In William Shakespeare's Elizabethan plays, role-play is capable of the highest form of empowerment for its players: possession of the monarchy. The ability of theatrics to empower, or even cause, a fictitious monarch resonated with Shakespeare's Elizabethan audience, whose own monarch, Queen Elizabeth, shamelessly embraced and exploited this ability. However, while virtually all of Shakespeare's plays possess the potential for role-play's ultimate empowerment, the extent to which his characters are able to achieve this potential varies. In this essay I examine the varying successes with which Shakespeare's characters attempt to use role-play as a means of gaining a monarchy. I begin by discussing the successful manipulation of role-play and improvisation by Prince Hal and King Henry in I Henry IV. Secondly, I discuss Claudius' ability to gain a monarchy by representing King Hamlet and inability to maintain it by failing to control his own representation in Hamlet. Finally, I discuss Julius Caesar's use of theatrics to create a monarchy for himself where one does not previously exist, and the failure of his assassins to control their own representation. By comparing these scenes in I Henry IV, Julius Caesar, and Hamlet to Elizabeth's own manipulation of her representation, I argue that the extent to which role-play is a form of empowerment in Shakespeare's plays is subject to constraints similar to those present in Elizabethan society.