Abstract: This paper describes an ongoing interdisciplinary and collaborative project between the College of Education and the College of Arts and Sciences that utilizes online role play as a way to teach Shakespeare to pre-service and in-service teachers. While distance instruction is the project's primary objective, of equal importance is the desire to model online role play as a teaching strategy in virtual learning environments. This paper describes the project's activities and provides data gathered from its discussion forums, chat sessions, and various forms of student assessment. Teaching Shakespeare, or any historical figure using role play in virtual learning environments, has its advantages and limitations, as well as the significant theoretical challenges. Those instructors interested in using role play as a teaching strategy in the content areas of literature, history to enhance teaching will find these advantages, limitations, and theoretical helpful in planning role play sessions in virtual learning environments.