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This thesis examines three of Shakespeare’s plays in light of his engagement with the late Elizabethan Inns of Court. It considers the cultural, pedagogical, and intellectual world of the Inns and their impact on the emerging dramatic industry in the late sixteenth and early seventeenth centuries. Each of the three main chapters explores one of Shakespeare’s plays that was either performed at one of the Inns of Court (The Comedy of Errors and Twelfth Night), or otherwise considered to have been performed there (Troilus and Cressida). By looking at Shakespeare’s Inns of Court plays collectively, the thesis will seek to elucidate how their design complements the unique performance context of the Inns of Court revels, and the ways in which these works reflect or contemplate the Innsman’s social, political, and professional realities. The latter two chapters draw comparisons between Shakespeare’s relationship with the Inns and that of his contemporary, Ben Jonson, whose early satires were heavily indebted to literary fashions cultivated at these institutions. Ultimately, the thesis attempts to demonstrate the diverse strategies Shakespeare implemented in these plays in order to entertain, and to provoke, one of the most important and influential sectors of his audience.