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‘Clueless’ 25 Years Later: These Are Writer Amy Heckerling’s Favorite Lines

Iconic coming-of-age teen comedy was released in theaters on July 19, 1995

It’s been 25 years since “Clueless” hit the big screen, so director and writer Amy Heckerling spoke to TheWrap about how the film came together, where she thinks Cher would be now and that controversial love story between Cher and her stepbrother Josh.

Ultimately, Heckerling wanted to do a film about the “in” crowd while also painting the world in the way that she wanted to see.

“It wasn’t like I was doing something that was based on anything real, I was making up a world that I liked and that’s the way I want the world to be,” Heckerling told TheWrap about why she made the film. “Everyone is equal. I just wanted this fake world that you would see in a comedy of manners about the turn of the century — something more beautiful and happy than what really is.”

“Clueless” starred Alicia Silverstone, Stacey Dash, Paul Rudd and Donald Faison, and was written and directed by Heckerling. It followed a group of Beverly Hills High School teenagers navigating popularity, love and life together.

“Clueless” hit theaters in 1995 and grossed $56.1 million in the United States. Since then, it has developed a cult following and has been followed by a spin-off TV sitcom, a musical and a series of books.

Read TheWrap’s Q&A with Heckerling below.

TheWrap: How did you get involved with the movie 25 years ago — tell me about the process of how it all started.

Heckerling: Pretty much I was going, “it’s all over now, I did a movie that made a bunch of money, which was ‘Look Who’s Talking’ and my life is over.” And I had to make a sequel, and I was like, “nothing good is ever going to happen again.” You get offered stuff that you don’t like or get pressured to do something you don’t want to do, but when you’re not offered stuff, you get mad. I was like, “what do I want to do? What makes me happy?” I was thinking about “Fast Times at Ridgemont High” and the character not being aware when people were mad at him, it just didn’t occur to him that everybody wasn’t okay with him and didn’t like the same things he did. I thought, that’s such a positive thing. Then, I remember reading  “Gentlemen prefer Blondes” and how she just assumed all men were in love with her and someone that’s imperfect narrating the story.

Positivity fascinates me — I don’t understand it. I’m very curious about how that could be, so I started to think about a character that would be so happy and sure things would work out and what would their life look like? I started playing around with that, and I went into the studio to pitch a TV idea I had and they told me all these people came in pitching stories about young people that were the nerds and the depressing people and they wanted to do something about the “in” crowd. I said, “alright, but can I make them a little wacky?” And they said, “yeah.” So then I started combining what I was fascinated with, with what they were looking for and sort of developed the Cher character.

It started out as a pilot for 20th Century Fox and things weren’t happening and I was annoyed and I switched my agent and I got this guy, Ken Stovitz, and TV people had passed on my pilot, and I gave him things I had written recently and he read that and he said, “this should be a feature.” We went back to Fox and said, “here’s the material that you already own because the TV people have it. And here’s how it could be a feature.” I wrote the first few drafts for them and then I started thinking,  what would be the three-act story that would work for her, and I started to think of longer forms that had positive characters, and that’s when I thought of Jane Austen and “Emma” and reread that. I loved it when I read it in college — it’s the most modern story with the most perfect character, the most lovable, flawed person that you’re rooting for. Then I looked at what could make the bones for the present day high school teenagers, and if I ever thought like, wait, how would this happen, I would just go back to “Emma” and there were the answers. 

How many people did you see for the main roles, and how did you ultimately land on Alicia Silverstone for Cher?

I was on the treadmill and she was in the Aerosmith “Cryin'” video and something about her just hit me that I had to jump off the treadmill, find a VHS, put it in the machine and record the video. Then I had the person in my brain.

I met people who were out there at the time and I had talked to Mel Brooks who had just done ‘Men in Tights,” and there was a guy in there that I thought was amazing, Dave Chapelle, and Mel couldn’t be more effusive and saying, he’s going to be so big, he’s amazing… I met Dave at a restaurant and he blew me away but I was looking for someone who was a totally naive puppy, and Dave Chapelle was such a mensch, not to say he isn’t a wonderful actor. When I met Donald Faison, he was a whippet, he just had that wonderful, energetic, innocent, fun spirit but then when he attached to read these long speeches that showed his extensive vocabulary and that he was actually really smart too, but that wasn’t the side he was pushing. It felt like he was Murray.

Stacey Dash came in and read and I wanted someone who could be the queen of a country somewhere and she had that regal bearing.

Where did this film and such a specific world you created come from?

It wasn’t Beverly Hills High School, it was Bronson Alcott High School. It wasn’t like I was doing something that was based on anything real, I was making up a world that I liked and that’s the way I want the world to be. Everyone is equal. I just wanted this fake world that you would see in a comedy of manners about the turn of the century — something more beautiful and happy than what really is.

On his “Scrubs” podcast, Donald Faison told a story about the decision to give his character braces because he had these baby teeth. Do you remember that?

It’s always tough because you’re like, how long will these be in, but it was such a good look for him. You could say some hardcore slang or rap stuff but then he’d smile with those braces and you’d be like, aw… like when your 5-year-old says something sophisticated, it undercuts it — it’s so sweet. 

Could you have anticipated how iconic the film would be 25 years later? It remains one of the most quoted films to date.

That makes me so happy. When someone told me that their daughter and her friends decided to go as Cher and Dionne for Halloween, I was like, oh my God, I f–king love that.

Do you have a favorite line, quote or saying?

“Keeping it real” came from Donald. The cast would come in with things where I was like, “yes, that’s brilliant!” Then there were things that came from my parents, an angry Jewish couple yelling at each other.

You know, I was at the Museum of Modern Art and I heard someone quote the Monet part (“She’s a full-on Monet. It’s like a painting, see. From far away it’s okay, but up close it’s a big ol’ mess.”)

I have to give props to the UCLA linguistics department — they published a list of slang words and phrases, and Monet came from that. You keep your ear to the ground and you do research and you hear things, and a lot of things came from gay friends, from rap songs, from linguistics, from old slang dictionaries, and old movies and songs. 

Is there anything that you look back on and think, “dang I wish I’d done that differently, or that doesn’t age well or hold up”?

I don’t watch it a lot. Every time I see pieces of it on TV, I think, “good God, I think it should’ve moved much faster.” But I feel that about everything. It was 90 minutes? Comedies should be that length.

Let’s talk about how the technology of Cher’s closet pretty much still doesn’t exist today. How did that come about? 

I mostly wear sweats as a writer and when I have to go somewhere, I always have to think about what I would look good in. Why can’t I just have pictures like when I had cutouts when I was little and do it like that, and then I wouldn’t have to try on my clothes? Then I thought I could do it on a computer — it’s doable, that would be a good use of computer technology. 

25 years later, what do you think Cher’s life looks like?

Well, she would’ve been married to Paul Rudd. I would expect she’d be a do-gooder, which is not far from where Alicia Silverstone has landed. Sometimes she says things where I’m like, “no no no,” but for the most part, she has the biggest heart. If you’re thinking Cher went into fashion, I don’t think so. She was much more into the Pismo Beach disaster.

Let’s talk about the love story between Cher and her stepbrother. Did that come with any complications? Did you get any pushback for anything included in the movie? 

Oh yeah, from the first studio, but not from Paramount. I thought, they’re not blood-related at all and he was briefly married to her mother and they are not related at all. In the traditional rom-com, you realize the person under your nose is the person you should be with.  That’s the way it always is in movie world. They were so close to each other, they knew what was lovable about each other. I felt very strongly that that was how it should be. 20th Century Fox was like, “that’s disgusting” and I was like, “why, it’s not incest because my grandparents were step-siblings and within the Jewish ghetto it wasn’t a man or woman, you don’t stay single and see what’s the best person you can get.” You were expected to find somebody because kids ned parents and you’re in a world that’s only people in this world. There was a widow and a widower and they got married and they had kids.

Do you have a favorite high school movie? What about a favorite modern-day literary adaptation? 

I saw the recent “Emma” which I thought was wonderful. There were others that I wasn’t as crazy about. The one with Anya Taylor-Joy was amazing and the director did an amazing job. What was used from the story was amazing. There are other teen movies that I love: “Booksmart” I thought was great, “The Edge of Seventeen.” My favorites of all time are “The Loneliness of the Long Distance Runner,” “A Clockwork Orange,” “American Graffiti…” but I guess those aren’t high school movies.