During the early modern period in England, profound changes in socio-economic attitudes transpired as feudal values gave way to those of nascent capitalism. The literature of the era reflected this transition as some authors wrote panegyrics to the mercantile ethos, while others satirized the mercenary tendencies they perceived around them. Considering the volume of work Shakespeare produced, it is perhaps surprising that so few of his plays directly concern money and confront what might be termed "the monetary mindset." The five plays that did so, The Comedy of Errors, The Merry Wives of Windsor, The Merchant of Venice, Measure for Measure and Timon of Athens (co-authored with Middleton), constitute a distinct sub-group within the Shakespearean canon and are the focus of this dissertation. Over the course of these four comedies and single tragedy, Shakespeare's view of how economic determinants influence and shape interpersonal relationships seems to darken progressively, suggesting a growing discomfort with the financial way of the world. This is powerfully communicated by the evolution of this thematic concern; what starts out in farce culminates in nihilistic tragedy.Working within the critical stream of new economic criticism, this dissertation uses formal analysis to interrogate the linguistic structures and strategies of these plays. What is central to this thesis is how words are used ---how fiscal language recurs to form metaphoric patterns, how words associated with the quantifiable dealings of commerce transform into signifiers of qualitative values and how the endemic employment of discursive tropes based on mercantile principles debases interpersonal relationships. These plays, perhaps because of their relative singularity in Shakespeare's oeuvre, have a dialogic relationship with one another and their generic confreres that further informs my arguments. In addition, Quarto-Folio discrepancies regarding fiscal references in Merry Wives, as well as the divergent authorial agendas of Shakespeare and Middleton in Timon , are subject to critical scrutiny. Finally, close textual readings are complemented by broad-based historical contextualizations through which I correlate dramatic concerns to early modern socioeconomic ones because it seems apparent that the societies depicted in these five plays reflect the changing world in which Shakespeare lived and wrote.