Humanities › Literature Top Three Shakespeare Villains Share Flipboard Email Print John Snelling / Getty Images Literature Plays & Drama Monologues Basics & Advice Playwrights Play & Drama Reviews Improvisation Games and Activities Best Sellers Classic Literature Poetry Quotations Shakespeare Short Stories Children's Books By Wade Bradford Theater Expert M.A., Literature, California State University - Northridge B.A., Creative Writing, California State University - Northridge Wade Bradford, M.A., is an award-winning playwright and theater director. He wrote and directed seven productions for Yorba Linda Civic Light Opera's youth theater. our editorial process Wade Bradford Updated February 02, 2019 While Shakespeare is known for penning many heroic monologues from "Henry V" to "Hamlet", let's turn our attention toward the immortal bard's darker nature. Shakespeare has a knack for giving a sharp tongue to his tyrants, traitors, and antagonists. The following is a list of the three most villainous Shakespeare characters along with their best monologues. #1 Iago from Othello Iago is Shakespeare's most sinister (and in some ways most mysterious) character. He is the main antagonist in "Othello." He is Othello's ensign and the husband of Emilia, who is the attendant of Desdemona, Othello's wife. A Machiavellian conniver, Othello deeply trusts Iago, and Iago uses this trust to betray Othello while still appearing honest. Iago's motives also remain a mystery, leading to lengthy debates between theatergoers and Shakespeare scholars alike. While some argue his motivation is to be promoted, others believe Iago enjoys destruction for the sake of it. In Act II Scene III, Iago delivers one of his most villainous monologues as he reveals his plot to overthrow Othello's sense of reason and trust. He explains his scheme to make it seems as though Othello's wife Desdemona has been unfaithful. Here are some quotes from the monologue that exemplify Iago's manipulative and mysterious nature: "And what's he then that says I play the villain?When this advice is free I give and honest.""How am I then a villainTo counsel Cassio to this parallel course,Directly to his good?""So will I turn her virtue into pitch,And out of her own goodness make the netThat shall enmesh them all." #2 Edmund from King Lear Nicknamed "Edmund the Bastard," Edmund is a character in Shakespeare's tragedy, "King Lear." He is the black sheep of the family, and self-conscious because he believes his father favors the so-called "good brother" over him. On top of that, Edmund is particularly bitter as he was born out of wedlock, meaning his birth was with someone other than his father's wife. In Act I Scene II, Edmund delivers a monologue in which he reveals his intention to make a grab for power that will send the kingdom into a bloody civil war. Here are some memorable lines: "Why bastard? wherefore base?When my dimensions are as well compact,My mind as generous, and my shape as true,As honest madam's issue?""Legitimate Edgar, I must have your land.Our father's love is to the bastard EdmundAs to th' legitimate. Fine word- 'legitimate'!""Well, my legitimate, if this letter speed,And my invention thrive, Edmund the baseShall top th' legitimate. I grow; I prosper.Now, gods, stand up for bastards!" #3 Richard from Richard III Before he can ascend to the throne and become king, the hunchbacked Richard, Duke of Gloucester, does a lot of double-crossing and killing first. In one of his more diabolical moves, he attempts to win the hand of Lady Anne, who at first loathes the power-hungry creep but eventually believes him sincere enough to marry. Unfortunately for her, she is completely wrong, as his villainous monologue in Act I Scene II reveals. The following are excerpts from Richard's speech: "Was ever woman in this humour woo'd?Was ever woman in this humour won?I'll have her; but I will not keep her long.""Hath she forgot already that brave prince,Edward, her lord, whom I, some three months since,Stabb'd in my angry mood at Tewksbury?""My dukedom to a beggarly denier,I do mistake my person all this while:Upon my life, she finds, although I cannot,Myself to be a marvellous proper man."