Feigned madness is a motif that – with varying frequency – returns in literary texts. It is usually a carrier of important metaphors, such as: search for truth, escape from reality or conscious rejection of routine. Moreover, it seems to have an exceptional interpretative potential in dramas as it also symbolises a performative treatment of existence and an awareness of fiction which directs the poetics of the drama towards the meta-theatre. The author of this article considers these issues in relation to the titular characters of two dramatic masterpieces of world literature: Hamlet by William Shakespeare and Henry IV by Luigi Pirandello. Both characters, for various reasons, decide to hide their true psychological condition under the image of a madman, which, interestingly, confirms their sophistication and intellect. Putting on the mask of a madman guarantees the privilege of unpunished violation of conventions and established orders, hated by individuals such as Hamlet or Henry IV. This rebellion and emancipation lead to the final defeat of these characters, who, however, dominate over the others, since, unlike other actors who dispassionately play roles that have been imposed to them, they choose their roles, and – most importantly – they are aware that they are playing.