By 
1. Cher and Josh's step-sibling relationship was based on the relationship between writer/director Amy Heckerling's grandparents.
Heckerling's grandparents were stepbrother and stepsister whose widowed parents got married. "Totally not blood-related," Heckerling explains in the book. "When I was a kid all she did was complain about her stepmother to me ... but her step brother, whom she later married, was always a protector. They were married. They knew each other from the time they were teenagers. They were so dependent on each other and so angry all the time with each other. Anyhow, that cracked me up. So it did not seem like a crazy thing to me [for Josh and Cher to be together]."
2. Alicia Silverstone an on-set napper.
Her castmates remember her catching naps for minutes at a time between takes. Like in the driver seat during her scene with Ron Orbach aka the Messiah of the DMV. "Alicia's sitting in the driver's seat," he says. "Again, eyes closed, looking like she's sleeping or something, I couldn't tell. But when action is called, her eyes open, she goes, and it's basically spot-on: hits every line, every moment, perfectly. 'Cut!' And she goes back to sleep."
3. Costume designer Mona May avoided dressing characters in black.
Clueless's aesthetic was relatively simple: fun, carefree, and in the words of Heckerling, "slutty was not a part of it."
"They were teenage girls that couldn't drive yet," she elaborated. "There were skateboards, druggie stuff. But nobody was wearing bondage-y shit or overtly cleavage-y things." Adds May, "She wanted the palette to be really happy, very vibrant. I think there are maybe two or three, maybe four things, that are black."
4. Alicia Silverstone never remembered to take her makeup off at the end of the day, and it would make her break out.
Silverstone was like any other teen: She, too, was guilty of not removing her makeup every day. (Impressively, this seemed to be the only real point of contention — if you could even call it that — during filming, at least according to As If.) Makeup supervisor Alan Friedman said producers confronted him about Silverstone's increasingly temperamental skin, and he essentially told them, duh — she's not following the skin care regimen he'd given her. "'Well, you take her and you tell her,'" he recalls them saying to him. "I said, 'No, no, I'm not her mother. You know, I gave her the — she has a set of stuff in her trailer and she has a set of stuff at home.' 'Then make her take everything off before you go home.' All right, fine. So that lasted a day." In other words: We are all Cher Horowitz.
5. Tara Reid made a cameo at the Val party (off-camera, sadly).
Donald Faison (who played Murray) recalls:
It took a long time to shoot that [party] scene and I remember falling asleep [at one point] and being woken up by Tara Reid, who was not in the movie but just came by the set to hang out which was really odd. I went to high school with Tara Reid, so when she woke me up, it was kinda like, "Yo, what are you doing here?"
6. The couple you see making out in the pool at the Val party wound up getting married.
The Val party didn't just breed a Coolio hook and a bad night for Cher Horowitz: It's actually the reason a real-life couple ended up together. "The ADs and I were going through saying if any of the extras wanted to play a couple in the swimming pool making out, they would get extra money for that because they would be wet," Heckerling tells Chaney. "A couple of people volunteered, a cute guy and a cute girl. And I thought, 'Well they'll make a cute couple.' So we asked them if they wanted it, and they looked at each other and thought, 'Yeah okay.'
"Years later I was walking down Melrose and I hear some people going, 'Amy! Amy!' And I turn around, and it was them. They met that night. They're engaged. She shows me the ring that's been in his family. I don't know how that marriage worked out, but it was really sweet."
7. Paul Rudd almost missed the Mighty Mighty Bosstones scene ... because he nearly got shot the night before.
The night before filming at the Bosstones party, Paul Rudd almost met an untimely fate. After dinner with friends, a man jumped out in the parking lot, put a gun to his head, and demanded money. "He goes, 'You don't think this is a real gun?'" Rudd remembers. "He was all tweaked out on something, and he shot his gun next to my head. And I just remember looking out of the corner of my eye, and [my friend] had gone back inside — she saw what was happening — to get those policemen [who they'd seen inside]. She did, but it was too late. Then they went to try and chase him, but they couldn't find him."
The guy took off with the actor's backpack, which had a Discman (it was the '90s!) and a copy of the script in it. And that's how Ant-Man was born.
8. During filming, Amy Heckerling was dating Perfect Strangers Bronson Pinchot; he in part inspired the name of Cher's high school.
Bronson Alcott High School got its name from Balky of Perfect Strangers, Bronson Pinchot, and Bronson Alcott, the father in Little Women, who Heckerling describes as one of the era's "freethinkers" and "into educating women." However, Pinchot didn't handle his partner's fame entirely well after he was eclipsed during Clueless's premiere.
"... Somebody told [the red carpet photographer] that I was the one who made the movie," remembers Heckerling. "Then they were going, 'Oh, Amy: over here! Oh, Amy: over here! Bronson, can you move out of the way?' And this is basically stupid, showbiz stuff, but Bronson's quite a sensitive person. I had to deal with the effect that that had on his psyche for a while."
Not cool, bro.
9. Elisa Donovan, who played Amber, tried to make her "action figure" doll look more realistic.
In an attempt to make her Amber doll anatomically correct, Donovan actually approached Mattel executives, hoping to make the figure look more like her and less like, well, Barbie. "I'm still very outspoken about women's issues and anorexia and eating disorders and I felt like, I don't want to perpetuate this idea," she says. "So can't we make it so that they look like our body shapes? And they looked at me like, 'You must be smoking crack.'"
10. GLAAD gave Heckerling well-deserved kudos for Christian's role
As you probably remember, Christian (played by Justin Walker) was Cher's dream man until she realized he was gay. Instead of making it a thing, Heckerling opted for Cher to find out, accept it, and move on — with Christian becoming a mainstay in her life and the reason Tai doesn't fall to her death in the mall. Understandably, GLAAD was pleased. "I got a letter from GLAAD that was very happy," Heckerling shares. "[Christian] stood up to the bullies that could have possibly hurt Tai. They were glad to see he was doing something brave besides, you know, he's my new shopping friend."
"What people called me was, for the most part, 'He's the gay guy from Clueless,'" Walker says. "I'm not here to tell you that it kept me from getting parts at all. I'm here to tell you that it was a factor in every part of my life. Would I do it again? The answer to that question is, without hesitation. [I would do] it for me, and for the movie, and for what it might have meant to other people and other roles and teenagers questioning their sexuality at that point in the lives."
Follow Anne on Twitter.
All facts and quotes are from the new book As If: The Oral History of Clueless, by Jen Chaney. You can buy the book here.
