Clueless is, of course, based loosely on Jane Austen's classic novel Emma. The book — and its 1996 movie adaptation starring Gwyneth Paltrow — centres on a wealthy young woman who passes her time by trying to neatly arrange the lives of everyone around her, all while being, well, clueless to her own feelings and the effects of her meddling. This late '90s period dramedy stays mostly true to the novel with just a few cuts and condensed storylines here and there. It's a gauzy, dreamy, and (of course) romantic movie that's perfect for Clueless fans looking for more about where it all began.