Madness in Shakespearean plays has distinct and multiple meanings and purposes. On one level, the madness of insanity is clearly felt in the tragedies like “Lear”. On another, madness is also felt in the frenetic pace of impossible situations and comedic errors in judgment as is found in “Twelfth Night”. Madness is, then, both tragic and comedic. But, it is much more than that. Madness represents a loss of control, of being borne by unnatural impulses, drivesa nd, perhaps, voices. Being mad is to not be yourself, it is to have lost touch with humanity, with life and with reality. The mad are excused from the rules of man and at the same time, tragically bound by them. For some, in madness is found freedom. Lear is wrapped, tightly, within a horrible prison created by his inability to see through the duplicitous daughters and embrace the one person in his life that loves him enough to refuse him. His madness, in the end, is what sets him free of the binds that his daughters and his pride had him in. The madness, however, is like the release from an intense and long-term drug addiction, it is horrible to watch, but leaves Lear in a better state afterward, free of poisons. Madness also allows otherwise straight-laced, bound by social rules (which were oppressive in Elizabethan England), to freely express inner passions, make mistakes and be fools in the eyes of others without fear of recourse, as is the case with nearly every character in “Twelfth Night”. It is the purpose of this paper to examine the nature of madness in the Shakespearean context, how it plays out in both King Lear and Twelfth Night, and the meaning behind the madness in both works.