Teen comedies have been around since Frankie and Annette played beach-blanket bingo in the early ’60s. And for the most part, they’re as disposable as a tube of Clearasil. But every once in a while, one sneaks up and comes to symbolize a generation of kids — how they talk, how they dress, how they see the world. Amy Heckerling, who directed 1982’s Fast Times at Ridgemont High, already knew something about that when she decided to spin Jane Austen’s Emma into a cotton-candy confection about Bettys, Baldwins, and a ritzy, ditzy Beverly Hills rich girl named Cher Horowitz. Still, no one — not even Heckerling — predicted that the little $15 million high school satire that every studio in town had passed on would become so much more than just another teen comedy. When Clueless opened in July 1995, it was a modest hit, landing in second place well behind Apollo 13. But over the past 17 years, it has snowballed into a coming-of-age classic, launching a thesaurus full of quips like ”As if” and ”Whatever.” The movie’s cast of fresh-faced unknowns are all grown up. Many of them are now parents themselves. But when they reassembled in July for a class reunion, it was clear that — unlike for some of us — high school was the best time of their lives.
Amy Heckerling (Writer-director) Originally, it wasn’t called Clueless. It was Clueless in California. Before that, it was I Was a Teenage Teenager. And before that, when I first pitched it as a TV show, it was called No Worries. Twentieth Century Fox said they wanted a show about teenagers — but not the nerds. They wanted it to be about the cool kids. The most successful character in anything I’d ever done was Jeff Spicoli in Fast Times. People think that’s because he was stoned and a surfer. But that’s not it. It’s because he’s positive. So I thought, ”I’m going to write a character who’s positive and happy.” And that was Cher.
Twink Caplan (Associate producer/Miss Geist) Amy and I were best friends. She’d put me in her film Look Who’s Talking. When we showed No Worries to Fox, it was obvious they didn’t get it. They thought the script needed more boys in it. They were afraid that if they focused on girls, we wouldn’t get any guys to see it. So it went into turnaround. It was dead.
Heckerling I remembered reading Emma in college and being struck at how much it reminded me of old TV shows like Gidget. There’s something so basic about it. I knew it would be set in Beverly Hills because it’s a hyper-pastel fantasy place. I hung out at Beverly Hills High School for research. And the one thing I observed was these girls in a constant state of grooming. Anyway, after a couple of [teen-targeted] movies like PCU and Airheads came out and didn’t do so well, Fox got scared. Everybody in town pretty much passed on it. Then it somehow made its way to [producer] Scott Rudin, who had a deal at Paramount. He got it. There wasn’t any mandate to get a big star. The feeling was that I would find people.
Caplan We auditioned everybody. It was like it was Gone With the Wind and everybody wanted to be Scarlett. I remember Reese Witherspoon came in to audition to play Cher.
”Heckerling” A casting-director friend was pushing me to get the girl from The Crush, but I really wanted the girl from the Aerosmith videos. Then I saw The Crush and realized they were the same girl.
Alicia Silverstone (Cher Horowitz) I met Amy at this little café in Beverly Hills, and I remember she was really taken with the fact that I was drinking a drink with a straw and I wouldn’t bring the drink up to me. I kept moving my head to the table to get to the straw. She loved that for some reason. I remember I read the script in a limo driving back from shooting the third Aerosmith video — the one I did with Liv Tyler. At first I didn’t like Cher. I thought, ”Who is this girl?” I had nothing in common with her at all. I thought she was a materialistic, annoying little bitch. But then I saw that she cares about her daddy so much and she’s trying so hard to help people and do these good things. So maybe she wasn’t such a bitch after all.
Paul Rudd (Josh) When I first read the script, it took me a while to get it. I remember thinking, ”Ugh!” Because I’d been reading so many pilots and bad versions of teen movies. It wasn’t until I got many pages into it that I thought, ”This is actually smart.” I thought Justin Walker’s character, Christian, was a really good part. It was a cool idea, something I’d never seen in a movie before — the cool gay kid. And then I asked to read for Donald Faison’s part, because I thought he was kind of a funny hip-hop wannabe. I didn’t realize that the character was African-American.
Donald Faison (Murray) I read with Lauryn Hill in an audition in New York. Afterwards she said to me, ”I’m not sure it’s going to work for me, but I think you’ve got a really good shot at getting it.” Then they flew me out to L.A. to read with Stacey Dash. They told me, ”The part’s yours, just don’t blow the audition!” I kind of based Murray on a guy who wanted to be Ice Cube’s character in Boyz n the Hood.
Stacey Dash (Dionne) I actually read with Donald and Terrence Howard. It’s funny, because I was older than everyone else. I was 27 and I was playing this high school student, and I had a son at home who was 6 years old.
Breckin Meyer (Travis) I was in a really dry spell careerwise. 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. When I went in to audition, I lifted from my favorite people — Sean Penn from Fast Times and Keanu Reeves in Bill & Ted’s Excellent Adventure. It seemed like every young actor in town was up for a part. I remember seeing Jeremy Sisto in there and thinking, ”Damn!” He was a real up-and-coming guy — a real Robert Pattinson type.
Jeremy Sisto (Elton) I was 19 and had done a handful of studio movies that were all kind of unsuccessful. Alicia and I had done a movie together right before Clueless called Hideaway, and I played a serial killer hunting her down. I could have auditioned for Paul’s role, but for some reason I was going through a phase of not wanting to play nice guys. I just thought Elton was funny. The rest of them thought they were good people, but he was a guy who didn’t even try.
Justin Walker (Christian) They were having trouble finding someone for the part of Christian. As far as him being gay, I was aware of the consequences it might have for my career — how I might be perceived afterwards as ”the gay guy from Clueless,” but I didn’t care. I’d never been in a movie of any kind, and it was an honor. I would do the part again tomorrow.
Elisa Donovan (Amber) I knew exactly who Amber was, and I based her on these girls that I couldn’t stand in high school. When I got the part, I didn’t know what to do, because I had a role on Blossom at the time. My dad said, ”Wait a minute, you have this TV show, why would you go and do a movie? Who’s in this movie?” And you couldn’t say anyone famous, because no one was famous.
Wallace Shawn (Mr. Hall) My role was drawn from life. I was a schoolteacher — it’s actually the only legitimate job I’ve ever had. I taught for one year in India, and I taught at a private school in Manhattan for two years. Being a teacher in the movie was easier because there was a script.
Heckerling For Cher’s father, I was looking for someone who might play a hitman in other movies. It doesn’t occur to Cher that he’s scary.
Dan Hedaya (Mel Horowitz) I’ve done a few roles that are on the other side of the law, but I’m an uncle many times over and I like children very much.
Heckerling For Tai, we wanted someone who was a real New York slobby type, which is what I am. Then Brittany Murphy came in, and you just felt like, ”Yeah, that’s it. We’re done.” When I auditioned the kids, I’d always ask them for new words. You know, slang and stuff. That’s where I got ”going postal.” I loved calling someone a ”Monet.” From far away they’re f—ing gorgeous and up close they’re totally different. ”Betty” was based on Betty Rubble, who was very pretty. And ”Barney” is like, How did he get her? ”As if” came from the lesbian community. Any outsider group is going to create their own language — whether it’s homosexual, black, prisoners, or cabdrivers. You just have to be willing to open your ears and listen.
Faison I had no idea what the hell I was saying. What the f— is a ”Monet”? What’s ”going postal” mean? And when they explained to me what it meant, I thought, ”That’s really messed up!” Amy just gets the way teenagers speak and what they go through. We all had crushes on her, especially Breckin Meyer. Ask him about it, he’ll tell you.
Meyer I had the hugest crush on Amy. She was this beautiful sprite goth Japanimation-looking adorable raccoon-eyed beauty.
Silverstone I didn’t know what anything meant. I would have to say to Amy, ”What does ‘As if’ mean?” She’s way hipper than I am. I mean, ”Surfing the crimson wave”? At the time I remember when I would go to the wardrobe fittings, I was like, ”God, why do I have to go to another fitting?” When I read the script, I understood that Cher really likes clothes, but that doesn’t mean that you understand that you’re going to have to have 67 different outfit changes. My little brain couldn’t understand why her clothes were so important to her. By the end, of course, I wanted all of them.
‘Heckerling The first day, we shot the scene in debate class. And Alicia said the Hate-i-ans instead of ”Haitians,” 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.
Shawn I think in a funny way Alicia wasn’t even aware of what a big responsibility it all was until it was over. The fact that this was a major motion picture with a real budget, I don’t think Alicia thought about that.
Silverstone For me it was work. Everyone else came in and out, so they probably had a ball. But I was in every scene, working crazy hours. I was exhausted.
Faison It was inspiring that a kid her age [Silverstone was 18 during filming] was able to carry a movie like that. Because when we were making the movie, you don’t think the movie’s going to be good. You think, ”I’m making the next License to Drive.” You think this movie’s going to be just for teenagers and that’s it.
Dash My favorite day was when we shot the tennis-court scene, when Elisa Donovan says, ”My plastic surgeon doesn’t want me doing any activity where balls fly at my nose.” And I say, ”There goes your social life.” I love that line.
Silverstone I think my favorite moment in the entire movie is when Brittany says to me, ”You’re a virgin who can’t drive.” The way her little mouth gets puckered up and the way she says it, it kills me. That was way harsh, Tai.
Meyer Brittany and I did King of the Hill for eight years together. And we played boyfriend and girlfriend two or three times after Clueless. Brit is…I say ”is” because it still feels weird to say ”was.” [The actress died suddenly in 2009.] Brit’s unbelievable. I first met her when she was 12, on a Dabney Coleman show called Drexel’s Class. And we would see each other all the time as kids growing up in the Valley. When I saw her at my Clueless audition, I let out a huge sigh of relief, because I already loved Brittany. I didn’t have to act being in love with her. Once you met her, you couldn’t help it. In the movie, in the wedding scene at the end, we’re supposed to have this kiss. And when I go to kiss her, I had to do it on the top of the head because I felt like her big brother.
Sisto Right when the movie was about to wrap, I remember asking Breckin and Donald, ”Do you think anyone’s going to see this?” We had no idea.
Faison When the movie was over, we got so tight that Paul and I stayed at Breckin’s place for a couple of weeks. We’d watch Corey Haim and Corey Feldman movies every night, and during the day we’d go out and try to get other jobs.
Rudd If memory serves me right, we watched the Coreys in Blown Away. I don’t even know if it was night; we might have watched it during the day. That’s how sad it was.
Heckerling We had a test screening, and it wasn’t astounding. It peaked with females. And I was like, ”Oh, no, I just made a movie for girls.”
Faison Me, Alicia, Paul, and Breckin went to a preview screening. The audience was really into it. It felt like, ”Wow, we did it! I’m part of something like the Anthony Michael Hall and Judd Nelson movies I grew up with.” I run into grown-ups now who are like, ”Dude, Clueless was my s—!” It’s their Breakfast Club.
Heckerling Before Clueless came out, I never got any respect. I felt like Rodney Dangerfield. Nobody ever said nice s— about me. And when I read the reviews it was so nice. It was like, ”Finally!”
Rudd When people interviewed us at the press junket afterwards, all of them said, ”I thought I was going to hate this movie and I wound up having a blast!” We heard that a lot. Then Scott Rudin called to say ”Congratulations” and that I shouldn’t get used to it because they aren’t always like this. So appreciate it. It’s really all Alicia. You look at her and you think, ”That person is a star.” You can see why little girls would want to be her and why guys had crushes on her. Afterwards, every guy I met was like, ”Dude, you got to make out with Alicia Silverstone!”
Silverstone When I first started out, people would say, ”Hey, that’s the girl from The Crush.” And then I was ”the Aerosmith chick.” After Clueless, it changed. It was suddenly ”That’s Alicia Silverstone.” It made it nicer to be yelled at. But it was intense. It’s nothing you can ever be prepared for. I didn’t know what hit me.
Hedaya I never anticipated that it would become so iconic. Oftentimes a father comes up to me and refers to the line I said to the punk kid who comes to pick up Alicia on a date: ”I have a .45 and a shovel. I don’t think anyone would miss you.” A lot of men have told me, ”I wish I had said that.”
Meyer Someone came up to me once and — very serious and teary-eyed — said, ”I just want you to know that when I saw Clueless and I saw Travis decide to go into a 12-step program, that’s when I decided to get sober.” There was a part of me that was like, ”Wow, that’s amazing.” And there was another part of me that was like, ”Are you serious? Because I’m pretty sure Travis might have relapsed. But I’m happy you found that.” I don’t know how to explain why something gets embraced. The movie is just fun, and it looks like the best-tasting bubble gum ever. Whenever someone recognizes you from Clueless, there’s almost like a different look in their eyes than just ”Hey, you’re that dude!” People are like, ”Man, that movie meant so much to me.”
Silverstone It’s one of those movies that people watch over and over again. I think it’s just one of those things that makes you feel really good. I mean, Jane Austen isn’t such a bad writer. You could watch it now and it doesn’t feel dated. If I was in a hotel room and it came on, I’d want to watch it.
Dash I have a 9-year-old daughter, and soon I’m going to let her watch it. I actually have a Dionne Barbie that I got on eBay for 60 bucks that she plays with.
Heckerling I really can’t say why it’s held up for 17 years now. You just enter this world and see these characters and hear this music, and even if you know the story, you just want to live there for a little bit. Being a teenager is an important time of life. It’s when you’re figuring stuff out. It’s the most romantic time of your life, and it’s when you figure out who you are. And I don’t think that that’s less important than anything else.
Silverstone Where’s Cher now? Jeez. Hopefully she’s married to Paul Rudd and has children and works hard at something she loves a lot. Maybe she’s a professional organizer. Whatever she is, I don’t think she’s annoying anymore.
Rudd No, I don’t think they’re still together. I would be surprised. But what the hell do I know?
Update: The Clueless Cast and Director
The 60-year-old writer-director’s latest comedy, Vamps, comes out Nov. 2. It stars a pair of familiar faces: Alicia Silverstone and Wallace Shawn.
In addition to Vamps and this month’s comedy Butter, Silverstone, 36, will appear in The Performers on Broadway this fall and is the author of The Kind Diet: A Simple Guide to Feeling Great, Losing Weight, and Saving the Planet.
The actor, 43, has been in a string of hit comedies such as Anchorman: The Legend of Ron Burgundy, Knocked Up, and Role Models. He is currently in the play Grace on Broadway, and will star in Judd Apatow’s This Is 40 (out Dec. 21).
The 45-year-old actress reunited with Heckerling in the 2007 film I Could Never Be Your Woman. She recently starred on the VH1 series Single Ladies.
Faison, 38, starred for all nine seasons on the medical sitcom Scrubs. He’s currently filming the superhero sequel Kick-Ass 2.
The 38-year-old actor has built a successful TV career over the past decade, starring on Six Feet Under, Law & Order, and the current ABC sitcom Suburgatory.
Meyer, 38, has continued to act on TV (TNT’s Franklin & Bash) and in movies (Ghosts of Girlfriends Past). He also writes for and lends his voice to the cult stop-motion animated series Robot Chicken.
The 44-year-old actor now serves on the board of such philanthropic organizations as the Hollywood Dell Civic Association and the Cheremoya Foundation.
Donovan, 41, recently starred in the Hallmark Channel movie Your Love Never Fails. She will also appear in the TV movie The Dog Who Saved the Holidays this fall.
The 68-year-old Shawn has lent his one-of-a-kind voice to the dinosaur Rex in the Toy Story movies and recurs on The CW’s Gossip Girl. He can next be seen in Heckerling’s Vamps.
The actress and producer, 64, still works in film and TV. Her most recent movie was the 2012 comedy Tim & Eric’s Billion Dollar Movie.
The 72-year-old actor recently played Congressman Barney Frank in the 2011 HBO movie Too Big to Fail.