This book investigates the changing culture of grandparenting. Depending on the group, the period, and the family, grandparents have been powerful patriarchs and matriarchs, reliable second parents, dependents, burdens, or community figures. The book examines the history of grandparenting and the changing depiction of grandparent culture from “old” to “hip,” including the development of the celebrity grandparent, the emergence of media technologies that allow for new communication and relationships between grandparents and their grandchildren, new rituals associated with grandparenting, the growth of the marketing of grandparenting as a new stage of life, and the impact on our culture of the commodification of grandparenting. Prior to the twentieth century, within the United States the idea of the modern grandparent likely did not even exist. Many people did not live long enough to reach the grandparent stage of life. Today, people are living longer, and grandparenting is occupying a longer phase in one’s life. Grandparenting is becoming its own life stage, where new rituals exclusive to grandparents are emerging. Newer technologies, such as Skype, Google Hangout and FaceTime, allow grandparents who are far away to establish relationships with their children. Many grandparents also use social media and blogs to chronicle their experiences. Some grandparents have turned their grandparent lifestyle into a business. The representation of grandparenting in popular culture is shifting as well. Grandparents are becoming their own figures on television and film programs, including reality shows. Others have been thrust into the public eye across social media. Marketers have realized the power of this new consumer subgroup and have begun to direct marketing campaigns to grandparents. Yet, despite the pervasive images of grandparents, some of which present empowered figures, grandparent representation in popular media continues to mimic many of the stereotypes commonly associated with aging, encouraging people to laugh at versus laugh with these figures. The Third Act: Grandparenting in a Digital Age examines grandparenting through history, interviews, and popular culture to study the changing image of grandparents in society.