Get out your white collarless shirt from Fred Segal: Next month, Clueless turns twenty years old. **Amy Heckerling’**s film about a group of precocious teenagers has become a cultural phenomenon since its release—last year, Iggy Azalea turned her song of the summer into a shot-by-shot homage, and now there’s even a Broadway production in the works. But what s really remarkable about the Clueless success story is not its enduring popularity, it’s that everyone thought it was going to fail. “Everybody passed on it. Everybody said no,” writer and director Amy Heckerling told us by phone.
After being unceremoniously dropped by Fox, the film eventually landed at Paramount—and even the studio didn’t realize what they had on their hands. The sleeper hit would go on to inform the world about totally important designers, “Rollin’ with My Homies,” and launch the careers of several nineties darlings, including Alicia Silverstone, Brittany Murphy, and Paul Rudd. And two decades later, we’re still totally, butt-crazy in love with Clueless. “It’s weird, when it came out, I don’t think I had anybody interested in talking to us,” Heckerling said. “I don’t even know if we had a publicity day for Clueless. Now, without the studio even doing anything, every day someone’s calling about it.” With the valley girl comedy officially entering its twenties, we spoke to Heckerling about the myths and legends surrounding the perma-popular film. Below, fifteen things you never knew about Clueless.
“I loved her from [the Aerosmith videos] and when I met her I had these feelings, like, I just want to watch her. I want to take care of her. I think men and women will like her. She’s so pretty, she’s so sensual, and she’s also somebody that you seem to care for.”
“She had the script and she was doing her lines and as soon as I said ‘cut,’ the script woman and everyone in the crew started to walk up to her to tell her the right pronunciation and I had to run interference and go, ‘Step away from the actress. Stand clear of Alicia Silverstone.’ Because I didn’t want her to know that she had it wrong, I wanted that assurance without her thinking this is funny or a joke—which changes how you say things. There’s something you do when you’re completely confident that just can’t be replicated when you know you’re doing something wrong.”
Heckerling explained that Fox had a very different romantic plan for the pair: “They thought that Josh should be her neighbor, and that his mother liked her father,” Heckerling said. “He was next door and that’s why she never thought about him because he was under her nose.”
“Here we go again with the female shit,” Heckerling said. “They wanted me to have it be much more about the boys. And I thought, ‘This is inside a female’s head. How are we going to be in a boy’s room?’”
“At the time, when the studio sent out their DVD set of their movies to consider for the Academy Awards, we weren’t even included. And then it got nominated for a Writers Guild award and then they sent it out.”
“I never really had anybody in the script say her last name. And then the prop guys must have said, ‘Give us a last name.’”
“In one scene, Wallace [Shawn] was taking attendance and he sort of ad-libbed Horowitz. He just ad-libbed a last name. It’s not used anyplace else. In my script, she’s Cher.”
“She’s a buddy of mine and she was working with me and so I wrote the part for her.”
“I never read him, but I met with Dave Chappelle because I just loved him in Men in Tights. I was thinking of him for Murray. But once I saw Donald . . . he had such a little kid, puppy-like quality that was so perfect. And Dave is such a strong, manly, edgy person—I’m sure he could act like a puppy kind of guy—but Dave Chappelle wasn’t a little kid.”
“Any time I wind up in the lane where you can’t quickly turn off of it and it’s turning into the freeway, I just start screaming until I’m off of it.”
“Josh was the role I was having the most trouble with. Because that’s the one you fall in love with. He was so definitely the leading contender, but I still had more actors to see. Then I ran into him at a coffee shop kind of place and he had cut his hair. And I said, ‘What did you do?’ And he said, ‘Well, I didn’t hear from you.’”
“I thought she was really good. But once I saw Brittany, I was like, oh my god, I love Brittany.”
“The clog was problematic because we were going to hit Brittany in the head with the shoe, but you couldn’t really do that with one of the real wooden shoes—or even with a rubber bottom. So we made a lightweight foam clog. And it looked fine but it went by too fast—when you throw something at somebody, or kick a shoe off—you know, it happens in so few frames that you can totally not see it. So we slowed its trajectory down and we made it bigger and darker.”
“The principal in the movie who comes and introduces Brittany Murphy is the drama teacher and also teaches debate classes at Beverly Hills High. I sat in on his classes, his name is Mr. Hall, I named the character after him and he’s a great guy.”
“She was losing sleep. And then the yellow plaid came to her, and then she was able to sleep.”
