In the Spring of 2000, Ruth Meyerowitz and Christine Zinni began collaborative efforts--inside and outside of academia--to enhance a course on The History of Working Women at SUNY Buffalo. Videotaping the oral histories of women labor leaders, they later teamed up with Michael Frisch and Randforce Associates--a research group at SUNY at Buffalo's technology incubator--staff at the Educational Technology Center, and The Uncrowned Queens Institute for Research and Education, Inc. to input and present diverse voices of working women into a new media program called "Interclipper." To the group's knowledge, this was the first attempt to apply this new software technology in a university classroom setting for a course on labor history. Rendering oral histories as primary sources of service in the classroom, the new media format provided students with an alternative lens on working women's experiences--perspectives not normally gained in traditional text-based history courses. In the following narrative dialogue, Meyerowitz and Zinni trace the process and progress of their experiences with these technological applications for oral history use over 7 years time. Strengthening collaborative and decentralized aspects of classroom activities by allowing for more personal choices, involvement with the material(s) and active learning, the authors submit a multi-media, multi-perspectival approach to oral history intensified emergent and dialogical qualities of classroom interactions for students, instructors, and interviewees alike. (Contains 3 figures.)