Role-plays in a virtual world hold tremendous potential for higher education because they allow synchronous, immersive participation by students located across the globe. They also have the added advantage of allowing students to adopt roles and carry out tasks that are not possible in the real world. In this article, a project that involved pre-service teachers carrying out role-plays based on de Bono's "Six Thinking Hats" framework is presented. A pilot study was carried out over two years with on-campus students, who performed the role-plays both in a real-life, physical setting and within the virtual world of "Second Life." The activity has since been extended to off-campus students exclusively using "Second Life." The authors report selected quantitative and qualitative survey data from the pilot study that provide insight into students' perceptions of this style of learning, and discuss the challenges that were encountered and how they were overcome. The future of virtual world-based role-playing as a strategy for teaching and learning is discussed, with a focus on its application to distance education contexts. (Contains 3 tables and 4 figures.)