This thesis provides a comparative analysis of two plays written by the famous Irish playwright George Bernard Shaw. Pygmalion and Major Barbara are both set against the backdrop of early twentieth-century England. Having emigrated from Ireland to England, Shaw is uniquely predisposed to noticing the social issues plaguing British society; issues that are imperceptible to those who do not have the benefit of Shaw’s outsider gaze. This thesis analyzes the state of society presented in the two plays by exploring the differing perspectives of Shaw’s characters, with the goal of providing insight into Shaw’s understanding of poverty and its potential solutions. Shaw’s essays The Quintessence of Ibsenism, his sermon The New Theology, and his non-fiction book The Intelligent Woman’s Guide to Socialism and Capitalism are used to explore the author’s personal beliefs, insofar as they are relevant for a more complete understanding of the ideologies espoused by his characters. Furthermore, the relationships between creator and creation present throughout the two plays are explored with the goal of understanding the significance of the Pygmalion myth in Shaw’s work. Special focus is also directed to the theme of the soul, specifically the concept of selling one's soul, as the role of Faust is shown to perpetuate the problem of poverty. This thesis concludes that the experiences of Shaw’s cast of characters form a collection of cautionary tales about how not to enact societal change, specifically regarding solving poverty. Charity, religion, capitalism, and the attainment of culture all ultimately fail to cause lasting change because they only deal with the surface problems of poverty. The only workable method left, one that is heavily alluded to by Shaw but never brought to fruition on the pages of his plays, is a revolution focused at changing the structural problems of society, because the foundations of the class system facilitate poverty.