4. Villain  Iago
I don’t think there’s a greater, more malevolent, unrepentant, intelligent, repulsive, inscrutable, or fascinating villain in Shakespeare or in fiction than Iago. It’s not what he does to his enemies but to his friends that is so frightening. He destroys others from the inside out, using their flaws or virtues against them. A devil figure and a textbook psychopath, Iago is both endlessly cunning and mundane. The audience never witnesses his death or gets a satisfying explanation for why he led his comrades into spectacular disaster.
4. Villain  Richard III
Scholars consider Richard III to be one of the most maligned figures in history, thanks in large part to Shakespeare’s dynamic creation. This Richard III ruthlessly kills his way to the throne, playing with victims as he goes. He is despicable, yet he seduces audiences with his brilliance and wicked sense of humor. Unfortunately, we eventually realize that he has also duped us. Once king, Richard becomes a paranoid despot, revealing himself as nothing more than an empty, lonely mad man.
4. Villain  Aaron
In a play filled with heinous individuals, Aaron the Moor stands out as the most cunning and sadistic. Though he refuses to repent and delivers epic speeches about reveling in depravity, his position as a slave and his love for his infant son are points of sympathy. Aaron is one of Shakespeare’s most charismatic and evil characters.
4. Villain  Shylock
Shylock is one of Shakespeare’s most written about and most controversial characters. Both an antisemitic charicature and a sympathetic figure, Shylock craves money and blood and gives stirring speeches about the mistreatment of Jews. He has been used in arguments defending and condemning bigotry. Ultimately a bitter, sad, and vengeful man, ill-treatment has warped Shylock’s humanity. He is a reminder of prejudices present in Shakespeare’s time and now.