The evolution of the resident assistant position and its history are important to understanding its increasing complexities. In this article we examine how court cases and federal legislation, along with changes in popular culture, have altered and shaped the role of the resident assistant. Our premise is that this role, originally relatively straightforward, has evolved into a multifaceted set of responsibilities that are increasingly complicated by court decisions and federal and state legislation. This has corresponding effects on residence life and housing programs in the training and supervision of staff at all levels. [Discussion questions were prepared by Bobby Roberts and Olivia Vernon.]