With loads of sass and style, Clueless won the hearts of a generation and became one of the most beloved coming-of-age comedies of all time. But even if you're a total Betty or Baldwin, you probably don't know all the juicy details behind Clueless, which hit theaters 20 years ago today.
1. CLUELESS IS MODERN-DAY JANE AUSTEN.
Writer-director Amy Heckerling found her inspiration for Cher's bumbling journey of love from Austen's classic 1815 novel Emma. "I remembered reading Emma in college and being struck at how much it reminded me of old TV shows like Gidget," Heckerling recounted to Entertainment Weekly. "There's something so basic about it."
2. THE DIRECTOR STUDIED REAL BEVERLY HILLS HIGH SCHOOLERS.
Heckerling wanted to spin her combination of Emma and Gidget in the setting of a Beverly Hills high school, which she envisioned as a "hyper-pastel fantasy place." To create the movie's totally quotable dialogue, Heckerling sat in on classes to get a feel for how teens in the '90s talked. But Cher's classic "As if!" actually came from the lesbian community. "Any outsider group is going to create their own language—whether it's homosexual, black, prisoners, or cab drivers," Heckerling explained. " You just have to be willing to open your ears and listen."
3. THE "HAITIANS" MISPRONUNCIATION WAS ALL SILVERSTONE.
You know how Cher rallies for America opening its borders to the Haiti-ans? The script read "Haitians" and Silverstone made an honest mistake. But before producers could rush in and correct her, Heckerling demanded they let her go. "I had to stop them," she remembers. "It was much funnier the way she said it. That was Cher."
4. REESE WITHERSPOON COULD HAVE BEEN CHER.
Witherspoon already had a few film roles to her credit with The Man in The Moon, A Far Off Place, and Jack The Bear. Silverstone only had the Lolita-like horror movie The Crush on her feature filmography. But with no pressure from the studio to cast stars, Heckerling had the freedom to pick the ingénue whom she felt had "that Marilyn Monroe thing" that captured "a vague notion in my head of Cher as a pretty, sweet blonde, who, in spite of being the American ideal, people still really like."
5. SARAH MICHELLE GELLAR WAS OFFERED THE ROLE OF CHER.
But the eventual Buffy The Vampire Slayer star had to turn it down because of scheduling conflicts with All My Children, on which she appeared from 1993 to 1995, playing Kendall Hart Lang.
6. ALICIA SILVERSTONE HAS AEROSMITH TO THANK FOR CLUELESS.
Heckerling's casting director first pitched Silverstone for Cher based on her performance in The Crush. But Heckerling wanted that fascinating blonde girl from the music video for Aerosmith's "Cryin." Lucky for Silverstone, she was one and the same. She went on to do two more Aerosmith videos, "Amazing" and "Crazy."
7. CLUELESS LAUNCHED ALICIA SILVERSTONE'S FILM CAREER.
Yes, she was on the rise with her role in The Crush and her growing fame from the Aerosmith videos. But it was Clueless and its evolving cult status that made Silverstone a household name.
8. PAUL RUDD WANTED TO PLAY CHRISTIAN ... OR MURRAY.
Though he was ultimately cast to play Cher's brainy stepbrother Josh, Rudd had initially wanted to portray Christian. He was intrigued by a Hollywood script having a "cool gay kid" character. When that didn't pan out, he asked to audition for Murray, a role that ultimately went to Donald Faison. Rudd told Entertainment Weekly, "I thought he was kind of a funny hip-hop wannabe. I didn't realize that the character was African-American."
9. JEREMY RENNER COULD HAVE BEEN THE OBJECT OF CHER'S AFFECTION.
Renner auditioned for the roles of both Christian and Josh, but lost out to Justin Walker and Paul Rudd, respectively.
10. LOTS OF TODAY'S STARS AUDITIONED FOR CLUELESS.
With so many characters to cast and not much of a budget to brag about, the casting calls spread throughout young (and then unknown) Hollywood. Terrence Howard and Lauryn Hill read for Murray and Dionne, respectively. Owen Wilson tried out for Travis. Leah Remini auditioned for Tai, while Zooey Deschanel went out for both Amber and Cher.
11. BRITTANY MURPHY WAS ACTUALLY THE VIRGIN WHO COULDN'T DRIVE.
Looking back on Clueless and its legacy, the late Murphy recalled, "It's hard for me to believe it's been 10 years since that movie. I really was a virgin who couldn't drive. I was living in an apartment in the Valley with my mom—and I remember starting to see these huge billboards of us all over town. It was amazing!”
12. THE SUCK AND BLOW SCENE REQUIRED SOME MOVIE MAGIC.
While "Suck and Blow" might have seemed like a fun and sexy party game, it was in fact a pain to shoot. Turns out the cast wasn't up to sucking or blowing well enough to make the game work with an actual credit card. So a prop card made of cardboard was brought in. When that failed, generous amounts of ChapStick were applied to the cast's lips to make the card stick. Less sexy now, huh?
13. THE GOLDEN GIRLS PAID TRIBUTE.
At the 1996 MTV Movie Awards, Clueless was spoofed by Estelle Getty, Rue McClanahan, and Betty White of The Golden Girls. It was a fitting tribute where these hilarious ladies metaphorically passed the torch to a new batch of sharp comedic performers.
14. CHER IS CLUELESS TO THE MANY HINTS AT CHRISTIAN'S SEXUAL IDENTITY.
Aside from his total lack of interest in making out with Cher, Christian's identity as a "friend of Dorothy" is tipped throughout with various clues. For instance, on movie night he suggests Some Like It Hot and Spartacus, the former being a movie about men cross-dressing, which arguably ends with the creation of a gay coupling. The latter includes a scene where Laurence Olivier's character attempts to seduce Tony Curtis's. Christian is also spotted reading Junkie by William S. Burroughs, an acclaimed and gay American writer. Lastly, Cher's chances of romance with Christian are spelled out in his intro, where a headline posted on a board next to him reads, "On The Road To Nowhere." Way harsh.
15. HECKERLING HAS A CLUELESS CAMEO.
Blink and you'll miss her, but Clueless's writer-director wedged herself into the final scene at the wedding of Mr. Hall and Miss Geist. She's one of the non-teen bridesmaids battling Cher for the bouquet.
16. CLUELESS IS PART OF AN UNOFFICIAL TRILOGY.
Heckerling is well known for her forays into coming-of-age stories: The first was her directorial debut, the beloved 1982 comedy Fast Times At Ridgemont High. Clueless came in 1995 was followed up with the Jason Biggs-fronted Loser in 2000, Each comedy not only centered on teens, but also aimed to capture the adolescent zeitgeist of their eras in a way that made them accessible and cool to all ages. Obviously, some worked better than others.
17. JEREMY SISTO TRIED TO KILL ALICIA SILVERSTONE (IN A MOVIE).
That's right. Just before production got going on Clueless, Sisto (who played Elton) and Silverstone co-starred in Hideaway, a thriller in which Sisto plays a devil-worshipping killer stalking Silverstone's character. Sisto would later go on to audition for Titanic. Of course, we all know he lost out to Leonardo DiCaprio, but his screen test has survived:
18. SUBURGATORY FEATURED A CLUELESS REUNION.
From 2011 to 2014, Sisto co-starred in the sitcom Suburgatory, where he had a chance to reconnect with a pair of Clueless cast members. Heckerling helmed an episode of the series, titled "Victor Ha." And in 2012, Silverstone had a four-episode arc as Eden, an ex-girlfriend of Sisto's character.
19. HECKERLING AND SILVERSTONE RE-TEAMED FOR A VAMPIRE COMEDY.
In 2012, Heckerling and Silverstone brought a reunion of their own to theaters with Vamps, a rom-com about two sexy vampire ladies with love troubles. Unfortunately, the film did not do well. It flopped at the box office, pulling in just $3,361, and its reviews were mixed.
20. MR. HALL WAS BASED ON TWO REAL TEACHERS.
To play the debate teacher Mr. Hall, Wallace Shawn pulled from his own experience, having been a professional teacher before he went into acting full-time. But Shawn's character got his name from Herb Hall, the actual debate teacher of a Beverly Hills high school at the time. The real Hall was a friend of Heckerling's, and got to appear in Clueless as the school principal.
21. CLUELESS WAS ORIGINALLY PITCHED AS A TV SERIES.
No, it wasn't the TV-spinoff of the popular movie. Back in the early '90s, 20th Century Fox was shopping for a sitcom about cool teenagers (no nerds). So Heckerling pitched them No Worries, which she had conceived with eventual Clueless producer/Miss Geist, Twink Caplan. But Fox feared no one would care about a show with so many girls, so Heckerling went back to the drawing board, reshaping her characters into a feature screenplay with early drafts called I Was A Teenage Teenager and Clueless in California.
22. CLUELESS EVENTUALLY RETURNED TO TV.
One year after the film opened, the Clueless TV show was resurrected. Rachel Blanchard stepped in for Silverstone as Cher, while Elisa Donovan, Donald Faison, and Stacey Dash reprised their roles as Amber, Murray and Dionne, respectively. The series ran for three seasons, wrapping in 1999.