This study compares two stage villains--Quomodo in Michaelmas Term and Iago in Othello--in their unparalleled genius of “dramaturgy.” They are playwright-characteristers: They dramatize roles for themselves or for others, create mini-plays to deceive others, and improvise action with any available resources. Quomodo lies, cheats, plays tricks, and disregards morality and conscience in order to seize a piece of land from a young gallant Esay. He dupes the latter with a commodity scam, which involves cunning operations of polts, disguises and traps. Iago, in an even more sophisticate way, carefully and calculatingly composes scripts for all of his fellow characters. He manipulates the illusion to the extent that it becomes reality for Othello, who is taken in by false appearance and smothers Desdemona in fits of jealousy and rage initiated and intensified by the malicious show staged by Iago. Both plays highlight the dialectic of illusion and reality, imagination and truth. They reveal the artificial construction of meaning. In addition, drawing on Lacanian theory of the subject of lack, I would like to point out that these tricksters' manipulations of others mark out their desire and lack. To temporarily fill up the hole of lack, they acquire some satisfaction from the sheer pleasure of invention and construction of plots and of seeing how they work. It is a Jouissance of form, which is charged with erotic dynamics and repetition compulsion. But they are doomed to encounter their void and lack because they take the Lacanian object a to be a stand-in for the lost object that satisfies their desire.