This study investigates the bully and the bullied from 1950 to 2010. It begins by presenting a historical background of each decade with the major historical events that defined our culture. Each decade can be characterized by a particular zeitgeist, or spirit of the times. During each decade, popular movies and television programs that provided bullying as entertainment will be examined. This study will explore how popular culture was concurrent with bullying. This study through Barbara Coloroso's (2008) explicit characteristics of the bully and the bullied will describe the characteristics of the bully and the bullied from each decade from 1950 to 2010. The dissertation answers six questions for three time periods; the characteristics of the bully, the characteristics of the bullied, as defined by Barbara Coloroso's (2008) characteristics--how popular culture portrayed the bully and the bullied, how bullying was being manifested in schools, policies and procedures in Illinois K-12 school districts that emerged to address bullying, and the implications for educational leadership. Key researchers' findings, movies, television programs, and legislation, in bullying were utilized in this study as primary sources. The early works of Dan Olweus (1993), Ken Rigby (1996), and the writings of Barbara Coloroso (2008) served as valuable resources. Secondary documents used in this study included journal and magazine articles, newspaper articles, movie reviews, books, and websites. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]