What-ever! Clueless was the film we all grew up with but this week, it’s been revealed that it may not have turned out quite as it did. According to the casting directors, a number of different actresses were up for the role of Cher and apparently, Reese Witherspoon was closest to landing the part. Angelina Jolie and Gwyneth Paltrow were also said to be in the running at the time. “I met with Reese [Witherspoon] because everyone said, ‘This girl’s amazing. She’s going to be huge’,” said Amy Heckerling, writer and director. “I saw some movie where she had a southern accent. Maybe it was on TV, a movie of the week. But I did see some scenes of hers and went, ‘Wow! She’s amazing!’ But Alicia is Cher." “There was something about Alicia that was a little bit younger and a little bit more naïve in a way that we felt was really the right girl.” Not only that, but Heckerling also revealed that Ben Afleck was originally meant to play the role of Josh. To be honest, we don’t see how anyone but Paul Rudd could play that part!