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Artificial intelligence (AI) tools like AI chatbots or AI virtual assistants are opening new avenues for experiential learning in sociology and criminology classrooms. This roundtable presentation explores the use of AI tools to simulate interviews with influential historical and contemporary figures in the field of criminology—including theorists, policymakers, practitioners, and formerly incarcerated individuals. By crafting structured dialogues with AI-generated personas such as Cesare Beccaria, Edwin Sutherland, Angela Davis, W.E.B. Du Bois or modern-day correctional officers, students engage more deeply with theoretical frameworks, policy debates, and lived experiences. Implemented in undergraduate courses, the activity encourages critical thinking, improves student understanding of criminological and sociological perspectives, and fosters empathy. Preliminary results from classroom applications show increased student participation and a deeper connection to course material. The session will discuss pedagogical design, ethical considerations, student feedback, and limitations of using AI in this context. This innovative approach provides a scalable and adaptable tool for instructors seeking to enrich their curriculum through interactive, reflective learning experiences.