Here’s What You Never Knew About The Clueless Film

As every Clueless fan knows, it’s the film’s 20th anniversary next month. Yep, 20 YEARS. We feel old.

And in honour of this milestone occasion, the film’s writers and casting directors have given the most epic interview to Vanity Fair in which they reveal what you definitely *didn’t* know about Clueless.




Speaking about who nearly got cast for the role of Cher Horowitz, director and writer Amy Heckerling and Carrie Frazier revealed not only was Gwyneth Paltrow considered, but also Angelina Jolie and Reese Witherspoon. We mean, can you imagine?!

‘It was the first time I’d seen Angelina Jolie… But she was too knowing for what was needed for Clueless,’ Frazier said. ‘Angelina never came in [to audition] for the project. I was just looking at her tape. I remember an agent pitching her, and I’m going, “No, no, no, this is exactly the opposite of what I need for this.”‘ 



‘I met with Reese [Witherspoon] because everyone said, “This girl’s amazing. She’s going to be huge,'” Heckerling said of Reese, who made it big in Cruel Intentions just a few years later.

But it wasn’t meant to be. ‘I had my heart set on Alicia [Silverstone]’, Heckerling added. ‘Alicia is Cher.’ We couldn’t agree more. 



And as for Josh, who was played perfectly by Paul Rudd, well – he had stiff competition from a leading A-list actor of the time. 

‘I brought in Ben Affleck, for the role of Josh,’ Frazier revealed. ‘I thought he would be fabulous for it. I was really trying to get Ben Affleck the part.’



‘I’m fairly sure Zach Braff read for Josh,’ Cross added. ‘I had hired a casting director in Chicago to put people on tape for the role while I was still searching for an actor to play the role. He was going to [Northwestern] at the time. My note was that he was good.’

Thankfully, Paul won in the end, due to his and Alicia’s chemistry during the screen test. ‘He really was good with her’, Cross added.

Who knew the road to casting Clueless was such a starry one?!