Teen movies were thought to have had their day by the Nineties. John Hughes had appeased adolescents and critics in equal measure with his studies of suburban growing pains in the Eighties, but few films managed to conjure the same drama and hi-jinks from school corridors by the early Nineties. Studios were sick of hearing pitches about the nerds and the outcasts from male writers.

Something fun and fresh was needed - and Amy Heckerling, the tousle-haired creator of Fast Times at Ridgemont High, had something that fit the bill: Clueless.

Inspired by a combination of Jane Austen’s Emma and the antics of Sixties surfing TV series Gidget, Heckerling took the glossy citizens of Beverly Hills and planted them in a unique, hyper-real pop culture-infused world. The end result was teenagers who, in the words of New Kid Tai, “talk like grown-ups”. Love, lust, matchmaking and shopping collide around Cher, an effervescently optimistic daughter of a single-father lawyer, who just wants to make the world a better place.

Initially, Clueless fell foul of the same prejudice that Hollywood is churning over even now: it was dropped by Fox, the first studio to own rights to the script, for being too female-orientated.

Paramount took it on instead. With a pared-down budget of just $12 million, a young cast of Hollywood hopefuls and Heckerling’s innovative approach to youth culture, Clueless was launched in the same summer as Disney animation Pochahontas and space tragedy Apollo 13.

The studio gave it a good push: there were promotional fluffy pens and guides to ‘Valspeak’, the slang perfected by privileged Californian teens, and MTV, the studio’s sister company, trailered it heavily alongside the Aerosmith videos that landed Alicia Silverstone the starring role.

It went on to become the summer sleeper hit, eventually grossing $55 million during its run in cinemas. But Clueless’ cultural impact was far greater: costume designer Mona May’s outlandish designs dragged America’s teens out of a hangover of Nirvana-tinged grunge, Heckerling’s script provided quips that would be quoted by teenagers worldwide, Brittany Murphy’s untimely death nine years later was felt all the stronger because of her sweet portrayal of Tai, the character who inspired the film’s title.

Two decades on, a third generation are being introduced to Clueless - most recently by rapper Iggy Azalea’s direct homage to the film in her video for Fancy. It’s now a bona fidel classic, one that shook up the teen movie genre as much as it did female-focussed comedies. Here’s how it was made.

THE BEGINNING

"Dionne and I were both named after famous singers of the past, who now do infomercials" - Cher

Amy Heckerling and Twink Caplan had been working together for some years by the time Clueless came into being. After meeting in the mid-Eighties at Universal Studios, Heckerling took then-actress Caplan on as a secretary. A decade later, when the idea for Clueless first came to Heckerling, Caplan was working as her associate producer.

Alicia Silverstone as Cher on the set of Clueless Credit: Rex Features/Moviestore/REX Shutterstock



AMY HECKERLING, writer and director: I was asked by Fox’s TV department to pitch them an idea. They said, “we want you to do something about young people. About the cool kids in high school, because all the guys pitch us high school ideas always pitch them about the nerds.”

I had always been interested in a character who is extremely optimistic, and what it would be like to be the kind of person who didn’t have any self-doubt. So I wrote Fox a pilot about this very happy character, Cher, and they didn’t want to do it.

TWINK CAPLAN, associate producer, Miss Geist: I had worked with Amy for five years before Clueless. I went to the library with her for research, everything. We did everything together.

AMY: It was a time in my life when I was unhappy with the way things were going. So I switched agents and one agent, Ken Stobick, said, “This isn’t right for TV - this is a feature.”

TWINK: Amy always wanted it to be like Emma, but a modern-day Emma, who sees the glass half-full instead of half-empty. She was always positive, even when her Dad would yell.

AMY: I remembered in college I read Emma, and I loved it. And it hit me: Emma is dealing with so many of the issues the modern stories on TV do. So many of the things seemed to just nudge slightly into the future it just fitted perfectly.

It was 1995, so Cher was 15 going on 16, she was born in 1980, which meant her mother was a teenager in the late Sixties. She would have looked to the famous women then and thought, "I’m going to have a daughter named Cher”.

When I was writing, Dionne Warwick had a connection to a psychic line and she was representing that, and Cher was associated with some hair products. So there was this idea of classic female singers who were both on TV selling products.

My friend Carrie Frazier is a casting director. I was writing the script when the Aerosmith videos first launched, and Alicia [Silverstone] was known as the Aerosmith girl. She was in three of their videos and I saw her in the first one, and videotaped it so when I handed in the script I could show them the girl that I liked.My friend Carrie kept telling me I had to see this girl, she was in The Crush. Her name was Alicia Silverstone. And I was like, “but I want the Aerosmith Girl!” Ultimately we were talking about the same person.

TWINK: We all knew her from the video, then Amy went for dinner with her and just loved her. When she was sipping her drink through a straw, instead of taking the glass and straw to her face, Alicia leaned over the table to sip the straw from the glass. And Amy thought: “Oh my god, this is my girl." Alicia was Cher, she is just the sweetest girl, she still is.

ALICIA SILVERSTONE, Cher (speaking to the Winnipeg Free Press in 1995): When I read the script, I thought every page was so hysterical. I was actually scared of this girl, because I did grow up in an affluent area and there were girls who were that materialistic.

AMY: I didn’t audition Alicia so much as I met her, I loved her, I knew I wanted her. The studio wanted to see her do a scene, so we did a scene, then we moved it to another studio, and the other studio were fine with her.

THE CAST COMES TOGETHER, AND PARAMOUNT ENTERS THE PICTURE

"Some teachers are trying to low-ball me, Daddy. And I know how you say, 'Never accept a first offer', so I figure these grades are just a jumping off point to start negotiations" - Cher

Heckerling pitched her script with Alicia Silverstone in mind, but before long Fox had pulled out of the project. It would take a mixture of good fortune and production talent to get Clueless - then under a different title - back on the road, and a casting director with a keen eye for young talent to start the careers of Clueless’s cast.

Alicia Silverstone, Brittany Murphy, Stacey Dash in Clueless Credit: Film Stills/Film Stills

DONALD FAISON, Murray: When I first saw the script it was called No Worries 1, but I thought it was No Worries I, which didn’t understand. It was over at Fox, and I auditioned maybe four times for Amy and then it went away. And I remember thinking, “Wow, I had some pretty good auditions for this, I guess I didn’t get it.”

TWINK: 20th Century Fox decided they wanted it to be more about the boys than the girls, and Amy wouldn’t do that, so they just put it into turnaround, and when they put it into turnaround we left.

AMY: (speaking to The Baltimore Sun in 1995): They were worried about something that was so female-oriented. They kept pressuring me to create more of a life for the boys in the film, to create more of an ensemble piece, which didn't make sense to me at all.

SHERRY LANSING, former CEO of Paramount Pictures: I have no knowledge of why Fox dropped it but I love female-orientated movies. For me it seems so silly now, when you see what’s happened in the marketplace, that anyone wouldn’t have recognised it right away.

TWINK: By that point we were working out of Amy’s house. We didn’t even have an office anymore. Then somebody showed the script to Scott Rudin at Paramount, he read it and he loved it and got in touch with Amy.

SCOTT RUDIN, producer (speaking to NPR in 2008): Well it was a fantastic experience. That was a script that was sitting on a shelf at Fox, going absolutely no place. And it was sent to me by Amy Heckerling’s agent, who was trying to get me to hire her to do something else. So I read it, and called Amy Heckerling and said, why can’t we just do this? This is great. It was so fresh you could feel it blow the doors of the hinges.

SHERRY: One of of the lucky things that happened to us was that it was in turnaround. So Scott brought it to us. I can remember getting a call, I was on an aeroplane because you could make them in the air then. It was Scott and he said, there’s his fantastic project I’m sending you, and I want you to read it right away, and we have a chance to pick it up. I read it, and then I called him back and said, “I love it, let’s make it.”

MARCIA ROSS, casting director: Scott Rudin took over as producer at Paramount, and ended up vastly reducing the budget so they could get the movie made. Alicia was the one of the pieces of casting that remained from that time when it was at Fox.

DONALD: It turned up, maybe six months later, at Paramount. And it was called something different, The Clueless Years or something like that.

SCOTT (speaking to NPR): It had an absolutely terrible title at the time. It wasn’t called Clueless, it was called I Was A Teenage Teenager.

DONALD: I didn’t understand the script. I knew it was a high school movie and I was really big into high school movies. I thought if I could do a high school movie I really would have accomplished something.

It was a world I wanted to be a part of. I wanted to do something completely different from how I grew up, and I wanted to do it like they did it in the movies. My character was just this wannabe, which fitted perfectly because I really wanted to be the characters in the movies that I saw growing up.

STACEY DASH, Dionne: I got very excited when I first heard about the audition, because Fast Times at Ridgemont High was one of my favourite films. So I was just beside myself, and then I read the script and thought, I’ve got this. I knew it. I knew it was my role, I just knew it. I walked in basically owning it.



TWINK: Stacey was great. It was very distracting because she was so pretty but she was really fabulous, she really was. She came back a few times. Everybody wanted to do this.

AMY: I saw a lot of girls and Stacey was by far the one I loved and wanted.

STACEY: From the first audition Amy loved me. I’ll never forget when I got the call. I was on Abbot Kinney and Main Street, Santa Monica, crossing the street, and I nearly almost got knocked over by a car because I stopped and I was screaming, I was so happy. That was it, we started shooting.

DONALD: I only had to audition once by the time it had gone to Paramount, and then they flew me out to Los Angeles to test with Stacey and Alicia. Our screen test was the freeway scene. They set up three seats, and we pretended like we were driving down in front of a camera.

It took a while for Stacey to warm up. We had to get used to each other. Once we did there was no problem, but I’m sure I scared her off - my eyes were so big and I was enamoured by her. I remember telling my friends that I was going to be dating the girl from Mo’ Money and they were going crazy, asking if I was going to kiss her. I was like, “Yeah! You bet I’m gonna kiss her. I’m gonna give her a good kiss too!”

I think she could tell that I had a huge crush on her, so maybe she was a bit standoffish because of it.

STACEY: I didn’t know he liked me! That’s so funny. I didn’t know that but I loved him. It was great, because we had the best chemistry, it was there, it wasn’t acting.

TWINK: I know Stacey said she had this audition with Terrence Howard. I was in the room all the time but I didn’t know that was Terrence Howard.

PAUL RUDD, Josh (speaking to Perez Hilton in 2013): It was so exciting because it was one of the first movies I did. I remember being like, 'Oh my God, this is the Paramount lot!' You know, those huge gates. 'And it’s the girl from the Aerosmith video!’

Paul Rudd as Josh and Alicia Silverstone on the set of Clueless Credit: 1995 Rex Features/Everett/REX Shutterstock

MARCIA: I had met Paul when I was casting a television movie, so I brought him in for the second session of auditions and he read for several parts. And we really liked him, but they decided to go with someone else. Paul went and got another job, but the other guy didn’t work out, so we went back to Paul and he was screen tested, and he was amazing. He went through a lot to get that part, many many auditions.

When it came to doing chemistry read-throughs, the minute Alicia and Paul were in the room together, you could see it. You could tell that they were right together.

TWINK: Out of all the roles, the one who was hardest to cast was the beatnik boy. That was the hardest to find.

MARCIA: I remember Christian being a really challenging part to cast, and we’d auditioned so many people and it just wasn’t right. And I remember Justin walking in that room and you could just tell he had it. That was it. We didn’t know who we wanted for Christian until then.

JUSTIN WALKER, Christian: I really clicked with that role. I was in New York, studying Theatre Acting, and when I read that material I just felt it. I was looking at the material and I just was walking up 8th avenue to the Paramount Building and I was like, “I’m getting this”. I just knew it. And there was just a rhythm to it that I identified with and I felt that they felt it was in the room as well.

AMY: Christian was someone who has made a study of the Ratpack, he reflected the resurgence of the swinger mentality in the Nineties. So he brings back jive talk vocabulary.

JUSTIN: I liked the lingo. The way he moved, he just had this kind of cool aesthetic that I identified with. Donald Faison and I were both from New York, so we flew out for the screen test together and we flew back together. I will always think of him as a brother in this whole thing.

I knew then and there that Christian’s sexuality would change many things, for characters moving forward but in particular, for me. The fact is, when that is your first known role, people label you. In my case, I became the gay guy from Clueless.

WALLACE SHAWN, Mr Hall: Amy and I had discussed a previous project a couple of years earlier that never got made. I suppose they thought I was a good casting, I didn’t have to audition. I actually had been a schoolteacher and so I knew some of that from the inside, and at that time, I was an acceptable person to be in a movie.

TWINK: Amy wrote the part of Miss Geist for me, I think she was based on a teacher Amy had back in school and she thought I could portray her. I was producing too, and in the first meeting we went into with Scott, my hair was a mess and I had a pencil in it - we just had to go in really quickly one day. Geist was mentioned, and Amy pointed and said: “there she is.” Unbeknownst to me, being a slob that day was perfect.

Brittany Murphy as Tai in Clueless Credit: Rex Features/Everett/REX Shutterstock

MARCIA: Tai was one of the harder roles to cast, too. Brittany came the the audition with her mother, and she was so talented - but I don’t think she knew how talented to was. She was the most sweet-natured, self-effacing thing.



TWINK: You know, Brittany was undiscovered talent. We loved her so much we let her sit in the room while a few other people auditioned. She was sitting on the floor next to me, she was so cute, little Brittany. That laugh! She was always laughing, after everything she said she had that little laugh.

She was very close to Sharon, her mother, if we’d have a party or anything, she’d always ask if she could bring Sharon. They were devoted to each other.

MONA MAY, costume designer: She was only 17, she brought her mom onto the set and she was really great, she was very mobile in a sense. I think she was really one of the great promising actresses of the age. She just really knew how to how to go very far in the direction of the young girl who comes in and is a little dumb. It was fun working with her.

AMY: That’s the one sad note in this whole thing. She was very young. I don’t know if it was Hollywood, or what was going on in her life. She had a very loving mother, but she was a young girl so naturally there was all sorts of boyfriend issues. The industry is hard on people. I don’t know exactly why and what happened, but I know that there’s no reason why she shouldn’t still be here celebrating with us. She was just such a sweet, energetic, wonderful spirit.

THE FASHION

"Where’s my white collarless shirt from Fred Segal? It’s my most capable looking outfit!" - Cher

“I only wish I had done a tie-in,'' said Bloomingdale's senior vice president Kal Ruttenstein after seeing the film. “It'll be required viewing for our juniors buyers.'' Ever since Heckerling had imagined Clueless, clothes came hand-in-hand. Hundreds of costume changes, literal tonnes of garments and a tight budget birthed a wardrobe born of creative necessity - which would go on to change youth fashion forever.

Mona May's designs for Cher and Dionne in Clueless Credit: Mona May/Mona May

MONA: I worked with Amy Heckerling prior to Clueless on a pilot and we absolutely fell in love with each other. Our artistic sensibilities are very similar. When she got Clueless, she just called me and said, “you’re the girl”.

LEESA EVANS, assistant costume designer: I’d known Mona for a little while and she knew that I had a fashion background, so she asked if I could come and help design the women’s clothes.

MONA: Amy loved fashion. We would send each other pictures from magazines and were constantly talking. We’d make mood boards to deeply understand how each girl’s style is different. It was very important that each girl’s style really supported the character.

Amy wanted Clueless to be different. When the movie was made, there wasn’t a lot of high fashion. Grunge was in. We went to high schools all over LA to do scouting, and everyone wearing ripped jeans and baggy clothes.

I think the groundbreaking thing was how Clueless changed the way girls dressed. The movie came out and flipped the nation in a sense, every girl had to wear the over-the-knee stockings.

Dionne (Stacey Dash) and Cher (Alicia Silverstone) in the plaid suits and knee-high socks they became known for in Clueless

BRITTANY MURPHY, Tai, speaking in cast interviews, 2006: I really attributed to Amy having a finger on the pulse of what’s going on, what’s now, what do kids like, what are teenagers into.

LEESA: All of a sudden Clueless hit and it was a throwback to this more formal way of dressing, of matching bags and shoes and hats - things that people hadn’t done in a little while. It was refreshing at the time.

MONA: Cher was very feminine and pretty, almost OCD-levels of perfect. Dionne was much more funky, a little sexier. Her skirts were tighter, her textures were more interesting - vinyl and leopard and brighter colours. Then there was the fashion victim, Amber, she was really over the top with ensembles: she’d go for the sailor look or the Pippi Longstocking look, they were all very distinct.

ELISA DONOVAN, Amber: What I remember the most is having such a ball with Mona and Leesa. I would go into that room and they would pull out these absurd things. There was always a theme - like, the sailor outfit or the camouflage outfit, whatever insanity it was, Amber would take it off the runway and wear it to math class.

STACEY: The hats! That was Dionne’s thing, she loved the hats. My favourite outfit is the first one, with the hat that looks like a pretty little cake.

MONA: Alicia was so young and she was just so innocent, she was very preppy. She had about 60 changes in the film, so we had to have masses of fittings, and during those we taught her how to wear the clothes, how to walk a certain way when you are wearing these type of clothes.

ALICIA, speaking to the Allentown Morning Call in 1995: I had to do a lot of research for this role because I hate putting nice clothes on. I like to wear black sweats and a T-shirt. I'm down-to-earth, a total tomboy.

LEESA: Alicia was naturally inquisitive. She would always ask me: “Well, why does this look good? Why do these pieces go together like this?”

It was always fun to go into fittings because we would get into conversations about why Cher would wear certain outfits, how someone’s style dictates their fashion. We took something so simple but so effective: everything Cher had matched, to the point that that it didn’t surprise you that she had a grander scheme of how things should work, of who should be together, because you just saw that she was just a girl who had it all figured out.

MONA: For 60 changes you have to bring tonnes of clothes, that tends to happen over several weeks, and you have to find the same consistency of character for each person.

Stacey Dash, Elisa Donovan, Alicia Silverstone in Clueless Credit: Rex Features/Moviestore/REX Shutterstock

STACEY: There were just racks and racks of clothes. We did a fittings for a whole week, that is so rare for a film. Usually you do two days, and we did seven, 10 hours a day of fitting. That’s how many clothes we went through, racks and racks and racks. Then Amy just designed things specifically for us, too.

MONA: When Alicia put on that yellow suit, it was like, “Oh my god. Here it is: this little girl who rules the high school, who dresses perfectly, and has this little ensemble that nobody had ever seen before. Wow, here she is.”

MAKING FRIENDS ON SET

"This is where Dionne lives. She's my friend because we both know what it's like for people to be jealous of us" - Cher



For 40 days over the winter of 1994, the Clueless cast and crew descended on Occidental College in Los Angeles as Westfield Fashion Square in Sherman Oaks to film their movie. For many involved, it was their debut movie experience. A heady mix of a young cast, Heckerling’s nurturing directorial approach and the optimistic feeling of boundless positivity made for the irrepressible energy that comes through on screen.

WALLACE: Making the film felt like going to a rather innocent party where one of the games was, “Let’s Make a Movie”. The cast were not necessarily people who even were planning to have careers, they were just doing something in itself that was entertaining and amusing and fun. It was totally delightful.

AMY: It was probably the happiest experience I’ve ever had. Everybody was great, everybody completely understood their characters and brought a lot to it. It was so much fun and they were all wonderful people.

DONALD: It was so laid back. I met Breckin Meyer at the audition, but on set we shared a trailer and we pulled back the divider between the two halves and hung out the whole time. Filming was easy: you show up, you hang out in the trailer, you take a nap, you go shoot a scene.

AMY: Donald and the the boys were always goofing around. They just had a nice chemistry, all of them. It felt like if you left them alone they’d want to be horsing around together.

STACEY: We’d sit together in each other’s trailers and talk and hang out and joke around. It was fun.

ELISA: We had a ball the entire time, it was kind of a dream. You’re going to work with all people your own age, you’re wearing crazy costumes and it was the beginning really for everybody.

We just laughed all the time. We were exhausted too - especially Alicia, I mean her schedule was just insane. But it was great, we had a terrific time.

BRECKIN MEYER, Travis (speaking to the Winnipeg Free Press in 1995): I admit that I was expecting to have 'the Aerosmith girl' come in with her entourage of bodyguards, wink at me and make me melt. But she was so sweet and so real, it just made me go, 'Wow! She must be a good actress, because she's nothing like the Aerosmith girl.'

JEREMY SISTO, Elton (speaking to People in 2015): I did a movie with Alicia right before, and we kind of had a crush on each other. It was very sweet.

JUSTIN: To get a movie out like that, with that kind of humour, you have to get the creative energy of Amy Heckerling as it translates through Alicia. It was very non-pressured. Making a movie - behind the scenes there were constraints with budget and time - but as far as how Amy interacted with us, it could not have been more appreciative and relaxed.

TWINK: Oh, it was wild. The set was crazy. Alicia had this little dog, and it would crap outside the make-up trailer, people were complaining they were stepping in s---. I had to say, “Listen, can I get him a leash or something?!”

Donald was so full of energy and Stacey was so beautiful, each kid was just fantastic in their own way. Adam Schroeder [production assistant], he’d always have food fights. I just be eating and then all of a sudden there’d just be spaghetti all over my neck. Breckin had a huge crush on Amy.

BRECKIN, speaking in cast interviews, 2006: Amy’s not at all what you’d expect. Being a young actor and going and meeting all these directors and stuff, you don’t expect this Japanimation-looking, adorable girl, which Amy is. She had black eyeliner on, really cute Tim Burton hair, and like tights and a black skirt. She was super-cute. It’s rare that you’re really, really attracted to your director.

SHERRY: It was just a totally perfect movie experience that ended up making a classic movie. I don’t remember fighting with Scott, I don’t remember fighting with Amy. I don’t remember saying “oh don’t cast this one, cast that one”. It was just too good to be true.

STACEY: I thought it was adorable how naive Alicia was, all she cared about was her little dog. What was weird was that I was so much older than everyone, and I had a child at home. So my mind was in a different place when they said “cut.”

ALICIA, speaking to AP in 1995: I don't know a lot about sex, because I'm a little girl. But what I do know is that when I was younger and I thought about what I wanted when I grew up, it was going to be romantic and beautiful. And private. And it's none of those things anymore.

AMY, speaking to the Los Angeles Times in 1995: It's shocking. After spending months with Cher as the character, then I see her again, and I realise she's not Cher at all. She's Alicia, a little girl. She's very happy with her dog and wearing sweat pants. And then she'll get all glammed up and go to work.

Amy Heckerling with Alicia Silverstone and Brittany Murphy in Clueless Credit: Twink Caplan

WALLACE: Amy is a very unobtrusive director. She seemed like she was one of the kids in the class, but somehow always came up with something that you wouldn’t have thought of but that you were capable of doing and that was fun to do. It’s kind of the definition of good directing.

MONA: Amy was such a great leader, she really pushed everybody. Actors were acting well, everybody was creating. With the costumes, she’d say: “What the hell, what kind of hat do you have? What else can we add?” That is so rare, directors are usually like, “no, stop, it’s too much.”

BRITTANY, speaking in cast interviews, 2006: She made everyone feel really comfortable, within their atmosphere and character and creating this environment that was so conducive to doing your work in, and not making it feel like work at all.

TWINK: We were filming one of the classroom scenes, and Alicia kept saying “Sporadicus” instead of “Spartacus.” Amy and I are smiling at each other and we kept telling people, “don’t say anything”, because we just wanted it to be authentic. Amy just wanted to do it again and for Alicia to not not know. Because that was the brilliance of the Cher character - she was adorable and young, and Alicia was adorable and young, I don’t think she even knew about Spartacus.

ALICIA (speaking to NBC News in 1995): Well, the title is the one thing that throws me off because I think Cher is a very intelligent character, and the whole film is so intelligent that the title sort of a joke that that they are clueless because the characters are so defined and so well-rounded that they really aren't clueless. But I guess that means without a brain, right?

ELISA: I feel like Amy was responsible for the "Whatever" moment. She’s just a genius like that. She was so clear in her vision but she also just allowed us to blossom in these ways, and create the characters in such a specific and fun way.

People still do it to me, or they’ll send me gifs of it. I hear it on the radio sometimes. It’s quite incredible. At high school I had this crazy relationship and when we would fight my boyfriend would always say to me, “Whatever.” It made me so infuriated, that word made me so angry. And when that became the word of my character in the movie, I thought, this is amazing. So it was kind of a nice divine providence.

AMY: I know that Paul was really good at improvising dialogue and he would also bring a lot to the script. He was very intelligent and was good at creating things that character would say in a funny way.

Donald Faison and Breckin Meyer brought a lot of vocabulary that their particular characters would say, as was Stacey. Someone would say, “Can I call this my blah blah blah” and I would go, yeah, that’s cool, go for it. People were alert and would know exactly what their characters were and what the tone of the piece was.

STACEY: I love the party scene, when another girl is dancing with Murray [Donald Faison], and I pull her by the hair. That was so funny, because I came up with that, I just did it. Amy didn’t say, “Go pull her hair” or anything, she just said, “Okay, he is dancing with this girl…” and I come into the room and that was my response, to pull her hair. I was so mad at him because that’s the kind of relationship we had.

BRECKIN (speaking in 2006): There’s a scene where Travis is giving his bong to the Pismo Beach fund. It’s the moment when he tells Cher he’s in rehab and hands her the bong, and when she suggests it go in kitchenware, I say, “That’s where I used to keep it!”. It was one of those moments where I said to Amy, can I say this? And she said, “yeah, try it”, and we did and it worked.

DONALD: When we were filming that party scene and Jeremy Sisto [Elton] is trying to convince Cher to ride with him and let someone take Brittany’s character home. Jeremy’s shirt got caught in the door in one of the takes and he goes to grab Alicia, but his shirt’s in the door and it pulls him back like a slingshot. I was laughing my ass off at it.

MARCIA: The casting of the guy who holds Cher at gunpoint was a complete accident. The original actor had another role on the day we were meant to be shooting and he cancelled at 1pm. I had to cast another actor by 5pm. Nobody had mobile phones back then, I was literally calling everyone at their office and nobody was picking up. It was only because Jace Alexander was working with Scott at the time that he got the role.

TWINK: Amy had written a scene where Cher wakes up from a dream that Paul Rudd is marrying me. So we shot a scene where Paul and I walk down the aisle. It was really cool, but it went in editing.

Twink Caplan in the wedding dress made for her for Clueless Credit: Twink Caplan/Twink Caplan

For my wedding dress they ordered me a slantboard, those things you sit on because it was too tight to sit down in. Every time I ate something Mona would be right after me shouting, “don’t eat anything!” She was like Hitler!

MONA: It was so cool! She designed the dress with me. Twink had something very specific in her mind, which was to have a high collar, be backless and very fitted with a little bit of a fishtail. The tailor I had used to be an architect, and the dress really looked like an architectural piece. Once we made it, she couldn’t really move, and I was chasing her telling her to not eat things!

AMY: While we were in production and editing I had to do the voiceover, before Alicia filled in, There are some very wacky versions where there’s this pretty young blonde girl with this depressed Jewish woman in her head. So that’s kinda weird.

TWINK (as reported by Entertainment Weekly in 1996): There was a line, said by Cher, who refers to a faded romance as “Gone. Completely gone. Like a Chevy Chase film after one weekend. ”Sherry said: ‘Oh, Amy, he’s a good guy. Please don’t use that’. It was removed.

THE LEGACY

"It’s like that book I read in the 9th grade that said, '‘Tis a far, far better thing doing stuff for other people' - Cher

Twenty years on, a third generation is discovering Clueless. The clothes, music, actors and, perhaps most significantly, script, live on in pop culture, cementing the film’s contribution to the cinematic canon. Here’s how the cast felt when they first saw the film, and what impact they imagined it would have.

ELISA: We went to a test screening in the spring, and it was Alicia, Donald, Justin, myself and Paul. I sat next to Alicia, in the back row, with a full audience of people. And from the first moment I looked at Alicia and said, “you’re going to be very famous, very soon.”

And you could just tell. Test screenings are really telling because people have nothing - they haven’t heard anything about the movie, and nobody knew who any of us were. It was a very good litmus test of how people are going to respond. And the reaction was so strong and so positive, and I just went, “wow, this is going to be something.”

DONALD (in 2006): First time I saw it I was with Alicia, I was with Breckin and Paul Rudd. To see how the audience reacted was amazing. I remember coming out and everyone was saying, “You were great! I sucked. But you were great!”. I was like, so that’s how it works out here. Yeah, I sucked too!

JUSTIN ( in 2006): All I could do was look at my hair, and my hair said, ‘fool’. I hated myself on camera for the most part. I just couldn’t deal with it - my voice, my ‘do, my movements. Aside from that, I knew how good it was.

TWINK: I remember the day we were going to show it to Sherry Lansing. It was very quiet in the audience and I was sitting next to Amy, and Sherry was sat right behind me. She laughed through the whole movie. She has this wonderful laugh, a fabulous laugh, Amy and I kept kicking each other and stuff. We just felt so great.

SHERRY: Twink is absolutely right. I thought the movie was hysterically funny. I’m sure I had almost no notes. I also thought it was very touching. I just loved it. I’m not an easy laugh; you look at a movie and you’re constantly trying to make it better. But every once in a while, you see a movie, and the notepad you have is blank - and you just say, “This is genius.”

MONA: When that movie came out, it felt like people, especially the young women, were ready for this message that you can be feminine, you can be a girl, you can be sweet and bitchy. There weren’t girl movies before that. That was the first one. It really was so innovative at the time. I’m just proud to be part of that, I always loved it, I played with those fuzzy pens. It in some ways defines me as a designer.

STACEY: I watched it for the first time with my daughter about a year ago, when she turned 10. I loved it. But I loved myself in that film, and I feel so proud of myself in it. I feel so proud to be part of this iconic film and to have a daughter - it means even more now.

I remembered every single thing. Although going into the teachers’ office and putting the note into the cubby hole, I’d forgotten about that. Watching myself say my favourite line, “There goes your social life”, that was awesome.

ALICIA (speaking to Queen Latifah in 2014): When I was shooting the movie I never had any idea that it would be a cultural phenomenon, I didn’t even know if anyone would see it. I was just doing a role that I really loved and it was quite overwhelming and really surprising that so much had happened.

BRITTANY (speaking in cast interviews, 2006): Amy just made this brilliant pop culture iconoclastic film and I had no idea that that was what it was to be.

DONALD: I don’t think anybody knew we were making Clueless - what it was, what it turned out to be. I think we thought we were making a silly high school movie, and the ones who had the vision were Scott Rudin and Amy Heckerling and Twink Caplan. They knew.

TWINK: I knew at the time, yep. Yeah. I knew it would be huge because I remember saying to Amy, “when you really love something, it doesn’t really matter if it’s huge, you’re just so proud to have made it. You know?” Amy really has a knack and she really outdid herself with this one.

DONALD: I haven’t watched it in years. I feel old, to be honest with you. But if it wasn’t for this movie I wouldn’t still have a career in the entertainment industry. It set all of us up. After that movie came out we all got a lot of opportunities, and we all appreciate that. When we see each other we’re like, hey man, you were there from the beginning, and I was there from your beginning. It’s a great camaraderie with a bunch of people who will never work together again.

BRECKIN (speaking in cast interviews, 2006): This guy came up to me and said, I went to rehab after seeing Clueless because I figured if Travis Berkinstock could go to rehab, I can go to rehab. It kind of blew my mind.

JUSTIN: My roots were in New York, and I wish that after the movie came out I went back to New York, went back to theatre and just kind of let things happen. I wish I hadn’t moved to LA straight away. If I could have done anything differently from a professional standpoint I would have gone back to where I came from.

WALLACE: Being a funny face, who can be recognised, I meet people on the street who are fans of various different things that I’ve done. I can tell the difference between a Clueless fan and other people that I meet. I never meet a nasty or insensitive Clueless fan.

MARCIA: I still have the Clueless poster hanging in my office. In the arc of my career, Clueless remains the film I am most proud of.

TWINK: But we were lucky, we were all lucky. It was just this moment in time when we came together as individual people to create something that became an iconic part of our lives. It’s a beautiful thing. Amy and I, going to the set everyday. It was just the best time. With Clueless, we were in our own country.