Annie Wilkes- Misery
This lady is the reason an entire generation doesn't pick up hitchhikers. Words for the wise, never become a writer if you fear getting captured and having your legs broken by a superfan. Even though she is violent, malicious, and generally evil, Annie Wilkes has an unmistakable great sense of style.
Dolores Umbridge- Harry Potter
Why does Delores Umbridge care so much about order and rules? Well, that helps her maintain a semblance of control and power over the people around her! Never follow a leader that denounces danger because they choose not to believe in it, especially when that danger is an evil, world-ending wizard named Voldemort.