Ireland had been a British colony for centuries and during these centuries the number of colonial stereotypes, both negative and positive ones, about the Irish increased. Irish people, mainly after became deprived of self-government and self-representation by the English, began to rebel against their colonisers by inverting positive stereotypes. Irish nationalist movements against English rule started to strenghten during the nineteenth century with the aim to repossess self-representation.This process of wrestling representation from the coloniser is allegorised on the stage by John Millington Synge,the most enduring playwright of the Celtic Revival at the turn of the nineteenth and twentieth century. His play, The Playboy of the Western World (1907), revolves around the struggle for self-representation. Martin McDonagh’s play, The Cripple of Inishmaan (1996), written almost a hundred years later but set in 1934, in a freshly emerged post-independence Ireland, also focuses on this central issue. In both plays the main theme is the protagonists’ changing self-image: from oppressed, degraded figures they become self-confident men capable of standing up for themselves. The two main characters,’ Christy’s and Billy’s advancement can be read as metaphorical of how Ireland fought against being oppressed and represented by the English in the nineteenth century.