“Exactly the opposite”: the iconic 1990s role Angelina Jolie was “too knowing” to play
There are certain cultural moments that feel so significant, so foundational to who we are, that it seems as though a single different choice could have altered the course of history.
It might feel like a lot of weight to put on the shoulders of a silly comedy, but I genuinely believe the potential timeline in which Angelina Jolie played Cher in Clueless would’ve been the opening of a totally different world.
It sounds like the kind of wild casting decision that could have sent everything into chaos. But looking around, chaos already feels like the norm, so maybe Jolie could have changed it all. Still, after decades of that iconic yellow checked suit living on in photos, and with new generations continually rediscovering and obsessing over the film, it now feels impossible to imagine anyone other than Alicia Silverstone in the role.
Silverstone epitomises Cher, the rich teenage girl up in Beverly Hills. As the film serves as a modern adaptation of Emma, the actor also epitomises that titular character Jane Austen wrote all the way back in the 1810s, telling the tale of a middle-class popular girl on a mission to do ‘good deeds’ to perhaps write one of the most famous complex women in literary history.
The whole point is that Emma, and therefore Cher, is both utterly unlikable yet has your affection anyway. She’s light yet with a clear dark side, sweet yet with cruelty, bright yet plays dumb sometimes. She’s 3D and flawed, and at the end of the day, you’re charmed by her. In the 1995 film, Silverston plays that perfectly as her Cher looks sweet as a button, but plays on a coquettish line of faux-sweetness to get what she wants.
There’s something about casting Angelina Jolie, who’s made a career out of playing baddies and badasses, that doesn’t work for the role.
Casting director Carrie Frazier remembered Jolie’s self-tape for the role as she was one of the many stars considered, including Gwyneth Paltrow and Reese Witherspoon. It was the first time she’d ever even laid eyes on her, and as the story always seems to go when someone first encountered her, she was struck.
However, she knew Jolie wasn’t right for Cher. “She was too knowing for what was needed for Clueless,” she said, as her look seemed too introspective, too mature and too edgy for the role. She explained, “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’.”
But, later down the line, when a role that required that inner depth and darkness came up, Frazier called Jolie instantly. “Later on, when I started heading up the casting department for HBO, and I got the script for Gia, I said, ‘I’ve got the girl’. That was Angelina,” she said, immediately knowing who to call to play the struggling model, buckling under addiction and the weight of her inner world.
