Page takes just the perfect sample monologues from various characters/plays for us to appreciate Shakespeare’s journey into darkness.  Page also alludes to the complex psychologies, believable backstories, and meaningful motivations of modern-day film and TV villains that have been traced back to the Bard.  It is even possible to see how Shakespeare gave birth to the mindset and behavior of the psychopath long before the term was even coined by modern psychiatry.  

Page also points out a major gap in Shakespeare’s timeline as far as villains are concerned. After Richard, Duke of Gloucester (later Richard III) and Aaron the Moor, he turned his attention to plays like Love’s Labour’s Lost and A Midsummer Night’s Dream, to his sonnets, and to a woman we know only as the Dark Lady. Explains Page: “She may have been Jewish, she may have been a Moor…but whoever she was, she had dark skin, dark hair, and dark eyes—and she rocked Shakespeare’s world—making him fundamentally question his cultural biases.”

Which brings us to Shylock in The Merchant of Venice: Shakespeare could have simply created a Jewish caricature, capitulating to the demands of his “rabidly antisemitic” contemporaries. But instead he chose to challenge his audience. “He’s a villain whose motivation is so clear, whose psychology is so complex, and whose language is so rich that he changes the way we experience villainy itself,” comments Page.

Page also perfectly conjures Malvolio (Twelfth Night), whose narcissism proves his undoing and whose humiliation earns our sympathy; Hamlet’s murderous King Claudius, who shows his humanity, and remorse, in a chapel confession (“My words fly up, my thoughts remain below…”); Measure for Measure’s hypocritical Angelo, demanding the virginity of novice nun Isabella in exchange for her brother’s life; Othello’s Iago, a master manipulator/psychopath who poisons the mind of his so-called friend and instigates a murder-suicide (“He did it all with the power of a lie,” says Page); Gloucester’s illegitimate son Edmund (“Now, gods, stand up for bastards!”) in King Lear; and, of course, the title character of “Shakespeare’s darkest play. A play so steeped in evil that most actors won’t dare to speak its name.” You know the one.