2. Dolores Umbridge (Imelda Staunton) in 'Harry Potter and the Order of the Phoenix'

Was there ever a more cringe-inducing, superior smirk than the one worn by Professor Umbridge? The fact that that she wears it along with cutesy pink suits and pearls makes it all the more unbearable. The other villains in the Harry Potter universe may be more dangerous and grandiose, but when evil wears such a simpering smile, it's far more disturbing.