In Shakespeare’s Othello and King Lear, the protagonists Othello and King Lear face similar struggles in acknowledging and accepting their insecurities. Othello the Moor is doubtful and jealous in nature, which is triggered by his wife’s alleged adultery, whilst King Lear is old and dependent on the affection he demands from others. Upon first glance, it is easy to distinguish the roles of the protagonists in each play as they both possess distinct characteristics of tragic heroes. However, if one examines these characters further, a deeper significance to the plays may come to light. For instance, a common misconception in society is that the expression of emotions attribute vulnerable and feeble qualities to men. Granted, both Othello and King Lear reduce their emotions to what is deemed to be socially acceptable for men, namely rage, throughout these two works. But in fear of exposing their insecurities, Othello and King Lear are compelled to mask their emotions and ultimately undergo a loss of self-identity for the sake of ‘masculinity’. These findings then aid in formulating one research question: How does Shakespeare use tragic heroes to criticize the social constructs of masculinity? This question may be answered through the analysis of the elements of a tragic hero. Firstly, one’s preeminence in society lays the foundations of an archetypal tragic hero, as one’s noble actions early in the play highlight the resulting downfall of a character. Another component must be a hero’s tragic flaw, a defect or weakness a character possesses, that inevitably leads to his downfall. Lastly, the realization of the tragic hero’s flaw at a time of irreversible fate evokes catharsis, feelings of emotional purgation, from the audience. Thus, in deconstructing the characteristics of tragic heroes in both Othello and King Lear, Shakespeare re-establishes the ideals of masculinity to alleviate the social constructs placed on men. With thorough exploration of these two timeless works, one is able to delve beneath the traditional elements of Shakespearean tragedies and apply modern criticism on the unchanging nature of human beings. Hence, one may come to appreciate Shakespeare’s attempts to redefine the rigid definition of masculinity. As there are multiple facets in the workings of a tragic hero, more emphasis will be placed on specific features of a tragic hero and its relations with and effects on masculinity rather than an a generalized view on the topic as a whole.