5 Things We Learned About Clueless From Vanity Fair’s 20th Anniversary Feature

Clueless turns 20 years old next month. 20 years since Cher failed her driving test. 20 years since “Rollin’ with the homies.” 20 years since Sporadicus. 20 years since “I love Josh!” 20 years and Paul Rudd still hasn’t aged a single day.

In honor of this wonderful anniversary, Vanity Fair magazine has released a new feature titled “The Definitive Oral History of How Clueless Became an Iconic 90s Classic.” It’s an excerpt from a new book by Jen Chaney titled As If! (out next month) that features interviews with writer/director Amy Heckerling and the movie’s cast and crew. Reading the excerpt revealed some fun facts, so I went ahead and rounded up my favorites to share with you.

1. It started out as a TV show.

Amy Heckerling started developing a show called No Worries (one of many names) in 1993 that eventually became the movie Clueless we know today. But the road to making the movie wasn’t easy, and Heckerling faced a number of rejections and suggested changes. That included a request to make Josh Cher’s neighbor instead of step-brother, because Fox thought it was “incestuous.”

2. A number of famous actresses were considered for Cher.

That included Alicia Witt, Tiffani Thiessen, Keri Russell, Gwyneth Paltrow, Angelina Jolie and Reese Witherspoon. But Heckerling had her heart set on Alicia Silverstone, who at that time was relatively unknown, besides an Aerosmith video and a movie called The Crush.

3. Paul Rudd took a really long time to be cast.

So long, in fact, that he got a part in Halloween: The Curse of Michael Myers (his first movie) and cut all his hair off on a whim — only to run into Amy Heckerling and find out he was still in the running. Paul was a lot more enthusiastic about Clueless:

“I don’t remember the actual call saying I got the part…. I wasn’t sure about [Halloween]. But Clueless: no, I wanted to do that one.”

Thank goodness for that.

4. Seth Green and his girlfriend almost played Travis and Tai.

Seth and Breckin Meyer were the top two choices for Travis… and they happened to be BFFs. Seth’s then-girlfriend Alanna Ubach was considered for Tai. Neither of them were cast, of course, but what a scrapbook of their relationship that would have been.

5. Stacey Dash almost got hit by a car when she found out she was cast.

Here’s what she says happened:

“I was crossing the street [in L.A.]. I’ll never forget it. I got the phone call that I got the job, and I almost got hit by a car. I was just jumping up and down in the middle of the street, screaming because I was so excited.”

A cell phone in the ’90s? I guess she was an early adopter.

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