1. Searching for a boy in high school may be as useless as searching for meaning in a Pauly Shore movie, but conducting research at Beverly Hills High was particularly fruitful for writer-director Amy Heckerling. "The one thing I observed," she told Entertainment Weekly, "was these girls in a constant state of grooming."
2. Through various stages of editing, producers were frankly a bit clueless as to what to call their high school flick. Early titles included No Worries and I Was a Teenage Teenager.
3. Alicia Silverstone pretty much had the role of Cher in the bag. While writing her script, Heckerling took notice of the young actress cast in a string of Aerosmith videos. "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," she recalled to The Telegraph. Meanwhile her casting director friend Carrie Frazier "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."
4. Silverstone sealed the deal during a dinner out with Heckerling. "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," recalled associate producer Twink Caplan, who also gave life to Cher's sweet teacher Miss Geist. "And Amy thought: 'Oh my god, this is my girl.' Alicia was Cher, she is just the sweetest girl, she still is."
5. But while Heckerling was certain, she still had to heed orders from execs who wanted to cast a wide a net as posible. At various points in the process, "I saw Alicia Witt," she recalled in Jen Chaney's 2015 tome, As If!: The Oral History of Clueless, excerpted by Vanity Fair. "And who else? Tiffani Thiessen. The one that—she was in that show and she cut her hair and everybody was mad? Keri Russell, yes. Then they go, 'You've got to see the girl in [Flesh and Bone].' I never got to see her. I guess she was off on other things. That turned out to be Gwyneth Paltrow." Reese Witherspoon also campaigned hard—"Everyone said, 'This girl's amazing. She's going to be huge,'" Heckerling recalled—"But Alicia is Cher."
6. Other near misses included potential Joshes, Ben Affleck and Jeremy Renner, Lauryn Hill, who read for the part of Cher's bestie Dionne, Terrence Howard (Dionne's boyfriend Murray), Seth Green and Owen Wilson (considered for lovable stoner Travis) and Sarah Michelle Gellar, who was offered the part of perpetual fashion victim Amber. "There became a big negotiation for All My Children to let her out," co-producer Adam Schroeder revealed in As If!. "It was just for a couple of weeks, and they absolutely stuck their feet in [and] wouldn't let her."
7. Though it's next to impossible to imagine anyone but Rudd as Cher's adversary turned boyfriend, it almost happened, the studio nearly going with another star. But when that plan fizzled "we went back to Paul and he was screen tested, and he was amazing," casting director Marcia Ross recalled to The Telegraph. "He went through a lot to get that part, many many auditions."
8. Initially, though, he'd hoped to be considered for another role. "I thought Murray was kind of a white guy wanting to be Black. I didn't realize he was actually Black," he told Chaney in her 2015 book. "Also I thought: I haven't seen that character before, the white guy who's trying to co-opt Black culture. But, well: that character is actually going to be African-American. Oh, O.K."
9. The stickiest wicket in the casting process was finding the perfect guy to embody Cher's unrequited crush, Christian. "We'd auditioned so many people and it just wasn't right," said Ross, of struggling to find a guy who gave off their desired throwback vibe. When New York-based actor Justin Walker, entered the room: "You could just tell he had it. That was it. We didn't know who we wanted for Christian until then." Walker, who had mere hours to study the sides pre-audition, will always remember receiving the news. "I was managing a bar called the Overtime Bar and Grill, right next to Madison Square Garden, basically," he detailed in As If!. "I was speaking to my agent on a pay phone—a pay phone, mind you! And she told me that I got it, and I dropped the phone and started sprinting south on Eighth Avenue."
10. By comparison, casting lovelorn teachers Miss Geist and Mr. Hall was a relatively easy assignment. "I suppose they thought I was a good casting, I didn't have to audition," Wallace Shawn said of scoring his role as the movie's surprise romantic lead. "I actually had been a schoolteacher and so I knew some of that from the inside." As for Heckerling's associate producer Caplan, she didn't realize at first that she was being recruited for lovable Miss Geist. "I think she was based on a teacher Amy had back in school," she said of the part penned just for her, "and she thought I could portray her."
11. When the actor chosen as Cher's mugger bailed hours before his call, Heckerling was forced to scramble. "Nobody had mobile phones back then, I was literally calling everyone at their office and nobody was picking up," she shared. Actor Jace Alexander just happened to be working with producer Scott Rudin at the time, so "he got the role."
12. Breckin Meyer was particularly thrilled to score his part as Travis. At the time, he remembered to Entertainment Weekly, "I was in a really dry spell career-wise. I blew through any money I made as a kid doing commercials. I lived above a garage and I had no heat, no hot water and a mattress on the floor. I had to skateboard over to Seth Green's house to take showers and wash my clothes."
13. While not fully "ensemble-y challenged" then-17-year-old Silverstone wasn't quite as into fashion as her alter ego, admitting during a panel at the 2019 Chicago Comic and Entertainment Expo, that she sometimes struggled to relate to that aspect of Cher (who sported some 64 outfits during the 100-minute film) because she tended to wear "the same green T-shirt and jeans" all the time. Even during that initial 1995 press run, she admitted to the Allentown Morning Call, "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."
14. Figuring out each girl's style was a full week's work. "Usually you do two days, and we did seven, 10 hours a day of fitting," Stacey Dash told The Telegraph. "That's how many clothes we went through, racks and racks and racks." Her favorite: Dionne's plaid ensemble "with the hat that looks like a pretty little cake."
15. The chemistry between Dash and onscreen boyfriend Murray (a pre-Scrubs Donald Faison) "was there," she recalled to The Telegraph, "it wasn't acting." Certainly not on Faison's part. "I was enamored by her," he shared. "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!'"
16. It was, in fact, his first on-screen smooch. "When I said 'cut,' he just jumped around the set like crazy," Heckerling recently shared with the New York Post of the duo's post-traumatic freeway stress make-out. "He was bouncing around like a puppy. God, he was happy and proud."
17. The 40-day shoot in the winter of 1994 was not unlike the carefree high school experience they were trying to capture. "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," said Shawn. "It was totally delightful."
18. In fact, it wasn't uncommon to find the younger stars hanging out in each other's trailers. "We had a ball the entire time, it was kind of a dream," gushed Elisa Donavan (who scored the part of snobbish "Monet" Amber). "You're going to work with all people your own age, you're wearing crazy costumes and it was the beginning really for everybody." As for Faison, he recalls a lot of chill days rollin' with the homies. Sharing a trailer with Meyer, "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."19. For weeks after, he Meyer and Rudd "got so tight" that they all bunked together at Meyer's pad. "We'd watch Corey Haim and Corey Feldman movies every night," he detailed to EW, "and during the day we'd go out and try to get other jobs."
20. With the responsibility of carrying the film on her young shoulders, Silverstone had a different take than her supporting cast. "For me it was work," she said. "Everyone else came in and out, so they probably had a ball. But I was in every scene, working crazy hours. I was exhausted."21. Perhaps too tired to tend to one mess task. "Alicia had this little dog, and it would crap outside the make-up trailer," Caplan shared with The Telegraph, "people were complaining they were stepping in s--t. I had to say, 'Listen, can I get him a leash or something?!'"
22. When it came to filming one of the classic moments from that Valley bash, the cast kinda sucked. After struggling to make "Suck and Blow" work with an actual credit card, the prop team was tasked to craft one out of cardboard. Several layers of ChapStick provided extra suction.
23. Equally as tragic: Murray's shaved head—a look that had Dionne threatening to call his mother. Meyer revealed at the 2019 Chicago panel that they left a bit of hair on the sides of Faison's head—just enough to peek out when he was filmed in a hat.
24. Heckerling had a blink-and-you'd-miss-it cameo that saw her play a bridesmaid at Miss Geist's wedding. "I love Amy, which is why I forced her to be my bridesmaid in the movie," Caplan told the New York Post. "When I threw the bouquet, they weren't going at it enough, so Amy had to get in there and push everyone around. There's a shot of her pushing everybody."
25. Think Heckerling came up with Cher's signature slam on her own? As if! Something of an amateur linguist, the screenwriter is "always compiling slang words because I am just interested in how people use language," she explained to The Hollywood Reporter in 2016 of the line's origins. "At that time, which was like early '90s, 'As if!' was floating around in the gay community. and I thought it was really a multiuseful, multipurpose word. I thought it would be a good thing for teenagers to be saying."
26. While the phrase ranked in the outlet's 100 Favorite Movie Quotes, her personal favorite came from the Cher's impassioned debate class speech: "I guess, in a goofy way, I have always been proud of 'It does not say RSVP on the Statue of Liberty.'"27. Crafting the full lexicon required some thoughtful research. "When I auditioned the kids, I'd always ask for new words," she told Entertainment Weekly. "That's where I got 'going postal.'" As for other terms, "'Betty' was based on Betty Rubble, who was very pretty," she shared. "And 'Barney' is like, How did he get her?"
28. But one of the film's classic moments came from Silverstone herself. Giving her (still incredibly relevant) debate argument on immigration, she mispronounced Haitians, Heckerling shared with EW, "and everybody started to run up to her to tell her it was wrong. I had to stop them. It was much funnier the way she said it. That was Cher."
29. It truly is hard to nail down just one "best" moment from the flick. For Dash, it "was when we shot the tennis-court scene, when Elisa Donovan says, 'My plastic surgeon doesn't want me doing activity where balls fly at my nose.' And I say, 'There goes your social life.'" But Silverstone is partial to Tai's classic "You're a virgin who can't drive" slam: "The way her little mouth gets puckered up and the way she says it, it kills me. That was way harsh, Tai."
30. If you ask Rudd, there's no way Cher and Josh are still together (after all, they lived in California, not Kentucky), but Silverstone has a more optimistic take. "Hopefully she's married to Paul Rudd and has children and works hard at something she loves a lot," she opined to Entertainment Weekly. "Maybe she's a professional organizer. Whatever she is, I don't think she's annoying anymore." Herckerling imagines her creation as incredibly woke. "First of all, she'd want people to wear masks," she told The A.V. Club of 2020 Cher. "She would be for equality, equal pay, immigration reform, prison reform—the environment and climate change and evil corporations poisoning our food supply and the air and the water. I mean, boy, where do you start?"