The paper provides an insight in the retrogression of the protagonist King Lear from the play King Lear written by Shakespeare. It deals with a critical analysis of the evolution of madness or as we say insanity that the character occupies in the play. We begin with a concise diegesis of the plot line and how things transpire for the protagonist King Lear followed by detailed analysis of the instances that lead us to conclude that King Lear is a veritable example of “Reason in madness and madness in reason” as asserted by Shakespeare himself to be the leitmotif of the play. The discussion is centralised on Lear and his actions along with multiple lines and quotes from the actual play. We endeavour to prove our point that indeed it was King Lear only who because of his arrogance driven insanity led himself and his kingdom to ruins. Insanity is a recurring thread in the play and is associated with both disorder and hidden wisdom. Even the advise provided by few wise characters in the play seem mad babble rather a sage counsel. In the latter parts of the play when lear descends into madness, his turmoil and mind reflect the chaos that unfurls across the kingdom, which was once his. It’s only when he has lost all sane thought that he learns to be humble.