The rapid proliferation of better-quality “prosumer” equipment and of powerful yet inexpensive editing software has helped erode the long-standing distinction between professional media producers and amateurs. Today’s aspiring young artists can take existing film, musical works, and other audiovisual material and transform them in varying degrees to create new work that comments on the world around them and that rivals in quality much of what Hollywood and professional musicians produce. However, this assessment is from the point of view of content. The looming specter of aggressive copyright policing by a litigious creative industry still divides the haves from the have-nots. Industry monitors have been able to conduct mass takedowns of work they deem to be derived from their own, as provided for by the 1998 Digital Millennium Copyright Act (DMCA). Both preservice teachers and aspiring media professionals must pay close attention to the copyright implications of creative work they choose to appropriate. They must take especial care that the work they find for secondary manipulation and reframing meets the standards for fair use and transformation as provided in the Copyright Act. In this chapter, we discuss the concept of transformation and how to best use its freedoms and assess its limits in the creation of new digital media objects and creative classroom tools.