, and Dickens (“not even his fun ones”). Years later, after she had established herself in Hollywood writing films including Fast Times at Ridgemont High and Look Who’s Talking, she was brainstorming what to do next when a question came to mind: what would the world look like if life was easy? If Heckerling was the type of person everyone instantly loved, the sort of woman who looked great in every outfit and didn’t have cares in the world? “Who in culture is like that?” Heckerling asked herself. Emma! And Cher was born – brought to life by Silverstone who was 18 and a relative unknown at the time.
Heckerling set up a meeting with Silverstone after seeing her play a teen girl breaking bad in an Aerosmith music video. “It was just something about her,” says Heckerling. “I felt this warmth. And then when I met her, I just loved her. She did this goofy thing, where instead of picking up her glass of soda to drink, she put her head down to the glass like a little kid. There was something so innocent and childish about her.” Down the line, there was talk of Gwyneth Paltrow and Reese Witherspoon being cast, but Silverstone and her soda niggled in the back of Heckerling’s mind. Finally, she submitted the script to Paramount with a VHS tape of Silverstone’s Aerosmith video attached.
The film opened at number two at the US box office – a surefire hit for its creator and stars. More important than its cash haul, though, are the years that followed, which have seen Clueless venerated to cult-classic status. Its success spawned a TV show, written by Heckerling and starring Peep Show actor Rachel Blanchard, and a 21-book series. As recently as 2020, there were talks of a Veronica Mars-style spin-off that would focus on Cher’s equally chic BFF Dionne (Stacey Dash).
Granted this isn’t even the first time that Clueless has got the musical treatment. In 2018, Disney alum Dove Cameron stepped into Cher’s Calvin Klein LBD for an off-Broadway jukebox musical that remixed Nineties songs (think Aqua’s “Barbie Girl” rejigged as “Valley Girl”). This time around, singer-songwriter KT Tunstall and lyricist Glenn Slater (School of Rock; Sister Act) penned original numbers all shot through with the Nineties MTV energy of the original soundtrack. “Human Barbies”, for example, a song about Cher’s ability to manipulate and charm those around her, is a Green Day-style pop punk thrasher.
On why Heckerling chose to do away with the jukebox format, she points to a “negative vibe” around jukebox musicals right now – an acknowledgement perhaps to the show’s less-than-favourable reviews.
Even before 2018, Clueless the Musical was decades in the making. It was first workshopped by producing legends Barry and Fran Weissler (Chicago and Pippin) but things didn’t click, says Heckerling. They wanted different things; the Weissler version would’ve shifted perspective onto the housekeepers and gardeners of Beverly Hills, filtering Cher’s story through the eyes of hired help: Clueless as social commentary. It didn’t make any sense to Heckerling. This was her perfect bubble of sunny optimism and the Weisslers wanted to burst it.
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“It’s a movie,” she says. “Movies are fantasies that make you feel happier, stronger, bigger. You don’t watch Peter Pan and say, ‘Hey, most guys don’t wear tights and fly around.’ Or Fred Astaire movies, they’ll be in a room with shiny floors. In the Bronx, there are no shiny floors, trust me, but I want to see it on screen. I want to pretend to live in it.”
The world could do with a little more escapism, according to Heckerling. Or a lot more. Take this year’s Oscar nominees. “I watched most of the films and I was just like, ‘This isn’t making me any happier,’” she says. Heckerling had hoped Best Picture winner Anora would end happily, in a “they rode off into the sunset” sort of way. It did not.
For those of a certain age, Clueless is a generational touchstone – single-handedly responsible for popularising plaid outside of Scotland and introducing “whatever” into the cultural lexicon. For others, including Chyna-Rose Frederick, the actor playing Cher’s BFF Dionne, this musical will be their introduction. “I hadn’t watched the film until I auditioned, which is probably sacrilege,” laughs Frederick. That said, she was still familiar with the characters thanks to the film’s chokehold on Halloween costumes. “And I knew Dionne and [her boyfriend] Murray as the glamorous young Black characters of the Nineties. I always looked up to them.”
There is no escaping the fact that most of the actors in Clueless the Musical were not born when Heckerling’s films hit cinemas – and wouldn’t be born for quite some time after. But while they may have no clue what a flip phone is, they understand its place in the pantheon of great romcoms – not least Flynn, who is taking a “purist” approach to playing Cher.
“I know that if I was coming to see the musical, I’d want to see the parts of the film that I loved so much,” she says. Flynn – who previously played Legally Blonde’s Elle Woods on Broadway, the other iconic romcom blonde – worked hard to mimic Silverstone’s speech, the way her mouth moves and her cadence. “It’s part of the reason why people love Cher so much.”
Heckerling knows it’s a tall order for the musical to live up to the film, particularly for fans of the original, but she is excited, nonetheless. Amid news that Paramount has ordered a reboot of Clueless without so much as a cursory email to let her know (“It’s like, well pay me because I created the characters!”) Heckerling takes solace in the fact that this musical is hers.
Before we part ways, I’m curious to know what Heckerling thinks of the small asterisk that has attached itself to the vaguely incestual love story at the heart of Clueless between Cher and her ex-stepbrother Josh. Heckerling doesn’t understand. “First of all, my grandparents are stepbrother and stepsister. I mean it’s the ghetto, you’re not swiping on your phone. It was whoever was around.”
Letting a minor familial technicality stop a love story for the ages? As if!
‘Clueless the Musical’ plays at London’s Trafalgar Theatre until 27 September 2025. Tickets from cluelessonstage.com
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