8. Lisa Rowe - Girl, Interrupted (1999)
Yes, the film is ostensibly about Susanna Kaysen (Winona Ryder) and her journey out of the pits of Borderline Personality Disorder, but the character of Lisa Rowe (Angelina Jolie) is much more interesting than the drippy Susanna. Lisa is a bonafide sociopath and she quickly weaves a spell over the impressionable Susanna - getting her to store and trade her medications. They bust out of the hospital and land at poor Daisy Randone's door where Lisa taunts Daisy about her incestuous relationship with her father and her attempts at self mutilation. Daisy hangs herself the next morning and whilst Susanna is horrified, Lisa is more laconic, quipping nonchalantly: "She was looking for an excuse". Susanna is sufficiently frightened into being a good girl and complying with the hospital regime. When Lisa is captured and brought back to the hospital, she targets Susanna with mighty scorn. In a gleeful scene she takes Susanna's journals and reads them out to her fellow patients - all of Susanna's remarks and observations about them. Unfortunately drippy Susanna manages to best Lisa into submission by commenting that she is dead inside and the hospital is the only place she has to go to. Lisa is devastated and breaks down crying. Angelina Jolie is perfect as Lisa - exuding an irresistible combination of poison and charisma. She acts everyone off the screen as she wreaks havoc in the film. Susanna is a very milquetoast heroine and in the end we don't really care what happens to her. Lisa, on the other hand, is an absorbing - if despicable - character.