During the last two decades of the twentieth century, theatre director Lloyd Richards, and playwright August Wilson, two uniquely talented black men, did something in the American theatre that had never been done before. They collaborated on six plays, written by Wilson and directed by Richards, which were ultimately produced on Broadway. This dissertation examines their collaboration on the development and productions of the first three plays. Through a performance analysis of each production and a close critical analysis of the texts, this dissertation will critically examine the sociopolitical, economic, and cultural forces that influenced Richards and Wilson. My dissertation will argue that it was Richards' directing style, his understanding of the artistic process, and the power of performance that contributed greatly to the success of Wilson’s first three plays on Broadway. It also argues that Richards’ successes in the theatre and his achievements in the academic world were no accident, but the result of his background, his preparedness, his unique forethought, and his belief in hard work. It is my premise that the contributions made by Richards to the theatre, to the development of playwrights, and to the training of theatre artists have not yet been fully examined. In addition, his contributions played a major role in the success of Wilson’s Twentieth-Century Cycle of plays. By the process of a thorough investigation of the three Broadway productions, and an examination of the forces and conditions that shaped Wilson’s and Richards’ personal and professional identities, this dissertation will help to illuminate Richards’s and Wilson’s significant contributions to the theatre.